Ten Months Out Is the New Six

I had landed on Puglia for three airtight reasons: I had never been, I love a write-off, and a seasonal flight from Bari to Mykonos promised an easy connection to our summer in Greece. (That flight has since stopped showing up for 2027, so the current plan involves the fast train to Rome, a night or two there, and an Athens connection, solo, with a toddler. The glamour never stops.) The hotel ask was just as reasonable. Five nights at a traditional Puglian resort with a pool, a playground, and enough restaurants on property that nobody has to get in a car at 7pm with a hungry four-year-old. And the answer was still no, because someone with deeper pockets rented the entire village. This is the property that hosted the G7 in 2024, when world leaders took the whole place for three days. Buyouts are not a fluke there, they are a business model. The professional term for how I felt is demotivated. The real term is worse.

The demand underneath is not a fluke either. At Virtuoso Travel Week this August, the network reported forward bookings one to two years out running about 50 percent ahead of last year, and Puglia alone is up 78 percent. The booking window your clients are used to, the one where January feels early and March feels fine, was built for a market that no longer exists.

Meanwhile your clients are moving in the opposite direction. Ten months is the new six on the supply side, and in their heads three months is the new six, so they sit on the deposit until spring and then expect availability that still matches their budget and their dates. Those are false hopes, and you are the one who inherits them. That gap, between when inventory moves and when clients do, is where good trips die, and closing it is the whole point of what follows.

The July 4th Math Your Clients Have Already Done

Now look at next summer’s calendar the way your clients do. July 4, 2027 falls on a Sunday, which makes Monday the 5th the observed holiday, which means a client who flies out Friday, July 2 and lands home Sunday, July 11 gets nine days in Italy for four vacation days. Tripadvisor named Rome the top trending international destination for this year’s July 4th weekend, and next year the calendar is even kinder. If your clients are so much as whispering about Italy next summer, the first week of July is the week they are whispering about.

These Rates Aren’t Getting Lower

Luxury hotels open their calendars at the floor, and dynamic pricing only climbs from there. Three rules I wish someone had taped to my monitor a decade ago:

1. Rates open at their lowest. The number you see the day a calendar opens is the cheapest that week will ever be.

2. Categories close from the bottom up. Lead-in rooms go first, so waiting costs your client the smart room, not just the smart price.

3. Waiting hurts twice. Every month, the rate is higher and the choice is smaller, at the same time.

Virtuoso’s June numbers say the same thing, with luxury rates up more than 11 percent over last year. By January, the entry categories at the marquee houses are gone and what remains costs more than what your client passed on in September.

So I priced the week of July 3, 2027 across the six destinations your clients ask about most, and everything I found is waiting below:

The 2027 booking countdown. Month by month, what closes when, and the date after which you are apologizing instead of planning.

The rate sheet. 18 hotels across Positano, Capri, Venice, Lake Como, Rome, and Florence, each with the opening rate it is charging right now for the first week of July and the room category to request.

The exact words to send your clients this month. The script that closes the gap between your timeline and theirs, and makes booking now feel like protection instead of pressure.

La Storia is $8 a month, or $80 for the year, and the annual is the one I would pick. The archive alone pays for it before your next client call (the 600-hotel spreadsheet lives back there), and if 2027 is moving this fast, you do not want to research it one month at a time.

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The same lesson arrived from the other direction, too. The request I heard more than any other in my years as a travel advisor started the same way every time: “My friend went to Italy and had the best time. I want to do exactly what they did.” And I understood it. The friend came home glowing, the photos were gorgeous, the restaurant list was already typed up. But the moment I asked a few questions about their interests, their pace, and their family, the friend’s itinerary fell apart in their hands. It was built for someone else. I am sure everyone who posts their trip on Pinterest had a great time. They are not you, and their itinerary was never yours.

That’s the first quiet truth underneath disappointing Italy trips. The second is where they break: at the seams. When friends come home from Italy underwhelmed, the complaints are almost never about the Colosseum. The Airbnb sat in the wrong neighborhood, or had no air conditioning in July. They felt scrambled hauling luggage onto a train, or flustered and frustrated between the rental car counter and every parking garage after it. Or they stayed somewhere wonderful on the first leg, let it set their expectations, and then finished in a subpar property in the destination they’d saved for last, wrong location or missing amenities, and the place they were most excited about got tarnished by the room they slept in. The trip breaks between the highlights, and most of those breaks happen in transit.

The Framework Underneath My Best Trips

But one thing I absolutely nailed, even in the package era: I approached every single trip with the same formula in place. Every trip came out different, and every one was built the same way, and that’s what this article is.

When I look back at the client trips I’m still proud of, the ones where people came home and sent the long thank-you email, they had wildly different destinations, budgets, and travelers, and the same skeleton underneath every one. The trips that work aren’t the ones with the best ideas in them. They’re the ones built in the right order, because the order is what protects the seams. The feeling comes before the region. The math comes before the map. The transportation comes before the hotels. Get the order wrong and you end up decorating a broken frame.

So this week I’m handing over the whole frame. Two weeks ago I gave you the eleven checks I run on a finished first-timer itinerary, and a few of these rules will rhyme with those on purpose, because the audit and the blueprint should agree with each other. What follows is the exact framework, ten rules in the order I applied them to every client trip I’d still put my name on, from the blank page forward.

Behind the paywall today:

The framework itself, all ten rules in the sequence I applied them, so your next itinerary builds in the right direction from the first decision.

The first-leg rule that decides where a trip opens, and why I put the most relaxing destination at the start when everyone else saves it for the finale.

The permission slip, the rule about saying no that protects your reputation more than any booking you’ll ever make.

If you build Italy trips, this is the framework that sits underneath everything else I’ve written here. It’s $8 a month, or $80 for the year, and the annual is less than one client gift. Come on in.

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The route: two nights in Venice, four in Florence, one in Rome. I worked with a travel advisor on it, and she told me, “I know you know Italy very well, but this is more challenging than I would make it if I were designing it for you.” I went in thinking I knew exactly what I was getting myself into. It was my first big trip with a toddler. I did not know what I was getting myself into.

Nothing catastrophic happened. What happened was tension, disjointedness, and the feeling of rushing on a trip that was supposed to be a vacation, and no one books Italy hoping to feel rushed.

The Enemy Is Always Speed

I spent years designing first-timer Italy trips for clients, and the pattern I saw again and again is the one I fell into myself: moving too fast. First-timers want to see everything because they don’t know when they’ll be back. So they stack Venice, Florence, Rome, and sometimes the Amalfi Coast into a single week, and the trip becomes a series of check-ins and checkouts with Italy happening somewhere out the train window.

The cruelest part is that speed punishes you hardest in the places first-timers most want to go. Venice and the Amalfi Coast are wandering places. Their whole essence is relaxation, people watching, and landscape. Rushing through them doesn’t just tire your clients out. It puts the trip at odds with the destinations themselves.

The Question That Fixes It

The fix starts before the map comes out, with one conversation: what feeling do they want to come home with? Do they want to see the most and walk away tired, or is this the vacation they want to savor? There’s no wrong answer, but the route for one looks nothing like the route for the other, and an itinerary designed without that answer is a guess.

That conversation, plus the eleven checks below, is how I keep a first-timer route from breaking. These are route-level checks, the shape of the whole trip rather than any one city, and each one covers a different failure point, because I broke most of these rules myself before I learned to check for them.

Behind the paywall today:

The three-night rule and its real exceptions, including the only situation where I’ll book two nights and the distinction that decides when a stay can be shortened.

The scheduling rule for trip-defining experiences like a private Capri boat day, and why the wrong slot can erase the whole reason your client booked.

The final-night move that turns a throwaway positioning night into a sendoff, including the seaside villa forty minutes from Fiumicino.

If you build Italy for first-timers, this is the checklist that keeps their one shot at a first impression intact. It’s $8 a month, or $80 for the year, and the annual pays for itself the first time a client comes home glowing. Come on in.

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By early afternoon, JR (my fiancé then, my husband now) sat down on the edge of the hotel bed and said the words I still quote to advisors: “I can’t do another tour. Can we please cancel it? I’ll pay for it. I don’t even care, I just want to rest at the hotel spa.”

I canceled the tour. He got his spa afternoon. And I got the lesson that now sits underneath every Rome itinerary I touch.

My First Rome Was Everyone’s Rome

Years before that trip, I went to Rome for the first time with a group, on an itinerary that wasn’t designed with me in mind. It was packed to the gills because I believed, like most people planning their first Rome trip, that packed is what Rome requires. We never slowed down. I never saw a charming street. I came home exhausted and lukewarm on a city I now consider one of the great loves of my traveling life.

Families experience this constantly. The parents book the big sights, stack the days, and come home with kids who never want to hear the word Colosseum again. They walk away not liking Rome, and it’s for a lack of design, not for a lack of charm.

The Paris Problem

Think of it the way you’d think of Paris. If you only went to the Eiffel Tower, you wouldn’t understand what Paris feels like. You’d only know what the sights feel like, which is a different thing entirely.

Rome works the same way. The city your clients fall in love with is still bustling, but it lives in the quiet streets of Trastevere and Monti, in the piazza where they sat doing nothing for an hour, in the aperitivo they didn’t have to rush. An itinerary that never leaves room for that version of Rome sends clients home with photos of monuments and no feeling attached to any of them.

The good news for advisors is that every one of these failures is preventable, and they’re preventable before the itinerary ever leaves your hands. After years of planning Rome for clients and getting it wrong on my own trips first, I now run every Rome itinerary through the same ten checks. The kind of checks that only exist because something broke without them.

Behind the paywall today:

The arrival day protocol that protects your client’s money when flights slip, including the one exception where I let a real reservation stand.

The one-tour rule that would have saved my own Sistine Chapel day, and exactly how I sequence tours now.

The hotel I book steps from Piazza Venezia, the five-star that prices like a four, and the trendy property I stopped placing clients in because of one specific walk.

If you plan Italy for clients, this is the checklist you’ll keep open next to every Rome itinerary you build from now on. It’s $8 a month, or $80 for the year, and the annual works out to less than what one client gift costs you. Come on in.

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Sardinia Is Not the Italy Your Client Is Picturing

Hold onto this before you plan a single day. Sardinia is Italian by passport and its own country by every other measure, with a language, a temperament, a cuisine, and a pace that belong to nowhere else. It is also enormous, the second largest island in the Mediterranean, and the driving is slower than any map admits. So the way clients get Sardinia wrong is almost always the same. They treat it like a quick Italian beach escape, book one hotel, aim for August, and spend the trip in the car wondering where the magic went.

I know this because I am living it. The first thing my own planning taught me was that this island needs a trip of its own, the way Puglia does. The second humbled me. I spent years planning luxury travel for other people, and I still could not simply pick a hotel. I love a historic, boutique property, and the ones full of character kept turning out to be either inland, away from the coast I wanted, or priced well past my range, because so much of Sardinia’s coastal stock is new-build resort. I want a resort, and I do not want an oversized one, and threading style and amenities and budget together here was harder than anywhere I have planned. On the mainland it is obvious. Rome, Florence, and Venice are the hubs, and you can put someone in a walkable hotel just outside the center without a second thought. Sardinia hands you none of that shorthand, and choosing between the glamour of the Costa Smeralda and a more remote base that turned out to be isolated and logistically demanding took hours of study. This is the rare Italian destination where you lean on a strong local partner on the ground rather than hand-build it blind, and it is exactly why the questions below carry so much weight.

Which is exactly why these ten questions matter more here than almost anywhere. Every one of them is a chance to manage an expectation or teach your client something before the deposit clears, because the gap between the Sardinia in their head and the Sardinia on the ground is wide, and closing it early is the whole job.

The Series, and What You Get Every Time

This is the last installment, the one that closes out the series. Every one hands you the high-impact questions for a single Italian destination, the exact ones I would ask before I planned a thing, each with a note on what the answer is telling you, all built to copy straight onto your intake form. The coast, Rome, Venice, Lake Como, Puglia, and Sicily came first, and Sardinia is where it ends, fittingly the one where a client’s assumptions cause the most damage, so every question here is written to catch one before it costs them. With this card the collection is complete, seven destinations, one intake system, all of it behind a single subscription.

Here is exactly what is on the other side of this:

The ten questions I would ask before I planned a day in Sardinia, organized to lift straight onto your intake form, each with a note on what the answer tells you and what it lets you set straight.

The ten cover: whether they are expecting Italy or something all its own, the glamour of the Costa Smeralda against the wild side, the split stay that solves a huge island, how central the beaches are and how the best ones are reached, the slow Blue Zone rhythm versus staying busy, when to go and why fall beats summer, which airport and why the car gets booked early, how much the food matters and what to expect at the table, how much the ancient history and traditions matter, and how the budget shifts with where and when they land.A paid subscription to La Storia is $8 a month, or $80 for the year, which comes out to less than one client gift. The annual is the one I would choose.

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Sicily Is Not the Rest of Italy, and That Is the Point

Sicily is ready for you. It is also less paved and less polished than the mainland, and that gap is exactly what people are chasing when they say they want the real Italy. But the island does not hand it over for free. It asks you to want local over resort, to accept that the roads are slow and small and occasionally terrifying, and to understand that the loveliest corners are the ones you have to work a little to reach.

Here is the line I would put on the wall. Sicily earns its own trip. It is vast and varied enough to be its own country, with a Greek temple in one town, Baroque in the next, an Arab-Norman cathedral in a third, and a volcano over all of it. The client who gives Sicily a dedicated stretch of days comes home changed. The client who treats it like a quick add-on comes home having seen a highway and a hotel.

The Series, and What You Get Every Time

This is the next installment. Every one hands you the high-impact questions for a single Italian destination, the exact ones I would ask before I planned a thing, each with a note on what the answer is telling you, all built to copy straight onto your intake form. The coast, Rome, Venice, Lake Como, and Puglia came first. Sicily is where the fantasy and the reality drift furthest apart, thanks in no small part to what a certain television show did to one hilltop town, so these questions are mostly about closing that gap before your client books it.

Here is exactly what is on the other side of this:

The ten questions I would ask before I planned a day in Sicily, organized to lift straight onto your intake form, each with a note on what the answer tells you.

The ten cover: why Sicily specifically and whether they have any tie to the island, what kind of place they want to be based in and what the word resort means to them, whether Sicily is the whole trip or part of a bigger one, how they picture getting around a big island with slow roads, how much the layered history matters, walkability versus needing a car, how central food is and how they feel about seafood with the eyes still on, how much of the island they want to see, when they are going, and one to ask only if they tell you they want off the beaten path.

A paid subscription to La Storia is $8 a month, or $80 for the year, which comes out to less than one client gift. The annual is the one I would choose.

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Puglia Will Not Be Squeezed In

Puglia has been the up-and-coming region for a while now, and it stays up-and-coming for one reason. It is hard to reach. There is no direct flight from the States, the towns sit far apart from each other, and it sits a long way from everywhere your client already wants to go. So it never quite tips over into the mainstream, which is part of what makes it wonderful and all of what makes it tricky.

Here is the line I would put on the wall. Puglia is not a place you add to a trip. It is the trip. It asks for a dedicated stretch of days, its own set of flights, and a client who wants olive groves and white towns and long roads between them more than they want to check another region off a list. The people who give it that come home talking about it for years. The ones who try to bolt it onto a week in Rome come home wondering what everyone was going on about.

The Series, and What You Get Every Time

This is the next installment. Everyone hands you the high-impact questions for a single Italian destination, the exact ones I would ask before I planned a thing, each with a note on what the answer is telling you, all built to copy straight onto your intake form. The coast, Rome, Venice, and Lake Como came first. Puglia is the first one where the logistics decide whether the trip should happen at all, which is why almost every question here is quietly asking the same thing. Is this client ready to commit to it?

Here is exactly what is on the other side of this:

The ten questions I would ask before I planned a day in Puglia, organized to lift straight onto your intake form, each with a note on what the answer tells you.

The ten cover: what is drawing them and what they are picturing, whether Puglia is the whole trip or a piece of a bigger one, which airport they should fly into and out of, how they feel about driving themselves or paying for a driver every day, whether they want a town at their door or a masseria in the middle of nowhere, whether their days belong at the beach or in the countryside, how much of the region they want to see and how many bases that takes, how they want to eat when dinner is mostly at the property, when they are going, and the pace they are expecting once they learn that nothing here is next door.

A paid subscription to La Storia is $8 a month, or $80 for the year, which comes out to less than one client gift. The annual is the one I would choose.

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Como Is a Dozen Towns, and It Matters Which One

Most people say Lake Como the way they say Positano or Santorini, as if it were a single place with a single feeling. On the ground it is a Y-shaped lake with towns strung all along its arms, each with its own personality, its own pace, and its own answer to how a person will spend their days. Bellagio hums with boutiques and foot traffic. Varenna slows you down with a quiet promenade. A remote villa hotel wraps you in gardens and a boat ride to dinner. Where a client lands changes how much of the lake they see, how much they move, and whether the week feels like a rest or a puzzle. Almost none of that shows up in a photo of blue water and a bowl of pasta.

The Series, and What You Get Every Time

This is the next installment. Every one hands you the high-impact questions for a single Italian destination, the exact ones I would ask before I planned a thing, each with a note on what the answer is telling you, all built to copy straight onto your intake form. The coast, Rome, and Venice came first. Lake Como gets ten, and here almost every one circles a single decision, matching a client to the right stretch of shoreline before they fall for a picture and book the wrong one.

Here is exactly what is on the other side of this:

The ten questions I would ask before I planned a day on Lake Como, organized to lift straight onto your intake form, each with a note on what the answer tells you.

The ten cover: whether they want a remote resort or a town at their doorstep, whether the room needs a lake view, whether they need a pool, whether they need a spa, what pace they are hoping for, what they want to do and whether Switzerland factors in, how they feel about skipping the car for boats and a driver, how much they want to eat around versus dine at the hotel, when they are going, and the Como they are picturing.

A paid subscription to La Storia is $8 a month, or $80 for the year, which comes out to less than one client gift. The annual is the one I would choose.

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Now, I have been to Venice four times and I know better.

In Venice, the Logistics Are the Experience

Most cities forgive a fuzzy plan. Venice bills you for one, in hours and in euros and in the slow leak of the magic you came for. It is a place with no cars, no easy Uber, no straight line between two points, and almost everyone arrives assuming a city is a city and this one will work like the others. It does not. The water taxi they did not budget for, the bridge they did not know their suitcase would have to climb, the hotel that turned out to be on the mainland, the dinner they settled for because they were too tired to keep looking, that is where Venice trips people up, and none of it is on the list of famous sights.

Venice has been a different city every time, because Venice changes depending on who you are when you arrive. The whole job is figuring out who your client is before they get on the boat, so the city meets them as themselves.

The Series, and What You Get Every Time

This is the next installment. Every one hands you the high-impact questions for a single Italian destination, the exact ones I would ask before I booked a thing, each with a note on what the answer is telling you, all written to copy straight onto your intake form. The coast got ten. Rome got ten. Venice gets ten and a bonus, because no city hides more friction beneath the beauty, and the friction is where an advisor earns their keep.

Here is exactly what is on the other side of this:

The ten questions I would ask before I booked a night in Venice, organized to lift straight onto your intake form, each with a note on what the answer tells you.

The ten cover: what they are picturing and why Venice at all, how much luggage they are hauling, whether arriving by boat to the door matters, the bridges and the mobility of the whole group, a neighborhood feeling versus the center of it all, the water-taxi cost nobody budgets for, how much planning their food will take, whether they want a plan or want to wander, how deep their love of art and music runs, and the big sights versus a local Venice where everything is ticketed. Plus a bonus question for anyone traveling in the acqua alta months.

A paid subscription to La Storia is $8 a month, or $80 for the year, which comes out to less than one client gift. The annual is the one I would choose.

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Rome Punishes a Trip Built for No One

Most Italian destinations forgive a generic plan. Rome does not. It is vast and ancient and brutally hot in summer, and almost everyone arrives certain they already know it, the Colosseum, the Vatican, the Trevi coin over the shoulder. So it gets handed out in one shape to everyone, and it leaves people the way it left me at twenty, footsore and exhausted by the sheer volume of historical data I had just been fed in an eight-hour span.

The fix is a trip shaped to the person standing in front of you. Do I love history? Yes, but I love a charming art-filled street more. But my trip didn’t account for that.

The Series, and What You Get Every Time

This is the next installment in the series. Each article hands you ten high-impact questions for a single Italian destination, the exact ones I would ask before I planned a thing, each with a note on what the answer is telling you, all written to copy straight onto your intake form. Last week, I started with the Amalfi Coast. Rome is a different animal, a city where the friction is hidden and the assumptions run deep, which is exactly why the right questions matter more here than almost anywhere.

Here is exactly what is on the other side of this:

The ten questions I would ask before I planned a day in Rome, organized to lift straight onto your intake form, each with a short note on what the answer tells you.

The ten cover: whether they want the hustle or the hush and what kind of base fits, how much walking and heat they can handle and how to pace the days, where Rome should fall in the trip and the transport reality nobody expects, how much they want handled versus navigated on their own, whether they want experiences or tours, how early they will rise to beat the crowds, how much history and context they want, whether religious sites and the Vatican matter to them, how they want to cover the city, and whether they mean classic Roman food or modern.

A paid subscription to La Storia is $8 a month, or $80 for the year, which comes out to less than one client gift. The annual is the one I would choose.

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Some People Relax by a Pool. Some Need a Plan.

That is the thing about the coast. It can be the most restful week of someone’s life or the most restless, and the deciding factor is rarely the hotel. It is the person. One traveler unwinds on a terrace with a book and a spritz for days and never once feels stuck. Another needs a town underfoot, a boat to catch, a reason to get dressed. Both of those are wonderful trips. They are just not the same trip, and the coast will happily hand a client the wrong one if nobody asks first.

The questions that get you to the right one are not about budget or logistics. You have those handled. They are about how this particular person experiences a place, and on the coast, where the towns are so different from one another, the cost of guessing is high.

A New Series, and What You Get Every Time

This is the first of something I have wanted to build for a while. Every installment, I am handing you ten high-impact questions for one Italian destination, the exact ones I would ask before I booked a single night, each with a short note on what the answer is telling you. They are written to be copied straight onto your intake form. Lake Como, Venice, Florence, Rome, and Puglia are all coming. I am starting on the coast because it is where the gap between what a client pictures and what they book is the widest.

People also tend to lump the whole region together. Sorrento and Capri both get called the Amalfi Coast, and technically neither one is. I break down exactly what is and is not the Amalfi Coast here: What “Is” And What “Is Not” The Amalfi Coast. Because clients group them anyway, this first set covers Sorrento and the coast towns, and I am adding three bonus questions for Capri at the end.

Here is exactly what is on the other side of this:

The ten questions I would ask every Amalfi Coast client, organized so you can copy them straight onto your own intake form, each with a short note on what the answer tells you. Then three bonus questions for Capri.

The ten cover: what enjoying themselves looks like and how much structure they want, what they picture when they say Amalfi Coast, how much steep walking they can take and how flexible they are on the town, motion and seasickness, what five-star versus value means to them, what they picture when they say beach, how much the food matters, whether they want the buzz or to feel removed, how important getting in the water is and what season fits, and where the coast should fall in the larger trip.

Plus three bonus questions for Capri, and the script for the one moment you will need it, when a client brings up renting an Airbnb on the coast.

This is what every installment in the series will give you: ten questions, ready to use before your next client call.

A paid subscription to La Storia is $8 a month, or $80 for the year, which comes out to less than one client gift. The annual is the one I would choose.

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I am telling you this because that feeling is back. Your clients are reading headlines about hours-long border lines in Europe, half-hearing two different acronyms, and quietly wondering if their trip now comes with a test they might fail. It does not. But the anxiety is doing what anxiety does, and the advisor who can explain the new European border in plain language this summer is going to sound like the calmest person their clients know.

So let me break it down the way I wish someone had broken down 2021 for me. There are two systems. One is at the border right now. One has not started yet. Your clients are blending them into a single dread, and separating them is most of the cure.

The One at the Border Right Now: EES

EES stands for Entry/Exit System, and it is live today. It replaces the passport stamp with a digital record: the first time a traveler enters Europe’s Schengen area under the new system, they register at a kiosk or booth with a facial photo and fingerprints. The registration itself takes a few minutes per person. That is the entire requirement. There is no form to fill out at home, no fee, and nothing to apply for before the trip.

The lines are where the stories come from. The system finished rolling out across Europe this April, and the adjustment period has been bumpy in the way you would expect when every first-time arrival needs a few extra minutes at once. At quiet times, travelers have walked through in twenty minutes. At peak arrival banks, the big hubs have seen waits stretch to two and three hours, Italian airports included, and some countries have responded by temporarily easing the system during busy stretches while others run it in full. It is uneven, it is improving, and it is the reason your clients’ group chats are full of border horror stories this spring.

The number one question landing in my Travel Advisors Planning Italy Facebook group right now is some version of the same thing: advisors want to know how long, down to the minute, the entry and exit lines are taking. I understand the instinct, but the honest answer is that there is no number. It depends on the airport, the hour, and the day, and the professional response is to plan for it the way we planned around TSA slowdowns back home: arrive with ample time, book nothing that depends on getting through quickly, and treat a fast line as a gift rather than a guarantee. If your client breezes through in twenty minutes, wonderful, they just found an extra hour for the first espresso. If they do not, the itinerary already absorbed it.

Here is the reframe I would hand every nervous client: this is a line, not a test. Nobody is being vetted at the kiosk. They are being photographed, which their phone does to them forty times a day. The clients who suffer are not the ones who fail something. They are the ones who did not plan for the time, with a tight connection or a same-morning departure, and the planning is your job anyway. The specific timing rules I now build into every Italy itinerary, including the one about connection airports that almost nobody is talking about, are below for paid subscribers, because they have changed how I would book this summer.

The One That Has Not Started Yet: ETIAS

ETIAS is the European Travel Information and Authorisation System, and the single most important thing to know about it is that it does not exist yet. It launches in the last quarter of this year. The EU has said it plainly on the official site: no action is required from travelers at this point, and the specific start date will be announced months in advance.

When it does arrive, here is what your visa-exempt clients (Americans included) will do: fill out an online form, pay 20 euros, and in most cases receive approval within minutes. The authorization lasts three years or until the passport expires, covers multiple trips, and applies to 30 European countries. Travelers under 18 and over 70 still need it but pay nothing. The form will ask for a few things people do not expect, including parents’ first names and some background questions, which is why a heads-up from their advisor will land well. It is not a visa. It is closer to a digital permission slip, and a three-year one at that.

Now the part that makes this article urgent rather than informational. Because ETIAS has been announced but not opened, the internet is currently full of websites offering to process ETIAS applications for a fee. Every one of them is selling something that cannot be purchased. There is nothing to apply for yet. When applications do open, the only legitimate place will be the EU’s official portal, and the EU has given everyone a one-line defense that I want tattooed on every traveler’s brain: every official European Union web address ends in europa.eu. The real site is travel-europe.europa.eu. Anything else asking for your client’s passport details and credit card today is a scam wearing a flag.

One honesty note, because you know that is how I run this newsletter: I have not been through ETIAS myself. Nobody has. Which is why I spent this week in the official EU documentation and the on-the-ground reporting instead of the comment sections, and why everything above links back to sources that end in europa.eu. Requirements evolve, so the advisor’s standing habit is to verify at the official site at booking and again before departure. What I can tell you from experience is what a new requirement feels like from the gate area, and that the cure is the same now as it was on that flight to Milan: knowing, in advance, exactly what is going to happen.

The Email That Makes You the Calmest Person They Know

That is what sits behind the paywall this week, and it is the most copy-paste-ready thing I have ever put there.

The client briefing email, written for you. The exact message to send every Europe-bound client this summer, plain-language, forwardable to the in-laws, covering the kiosk, the timing, and the scam warning. Edit two brackets and hit send.

The new timing rules I build into every itinerary. The layover minimum that changed this spring, the arrival buffers for departure day, when to send the briefing relative to travel, and the connection-airport detail that determines where your client stands in their first EES line, which is the piece almost no one is briefing.

The family and group intel, plus the scam-proofing script. Who registers, who pays, who is exempt but still required, and the two sentences that will keep your clients from ever giving their passport details to a lookalike site.

A paid subscription is $8 a month or $80 for the year, and here is the part that matters this time: the day the EU announces the ETIAS launch date, paid subscribers get an alert issue with the apply-by playbook, so you will be briefing clients while everyone else is still Googling. The annual is less than the fee one scam site would have charged your client for nothing.

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The city streets of Florence do not breathe. There is no airflow unless you are near the Arno, and the stone holds the heat the way a Dutch oven holds a braise. It does not release. It just keeps going. For four days in a row that week, temperatures landed between 105 and 109. The fifth day, we drove out to Fattoria di Maiano, a working farm in the hills above the city where Senna fed donkeys and goats and could not have been happier, and the walk back up the hill almost finished me. Beautiful place. Perfect for kids. I would go back in a heartbeat. I also nearly sat down in the dirt and refused to continue.

The thing about Italian summer heat is that it is not the kind most Americans plan for. It is not dry desert heat. It is dense, stagnant, and relentless, and it catches people off guard in a way that can genuinely derail a trip, physically and emotionally. Last summer was not a fluke. European heat waves have been breaking records for several years running, and Italy in July and August is operating at a different level than it was even a decade ago.

People are going right now. Some of them are already there. And most of them were not properly briefed.

The AC Reality Nobody Puts in the Itinerary

Air conditioning in Italy does not work like air conditioning in America, and this is not a flaw in the country’s character, it is just a fundamental mismatch between expectation and reality that feels like a personal betrayal when nobody warned you first.

Four-star hotels often have AC, but it runs on a seasonal schedule that building management sets with no relationship to the actual weather. They turn it on in June. They turn it off in September. If an unusual heat wave arrives in late May or holds through October, the hotel is still on its calendar and you are on your own. Luxury properties tend to have more dependable systems, and that is one of the practical reasons, beyond the obvious ones, that a better hotel matters when summer travel is involved.

Apartments and Airbnbs are the bigger issue. AC is sometimes an add-on cost, sometimes nonexistent, and sometimes a single wall unit that moves air but does not actually cool a room below 78 degrees. Our Airbnb in Florence had AC and I was grateful for it every single day, because without it the week would have been a genuine emergency with a toddler. I got lucky. A lot of people do not research this question before they book, and they find out at 11 PM after a long day when the room simply will not cool down.

Before you confirm any July or August accommodation, ask the property directly: is the AC real, is it individually controlled, and what dates is it operational. Not “air conditioning available.” Real, working AC.

Direct Sun Is Its Own Category of Misery

The walk from the entrance of the Vatican Museums to St. Peter’s Basilica. The queue for the Colosseum at 11 AM. Any outdoor tour between 11 and 3 that spends more than twenty minutes without shade.

These are not uncomfortable. They are physical ordeals in July, and for anyone older, anyone with health concerns, or anyone who did not drink enough water that morning, they can become serious very quickly.

I keep my own rule to a maximum of three hours per outing, and in summer that is not a preference but a necessity. Heat takes it out of you in a way that is hard to predict. Someone who feels fine at 9 AM is not the same person by noon, and if the activity is still going, the misery compounds. Three hours, then rest. Not three hours then immediately another stretch of walking. Three hours, then food, shade, and a cool room.

What Goes in the Bag

Cold water is not a given in Italy. Restaurants do not automatically serve it cold, and ice is largely not how the culture operates. Carrying an insulated bottle matters. Bringing a hand fan matters. These are not silly tourist things. Everybody on a hot street in Florence is using one, Florentines included.

Most people pack for the trip they imagined, not the trip they are taking. They bring the small crossbody because it is chic. Bring a tote instead, and keep it packed. A tote fits a pashmina for church visits, a fan, a water bottle, and the small crossbody too. You cannot fit a fan and a pashmina in a crossbody, and in summer Italy you need both.

Covered knees and covered shoulders are required for entry into churches throughout Italy, for men and women both. Everyone knows this in the abstract. What they have not thought through is wearing long pants and sleeves in 107-degree heat through a two-hour morning tour and then trying to continue the day. Put church visits in the morning when it is coolest. Build a hotel break after. Go back, change into something lighter, and reset. This is logistics management that turns a miserable afternoon into a functional one.

The Lobby Bar Move

When the heat became too much in Florence and we needed to get off the street, I would walk into a five-star hotel lobby bar and order a glass of champagne or a cappuccino. Working AC, good service, a place to sit and actually recover, and a bill that was maybe 20 euros. It was one of the better decisions I made all week.

Five-star lobbies are reliably cool. The properties that operate at that level maintain their systems properly and run them regardless of the building’s calendar. The bar does not require you to be a guest. And stepping out of 107-degree stone streets into a calm, cold, well-appointed room with a drink in your hand is so restorative it almost feels medicinal. Find the good hotel near where you are touring. Know what it is before you go. Use it.

Why Lunch Deserves a Different Standard

I love Vini e Vecchi Sapori. Tommaso runs one of the best experiences in Florence, and under the right conditions I would send everyone I know there. I went that trip. I sat down with sweat already on my back and propped a fan on the table because the front of the restaurant is completely open to the street and whatever AC was running was not reaching me. It was too much. I could not enjoy it.

That afternoon changed how I think about summer days. The most authentic spots in Italy often have minimal AC because the windows are open, the kitchen is breathing heat into the room, and the whole design assumes a climate that no longer reliably exists in July. They are still wonderful. Save them for dinner, when the temperature has dropped and the streets have cooled and the open windows become an asset. Lunch belongs somewhere with working AC, full stop. It is how you stay functional for everything that comes after.

10 things I do (and tell everyone I know) to survive Italy in July.

The framework above is the honest picture of what summer in Italy feels like. Behind the paywall are the 10 specific things I actually do, and recommend to anyone traveling between June and September, to make sure the heat becomes a manageable backdrop instead of the main character of the trip. From how I book tours to what I pack to how I structure every single day, it is all in there.

If you are going to Italy this summer, or sending anyone there, this is worth having before the trip, not after. $80 for the year and the first itinerary you build with it more than covers that.

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The situations below are not horror stories meant to frighten anyone out of going. They are the specific, recurring things I have seen, experienced personally, or heard from clients directly, and the reason I give every Italy-bound traveler the same briefing before they board. Consider this that briefing.

Note that these examples aren’t all from Italy-specific situations. However, they are from tourist-heavy sites in European cities, and I’ve heard of similar scenarios throughout Italy as well.

The Petition Scam

A few years ago, I was walking the Champs-Elysées with my best friend Meredith when a group of women approached us with clipboards, asking us to sign a petition. We said no. They didn’t leave. Within about thirty seconds, there were four of them positioned on either side of us, asking questions in rapid succession, touching our arms, talking over each other. Meredith’s wallet was in a crossbody bag. She had it on correctly. She was not being careless. And by the time a bystander shouted “bad people!” and they scattered, her wallet was gone.

She got it back because the shout startled them and they dropped it. But in a crowd, on a busy day, that wallet (and her passport) was simply gone.

This is not a Paris problem or a Florence problem. It is a heavily-touristed-city problem, and Italy’s most visited spots, the Spanish Steps, Termini station, the area around the Colosseum, the Piazzale Michelangelo, the Rialto Bridge in Venice, are magnets for exactly this kind of organized distraction theft. The clipboard is a prop. The petition is a prop. The goal is to create a moment where attention is divided and a bag is accessible.

The other version involves children, usually working with an adult nearby. A child approaches with a piece of paper or a toy, seems lost or distressed, and while attention goes to the child, a second person is working from behind.

The word “no” is complete. No explanation, no apology, no engagement. Eyes forward and keep walking.

The Crossbody That Still Got Opened

I have a client who was sitting on a bench outside the Acropolis in Athens when she felt a strange pressure on her side and realized the woman who had sat down next to her had unzipped her crossbody and was working her hand inside. My client caught it. She was lucky. The woman left without a word.

A crossbody bag with a secure zipper, worn in front of the body, is still the right choice. It is just not a guarantee. Organized, patient theft is a different situation from an opportunistic grab, and it happens to prepared people wearing the right bag in the right position. The vigilance has to go alongside the bag, not instead of it.

Another non-Italy example, but you get the point!

The Taxi That Takes the Long Way

In Florence, on my first trip abroad at 20 years old, a taxi driver spent 40 minutes getting me from a pickup point to my apartment in what I later learned was a 12-minute drive. I didn’t know to ask what the fare should be. I didn’t know the route. I just watched the meter climb and felt that specific helplessness that comes from being somewhere new and not speaking the language.

Italy does not have Uber in any meaningful sense. There is a version of the app in Rome and Milan, but it functions as a luxury car service with pricing to match and availability that is often thin. Your clients lose the safety net they are used to at home: the quoted price before the ride, the route visible on their phone, the automatic payment. Official taxis use meters and the meters are legitimate. The problem is the route.

One more thing most visitors don’t know: in most Italian cities, you cannot hail a taxi from the street. You find a taxi stand near train stations, major piazzas, and airports, or you call, or you ask your hotel to arrange one. I learned this on a different trip, walking cobblestone streets with luggage and raising my arm at every passing cab, genuinely confused about why none of them were stopping. They weren’t ignoring me. That is just not how it works here.

The “Helpful” Stranger at the Train Station

When clients arrive at a major train station, particularly Naples and Rome, they may be approached by someone offering to help with their luggage. The offer feels kind. It is not. These individuals carry a bag onto the train or to the platform and then demand cash, sometimes aggressively, before releasing it…and they won’t back down. A (very) firm “no, grazie” and continuing to move is the only response needed.

The Gift That Wasn’t Free

The vendor who hands someone a flower and then explains it was a gift and then asks for money is operating on the same logic as the petition scam: create an obligation before the other person realizes what’s happening. This is most common in the evenings around major piazzas and monuments. Toys tossed toward children near tourist sites work the same way. The rule is not to accept anything from someone you didn’t approach first, particularly at night.

Street games, usually some version of find-the-ball or three-card monte, deserve a wide berth. The people appearing to win in the crowd are working with the person running the game.

Public Transit in Peak Season

Rome’s metro and Termini station are among the highest pickpocket-activity zones in the country. Crowded, rushed, confusing spaces are where distraction theft is easiest, and clients who are tired, jet-lagged, and trying to find the right platform are exactly the people who get targeted. For most travelers, a taxi or prearranged transfer is worth the cost. For families with experienced teenage travelers or clients doing extended stays who want to move like locals, transit works fine with appropriate vigilance.

The Passport Left in the Safe

In Italy, you are legally required to carry your passport or official ID when outside your accommodation. This surprises people, and it surprises them more when they are told not to leave it in the hotel safe. I admittedly don’t always abide by keeping it on me at all times, but I definitely never put it in the safe (I will absolutely forget it). If clients are stopped by carabinieri, which does happen periodically in tourist areas, they need to produce identification. A photo on a phone does not satisfy this requirement officially.

The passport travels with the client. Photocopies of the passport data page and travel insurance live separately in the hotel safe. Those copies matter more than most people realize, and the next section explains exactly why.

The Phone in the Wrong Hand at the Wrong Moment

Phone snatching from moving vehicles is a real and recurring occurrence in Naples and Rome in particular. Walking while looking at a phone, especially near roads with moped traffic, is the specific combination that makes someone a target. Phones also disappear from restaurant tables, particularly outdoor terraces, when attention is on the meal and the bag or jacket they were resting on shifts. Keep phones in a pocket or held actively, not set down in a public space.

Eight situations, all preventable, all showing up in Italy every summer without fail. The paid section is where I get into exactly how to move through Italy with confidence, including the pre-departure script I recommend advisors send every client, general guidance on bags and document security, what to look for in a travel insurance policy, and what to do if something goes wrong anyway. For $80 a year, this is the resource I wish had existed when I was 20 years old on that Florence taxi, watching a meter I didn’t know how to question. Join here.

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Yes- you read that right. I was three months into building a travel company while hand-stitching textiles for a family in exchange for a bed…in a house that was fully sustainable (read: I showered in a bucket and reused the water to flush the toilet).

However, that weekend I went to Florence for a refresher (I studied abroad there and that was from a very different lens). The farm was not a commutable distance, so I did what every reasonable, budget-conscious traveler does. I booked an Airbnb.

The listing said “private apartment in central Florence.” The photos were charming. The price was right. I was 30, fresh off a productive week of curtain-making, and felt very smart about saving money on accommodation so I could spend it on the food I had actually come to Florence for.

Here is what “private apartment” actually meant.

I arrived to a family home. To get to my “apartment,” I had to walk through the family’s living room (shoes off, please, no shoes in the house), up a staircase, into an attic. The attic had a bed. It did not have a connected bathroom. The bathroom required going back down the stairs, through the living room, and into the part of the house where the family lived. The family included a husband whose snoring I could hear through the floorboards every single night.

I was safe. I want to be clear about that. The family was lovely. The husband’s snoring was, technically, free white noise. But this was not what I had imagined when I booked, and it was definitely not what I needed for a working trip where I was nursing a wine hangover from my “research” dinner and then preparing for a brand photoshoot with Flytographer.

When it was time to leave for the train station with my luggage plus a box I needed to ship at the post office, I was hoping to ask the host if they could call a taxi.

They were non-responsive and nowhere to be found. A 5-star concierge would never.

So, I did what felt logical at the time: I rolled my suitcase out into the street, balanced the box on top of it, put a backpack on, and started waving at every cab that drove by. (You cannot hail cabs in Florence. I did not know this in 2016. I know it now.) Every cab kept driving. The box kept falling off the suitcase. I picked it up. It fell off again. I picked it up. It fell off again. I was sweating through my shirt, my luggage was now scattered across a Florence sidewalk as taxis were practically running it over, and a man at a newsstand was watching the entire performance.

I asked him, in my best apologetic Italian (“mi dispiace….”), if he would speak to the taxi company on my phone.

He did. He stayed with me on the sidewalk until the cab arrived. He helped me load the box back onto the suitcase. He said something kind in Italian that I did not fully catch but I understood completely.

I cried a little in the cab. (Of course I did.)

That night at the train station, I made a quiet vow that I have kept ever since: I will never again stay somewhere in Florence where the person I’m renting from is not actually in my corner.

The Second Time I Learned It

You would think one disaster would be enough. It was not.

A few years later, now actually running Explorateur Travel as a real company (with a real office and real clients and real laundered curtains in my own apartment), I was back in Florence on another work trip. This time I was in an Oltrarno Airbnb up one of those steep hills the city is full of. (Oltrarno is my favorite neighborhood in Florence. I would still send clients there. I will die on this hill, possibly literally.) I had booked a transfer to the airport through Blacklane, the kind of pre-paid service that exists specifically so this does not happen.

They cancelled on me. The morning of. Peak June. The same Blacklane that had cancelled on me once before.

So, I did what was apparently becoming my Florence brand: I rolled my luggage down the hill (I was near Piazzale Michelangelo), into the gelato shop on the corner of the Ponte Vecchio, and asked the gentleman behind the counter if he would call me a taxi.

He tried. Even he could not get one to come, because it was peak season and every cab in the city was already booked. I sat in his gelato shop for the better part of an hour while he made calls between customers. I bought a coffee and a bottle of water from him out of sheer guilt. He kept making calls.

A cab eventually came…and I did not miss my train to Rome, which was the first leg of three to catch my flight back to the U.S. that day.

I made another vow that day: I will never again use Blacklane. (Two cancellations is a pattern.) And I will never again assume that the cheapest version of a transfer or stay in Florence is the right one for the trip I am actually trying to take.

What These Stories Are Actually About

These are not stories about Airbnb being bad. I have stayed in Florence Airbnbs that were lovely.

These are not stories about transfer companies being unreliable. I have used transfer services in Italy that have never let me down.

These are stories about a single thing that almost nobody talks about when they’re recommending where to stay in Florence: the host. The driver. The concierge. The human who picks up the phone when something goes wrong.

In Florence, you are going to need that person. You are going to need them more than you think.

You are going to need them because:

• The restaurants you actually want to eat at do not have websites. Many do not have email. Some require your accommodation to call on your behalf in Italian.

• You cannot hail a cab on the street, and you cannot rely on Uber, and you cannot rely on every pre-paid service to actually show up.

• The historic center is a ZTL (limited traffic zone), which means driving in is illegal and the fine arrives by mail two months after you’re home.

• The air conditioning may not be on. The room may be smaller than the photos. The cobblestones may eat your stroller. The line at the famous sandwich shop may eat your afternoon.

• Mondays close half the city. Ferragosto closes the other half. Reservations open 30 days out and the best ones disappear within hours.

Every single one of those moments is the difference between a trip your client tells their friends about and a trip your client calls you angry about from a Florence sidewalk holding a box that won’t stay on her suitcase.

And the person who makes that difference is not the brand on the building. It is the host. The one who confirmed the A/C in writing before you booked. The one who made the dinner reservations because they speak the language. The one who picks up the phone at 7 AM on departure day because your transfer just cancelled.

In Florence, where you stay matters less than who is in your corner while you’re there.

The Three Tiers of Florence Accommodation

There are essentially three legitimate ways to stay in Florence, and the gap between the best version and the worst version of each one is enormous.

Tier One: Luxury hotels. This is the path of least resistance. A real concierge, a real phone line, a real human who is contractually obligated to be in your corner. The reservations get made for you. The transfers get arranged for you. The A/C is on. The Mondays are anticipated. The seven different categories of luxury hotel in Florence are all in the paid section below, matched to seven different client types.

Tier Two: Exceptionally vetted Airbnbs. Yes, this category exists. I have stayed in Florence Airbnbs that acted more like hotels than some hotels. The difference is entirely about the host. There is a specific list of questions I now require every Airbnb host to answer before I book, and that list is in the paid section. Skip those questions and you are rolling the dice on whether you end up in the attic.

Tier Three: Everything else. Hostels, the apartment over the family living room, the listing with no host bio, the transfer service with the lowest price. These are the trips where you end up bribing a gelato shop owner with a coffee while he tries to find you a taxi. I have done it. I will not do it again. I will not let your clients do it either.

What Lives in the Paid Section

If you are sending a client to Florence this year, the matchmaking is the entire job. Below is what I send my own clients and what every Italy advisor should have in their back pocket before booking another Florence stay.

Inside the paid section:

• The five questions I now ask every Airbnb host before I book a single night in Florence, including the two that have saved me from booking exact-repeats of the attic apartment

• The two transfer companies I trust in Florence and the two I have now permanently retired (one with the second-cancellation story attached)

• All seven of my personal luxury hotel picks, matched to the client type and the exact room category to book in each one (the Duomo-view splurge, the art-and-architecture lobby, the American luxury standard, the boutique sceney stay, the two out-of-center quiet retreats, the old-world villa, and the smart four-star)

• My full restaurant directory by occasion: the romantic dinners, the traditional Tuscan splurge, the casual lunches, the seasonal Tuscan order near the Duomo, the restaurant I visit every trip that nobody expects, and the no-website-no-phone relationship restaurant with the four-visit hug from the owner

• The full spectacle list: the famous Florence spots to skip by name (yes, the wine window and the TikTok sandwich shop are both on it) and the alternatives I send to instead

• The one private guide whose three-hour Overture is the only thing I let new-to-Florence clients do on Day Two

• The Chianti day-trip vineyard run by personal friends, with the booking move that turns a tasting into a Dinner in the Vines moment

If you are sending a client to Florence this year and want every recommendation in one place, upgrade to paid to unlock the full Florence directory.

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There, I said it.

For all the time I’ve spent planning, studying, and personally traveling through Italy, Milan has never been the destination I lingered in. I’ve been twice, but both visits were quick. I saw the Duomo. I admired the fashion energy. I mentally checked the “Milan” box and moved on.

And honestly? That is exactly why I wanted to have this conversation.

For this month’s La Storia audio article, I sat down with Alberto from Authenticus Italy, a DMC based in Milan, to talk about what he wishes travel advisors knew about the city. Not the Milan that gets used as a landing pad before Lake Como. Not the Milan that gets half a day before clients sprint toward Venice or Florence. The real Milan. The Milan that has quietly become one of Italy’s most interesting, international, design-forward cities.

The full audio article is where you’ll hear the complete conversation, including Alberto’s local perspective, practical planning advice, and a few gems that genuinely made me rethink how I would position Milan in an itinerary. But consider this your written companion, especially if you need the highlights before you press play.

Milan Has Changed, But Our Itinerary Habits Haven’t Always Caught Up

One of the first things Alberto pointed out is that Milan has changed dramatically over the last decade.

For many advisors, Milan still lives in the mental category of “arrival city.” Clients fly into Malpensa, maybe sleep one night, then head straight to the lakes, Venice, Tuscany, or somewhere else that feels more traditionally “Italian.” But Alberto made the case that this mindset is outdated.

Milan has become a true European capital in its own right. Infrastructure has improved significantly, including easier airport-to-city connections. International business has grown. Fashion remains central, of course, but design has become just as defining. The city has become more polished, more global, and more visually interesting, not just in how people dress, but in how spaces, hotels, restaurants, and experiences are being developed.

This is where advisors need to pause. Sometimes our itinerary habits are based on what a destination used to be, not what it has become. Milan is no longer simply the place clients land before they “start” Italy. For the right traveler, Milan can absolutely be where the trip begins.

The Last Supper Is Reason Enough to Slow Down

One of the most practical reasons to spend more time in Milan is The Last Supper.

And yes, let’s talk about the thing every advisor quietly dreads: the ticketing situation.

Alberto was very candid that securing access to The Last Supper can be difficult, even for destination partners with strong local connections. Official tickets are released roughly three months in advance, but availability is extremely limited and demand is high. His advice was not to overpromise a specific day or time too early in the planning process.

That may sound like a small thing, but for advisors, it is a major expectation-setting lesson.

Instead of telling a client, “We’ll see The Last Supper on Tuesday morning,” the better approach is to explain that access is highly sought after and that flexibility will improve the odds. If clients are staying in Milan for two nights instead of one, suddenly there is more room to work with. If they have flexibility across a couple of days, your DMC has more opportunity to source access.

This is one of those planning details that sounds logistical, but it is really about client experience. The more compressed the itinerary, the less flexibility you have. The less flexibility you have, the more likely you are to disappoint a client who assumed everything in Italy works like an open-door museum.

Spoiler: it does not.

Two Nights Should Be the New Minimum

Alberto’s recommendation was clear: if clients are going to experience Milan properly, two nights should be the minimum.

That does not mean every Italy itinerary needs Milan. But if clients are flying into Milan, asking about The Last Supper, considering the lakes, or wanting a more stylish city experience, one rushed overnight is not enough.

Two nights gives them time to arrive, adjust, experience the city at night, see the Duomo, explore Brera, visit The Last Supper if access can be secured, enjoy aperitivo, and begin to understand the rhythm of Milan.

That rhythm matters. Alberto specifically talked about “Milan by night” as one of the city’s defining experiences. Aperitivo is not just a pre-dinner drink. It is cultural. It is social. It is part of how the city moves. When clients treat Milan as a pass-through stop, they often miss the very thing that gives the city its personality.

And this is where advisors can make a smarter case for the stay. Milan is not necessarily trying to compete with Rome’s ancient drama or Florence’s Renaissance romance. It has a different energy. It is sleek, stylish, layered, artistic, and alive after dark.

The Lakes Pair Beautifully, But They Don’t Always Have to Be the Whole Stay

Of course, we had to talk about the lakes.

For many travelers, Milan is the gateway to Lake Como, Lake Garda, or Lake Maggiore. And while I will never argue against a proper lake stay with a balcony, a boat day, and a spritz situation that makes everyone question their life choices, there is also a case for using Milan as a strategic base.

Lake Como is roughly one to one and a half hours from Milan by car. Lake Garda and Lake Maggiore are farther, often closer to two or two and a half hours depending on the exact destination, but still accessible. For clients who want to see a lake but do not necessarily need several nights there, a Milan-based day trip can make a lot of sense.

This is especially true for budget-conscious clients who want the beauty of the lakes without the premium price tag of staying directly on the water.

Let’s be honest: clients love to say they want Lake Como, Venice, and the Amalfi Coast in one trip, and somehow they are always shocked when that combination is expensive. But these places are premium for a reason. Lakes, islands, and coastlines have limited space. There is only so much perimeter around a lake. There are only so many rooms with the view. Scarcity drives price, and logistics add complexity.

For some travelers, staying in Milan and visiting the lake for the day may be the smarter move. They still get the scenery, the boat moment, and the “I saw Lake Como” satisfaction, but with a more flexible city base.

That said, Alberto was also clear that the ideal version of a lake trip is still to spend at least two nights there if the client truly wants to experience it. The point is not that Milan should replace the lakes. The point is that Milan can enhance the way clients access and understand northern Italy.

The Experiences You Can’t Google Are Often the Ones That Matter Most

One of my favorite moments in the conversation was when Alberto shared an example of a special experience his team arranged on the lake: a private aperitivo at a castle after closure.

This is exactly the kind of detail that makes advisors and destination partners valuable.

A client is not necessarily going to Google “private castle aperitivo at sunset on Lake Como.” They may not even know that is a thing to ask for. But a strong DMC with local context can take a client’s vague desire for “something special” and turn it into a memorable, specific, highly personal experience.

That is the difference between booking components and designing a trip.

For advisors, this is also a reminder to ask better questions. Is the client celebrating something? Would a family member want to surprise them? Is there a proposal, anniversary, milestone birthday, or multigenerational moment that deserves more than a nice dinner reservation?

The best experiences often start with context, not a menu of options.

Milan Also Opens the Door to the Italian Riviera

Another piece of the conversation I loved was Alberto’s explanation of how naturally Milan pairs with the Italian Riviera, especially Santa Margherita and Portofino.

He described these areas almost as an extension of Milan, particularly for Milanese travelers who escape there on weekends in the warmer months. From Milan, Santa Margherita and Portofino are roughly a couple of hours away by car, making them realistic as an add-on, overnight escape, or in some cases even a long day trip.

This is where advisors can get more creative with northern Italy itineraries. Milan does not only have to lead to Lake Como. It can connect beautifully to Liguria, to the lakes, to Verona, to Venice, and beyond. Instead of building Italy itineraries that zigzag wildly from the top of the country to the middle to the bottom, advisors can use Milan as part of a smarter regional flow.

And the Italian Riviera brings its own personality. It is coastal, charming, stylish, and relaxed. Alberto talked about Santa Margherita and Portofino as places where you get atmosphere, food, seaside beauty, and that sense of stepping out of the city without abandoning the sophistication that Milan-based travelers often love.

Not Every Italian Beach Means the Same Thing

One of the more useful planning tangents in the audio article was our conversation about Italian beaches.

Because here is the thing: when a client says they want “beach,” we need to know what they actually mean.

Do they mean soft sand? Crystal-clear water? A beach club with full service? A rocky cove? A concrete platform built into a cliffside hotel? A place where they can swim? A place where they can lounge? A place that looks good in photos but may not feel like the beach experience they know from home?

These are not small distinctions.

Alberto, who is Sicilian, joked that Sicilians tend to believe only Sardinia can truly compete with them when it comes to crystalline water. But he admitted that the water along parts of the Italian Riviera, especially around areas like Paraggi near Portofino, can be surprisingly beautiful.

That context matters because Italy does not offer one uniform “beach” experience. The Adriatic side, the Tuscan coast, Sicily, Sardinia, Capri, Amalfi, Liguria, and Puglia all have different textures, water clarity, services, and logistics. Advisors who understand those differences can better match the client to the destination instead of simply matching them to a pretty photo.

Pretty photos, as we know, are often guilty of leaving out the stairs, the rocks, the transfers, the minimum spends, and the fact that “beach” may mean “chair balanced on a cliff with vibes.”

Where Alberto Would Eat in Milan

Naturally, I had to ask Alberto where he would actually eat in Milan.

For lunch, he recommended Il Salumaio di Monte Napoleone, located in the Quadrilatero near the Monte Napoleone area. It is traditional, elegant, and set in a beautiful courtyard, which makes it especially lovely in spring and summer.

For dinner, he mentioned Langosteria, which he loves for seafood. He also shared a fun fact that may surprise some travelers: Milan has one of the largest fish markets in Europe, which means seafood in the city can be excellent despite its inland location.

And for aperitivo, he pointed to Brera, specifically Fioraio Bianchi, as the kind of place where you can experience that Milanese ritual in one of the city’s most charming neighborhoods.

This is exactly why staying overnight matters. You can see the Duomo on a rushed stop. You can maybe squeeze in a museum. But you cannot understand Milan without aperitivo, dinner, and the city’s evening rhythm.

The Advisor Takeaway

The biggest takeaway from this conversation is not that every client needs Milan. They do not.

The real takeaway is that Milan deserves to be considered more intentionally.

For the fashion-focused traveler, the design lover, the client who appreciates polished cities, the traveler flying into northern Italy, the person dreaming of The Last Supper, the client pairing the lakes or the Italian Riviera, or the traveler who wants a more cosmopolitan start or finish to their trip, Milan can be a very smart recommendation.

It also gives advisors a chance to design better logistics. Instead of defaulting to one-night airport stops or sending clients immediately into expensive lake stays, we can ask whether Milan might provide a better rhythm, better access, better flexibility, or simply a more interesting beginning.

And perhaps most importantly, we can stop treating Milan like the opening credits before the “real” Italy begins.

Because Milan is real Italy. It is just wearing better shoes.

Listen to the Full Audio Article

This written summary only scratches the surface of my conversation with Alberto. In the full audio article, we go deeper into Milan’s evolution, how advisors should set expectations around The Last Supper, why the city pairs so well with the lakes and the Italian Riviera, and how local expertise can uncover the kinds of experiences clients would never know to ask for.

If Milan has been sitting in your mental itinerary as a one-night logistical stop, this episode may convince you to give it a second look. It certainly did for me.

Connect with Alberto and Authenticus Italy

Alberto is with Authenticus Italy, a DMC based in Milan that plans customized travel throughout Italy. I have a personal relationship with Alberto and his team, and I loved bringing his perspective into this conversation because Milan is not just where his company is based. It is a city he knows personally and deeply.

Travel advisors can connect with Authenticus Italy at:

Partners@AuthenticusItaly.it

Before they even arrive, they’ve usually already decided what they think it will be. Some romanticize it into something cinematic and soulful, while others count it out entirely because they’ve heard it’s dirty, chaotic, or rough around the edges.

Honestly, I think both perspectives miss the point a little bit.

Naples is not the rolling countryside of Tuscany, nor is it the polished glamour of Lake Como or the perfectly curated charm of the Amalfi Coast. It doesn’t feel manicured for tourists in the same way some other Italian destinations do, and I think that contrast catches people off guard.

But that doesn’t mean it lacks value. In many ways, I think that’s exactly where its value lies.

Naples Is for a Certain Kind of Traveler

I’ve started referring to Naples as a destination for people who enjoy what I call “gritty travel.” Not unsafe travel, and certainly not bad travel, but travel that feels a little less polished and a little more real.

The first time I arrived, my immediate reaction was that it felt chaotic, gritty, a little dirty, and very different from the Italy most travelers picture in their heads. It reminded me more of a city like New York than the dreamy version of Italy people build on Pinterest boards before a trip.

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Most people go to Italy and have a good trip. They see incredible things, eat beautifully, and come home with photos they love. And yet, they also come home tired, a little wrung out, like they need a reset after the thing that was supposed to be the reset.

I don’t think that’s because Italy is exhausting. More often, it’s because the trip was designed in a way that leaves all the friction in place. The waiting, the figuring it out, the moments where you’re already tired, and now you have to think harder. When those pieces aren’t addressed ahead of time, the experience starts to feel like something you have to manage instead of something you get to enjoy.

Over time, I’ve realized something that shifted everything for me. The fractures in a trip rarely happen in the stays themselves. They happen at the seams. The transitions. The arrivals, the departures, the in-between moments where things either flow… or they don’t.

Because of that, these have become my non-negotiables, whether I’m staying at a three-star hotel or a five-star one.

1. Book the Night Before Your Arrival

I don’t believe in arriving into Italy and hoping a room is ready. I’ve done it that way before, and it’s not the start anyone imagines when they picture stepping off a plane in Italy.

Flights tend to land early, and you arrive in that slightly disoriented state where everything feels a bit off. All you really want is to take a shower, change your clothes, and feel like yourself again. Instead, you’re often left waiting for hours with your luggage, trying to bridge the gap between arrival and check-in.

Now I always book the night before and hold the room. It isn’t about using the room overnight, it’s about having somewhere to go the moment I land. Especially now traveling with my daughter, who is three, that shift alone has made a noticeable difference in how the entire trip begins.

The only piece that matters here is communication. The hotel, villa, or apartment needs to know you’re not arriving that first night so they don’t assume you’re a no-show and release the booking.

2. Add VIP Arrival Service to Skip the Lines

I learned this one the hard way, standing in customs in Rome for over an hour while trying to make a connecting flight.

It was warm, I was dressed for the plane so I was completely overdressed, and I had that uncomfortable, jet-lagged feeling where everything feels amplified. The line barely moved, and I remember thinking how badly I just wanted to get through, change, and move on with the day. I ended up barely making the connection, and it was one of those moments that stays with you.

That experience completely shifted how I approach arrivals.

Now, when it makes sense, I add VIP arrival services. Someone meets you, walks you through the process, and removes the need to stand in line when you’re already at your limit. It’s not about excess, it’s about protecting your energy at the exact moment it’s most depleted.

When we landed in Venice, we used this service, and the difference was immediate. We didn’t have to navigate the airport on our own or walk the full distance to the dock. We were guided straight to our water taxi and into the hotel, landing around 9:00 and in our room by 10:00.

At the time, my daughter was two, and having the room ready made all the difference. She had a pack-and-play already set up, she was able to nap, and we were out for a relaxed lunch shortly after. The entire day unfolded easily, and that first day set the tone for everything that followed.

3. Arrange a Private Transfer for Arrival Day

Even if I simplify nothing else, I simplify this.

Arrival day is not the time to navigate a new train system, decipher signage, or move through multiple steps to get where you’re going. That can absolutely be part of the trip later, but in that first moment, it adds unnecessary pressure.

A private transfer removes the need to think through what comes next. You’re met, guided, and taken exactly where you need to be without having to problem-solve while jet lag is setting in. It’s a small decision that creates a much smoother start.

4. Start in a Destination That Lets You Ease In

I rarely begin a trip in a destination that requires immediate structure.

Instead, I prefer to start somewhere that allows me to ease into the experience. A place where I don’t need to be anywhere at a specific time the moment I arrive. That might look like the countryside, a coastal town, or anywhere that naturally invites a slower pace.

There’s something about waking up that first morning, still adjusting, and not having a schedule waiting for you. Sitting outside with a coffee, letting the day unfold without rushing into a tour or trying to absorb information before your body has caught up.

I avoid booking anything that first afternoon or early the next morning, and that flexibility makes a noticeable difference in how the trip feels.

5. Book First-Class Train Tickets (With Lounge Access)

If I’m taking trains in Italy, I book first class every time, and I specifically look for tickets that include lounge access.

Part of this is comfort. You have assigned seats, more space for luggage, and you’re not lifting bags overhead or navigating crowded aisles. But the lounge access is what really changes the flow of the day.

Instead of standing on a platform with your luggage, watching for your train and waiting in the crowd, you have a calm, comfortable place to sit beforehand. It creates a buffer between destinations that feels intentional instead of rushed.

There’s also a different energy in first-class cars themselves. There’s service, carts moving through, and an overall feeling that aligns more with a vacation than a trip.

On our train from Venice to Rome, we booked a private enclosed cabin. At the time, I was traveling with my two-year-old, and that setup changed everything. She had space to move, we weren’t worried about disrupting anyone else, and the entire experience felt contained and manageable instead of stressful.

There’s also a sense of ease I personally feel in those cars. Whether that’s perception or reality, it contributes to the overall experience, and that’s what I’m optimizing for.

6. Add VIP Assistance at Train Stations

Train stations in Italy have a very specific energy to them.

The train pulls in, people are moving quickly, you’re checking carriage numbers, and all of a sudden what should be simple starts to feel rushed. Add luggage into the mix, and it can quickly become overwhelming.

This is where I like to add VIP assistance.

Having someone meet you, guide you to the correct carriage, and physically help with your luggage removes that moment of chaos entirely. You’re not rushing, you’re not second-guessing, and you’re not trying to manage everything at once.

It creates a much smoother transition from one destination to the next and eliminates that frantic feeling that can happen in those moments.

7. Pre-Plan Your Tipping in Advance

One of the easiest ways to reduce mental load while traveling is to remove small decisions ahead of time.

Tipping is one of those details that seems simple, but in the moment, it turns into a series of questions. How much should we give, do we have the right amount of cash, are we doing this correctly?

Before I leave, I take an hour to map it out. I decide what I’ll tip each driver and guide, and I prepare envelopes with euros already inside, labeled and ready to go.

When the moment comes, I don’t have to think about it. I simply hand it off and move on, which keeps the experience smooth and allows me to stay present.

8. Turn Every Logistical Leg Into Part of the Experience

This is one of my favorite ways to elevate a trip, and it’s often the most overlooked.

Long drives, transfers, anything that feels like a “get from point A to point B” moment, those are opportunities.

Instead of treating them like something to get through, I like to build something into them.

One of my favorite examples of this was a trip with close friends. We were driving from Rome out to the countryside and instead of going straight through, we stopped for a long, relaxed wine lunch at Madonna del Latte.

It broke up the drive, gave us a chance to stretch our legs, and honestly set the tone for the entire trip. We weren’t rushing to get somewhere, we were already in it.

That shift changes how the day feels.

9. Confirm Your Needs with the Hotel in Advance

This is one of the simplest things you can do, and it makes a surprising difference.

About two weeks before arrival, I’ll reach out to the hotel directly and confirm any specific needs. Things like a pack-and-play, room configuration, or anything that would make the stay more comfortable.

They likely already have this information from the booking, but that extra touchpoint ensures nothing gets missed and removes the need to think about it later.

10. Use the Concierge Before You Arrive

People often wait until they’re on the ground to engage with a concierge, but I prefer to reach out in advance.

Even at smaller hotels, you can often get thoughtful recommendations or assistance with reservations. And at larger properties, they can take quite a bit off your plate before you ever arrive.

It’s a simple way to reduce decision-making during the trip itself.

A Note on Restaurant Reservations

If you’ve read anything I’ve written before, you already know this.

I don’t even consider it a tip anymore, it’s just a given. You should always have restaurant reservations.

NOTE: You can always cancel them, and you should if your plans change.

That’s simply the polite thing to do. But wandering, especially with a family, trying to find somewhere to land at the end of the day is one of the fastest ways to introduce stress into an otherwise beautiful experience.

It’s another one of those seams where things can either flow… or not.

The Difference Between a Trip and a Vacation

None of these decisions are dramatic on their own, but together they remove the friction that quietly builds throughout a trip.

The waiting, the second-guessing, the transitions that feel clunky instead of seamless, all of it adds up. When those pieces are removed, the experience shifts.

A trip asks something of you the entire time, while a vacation gives something back. Italy has the ability to be the latter, but it requires a bit more intention on the front end.

Want to Plan Italy This Way?

If this is the kind of experience you want to create, this is exactly what I teach inside my 5-lesson Italy planning course.

It’s not just about where to go. It’s about how to think through the flow of a trip, how to time it properly, and how to make decisions that allow the entire experience to feel seamless from start to finish.

The course is currently on sale HERE through May 15 if you want to take a deeper dive.

There are certain conversations that just hit differently when you hear them. The nuance, the tone, the way someone pauses before they say something real. Writing can’t always capture that.

So, first official audio installment of La Storia. And I couldn’t think of a better person to kick it off than Laura Massoni of See Italy Travel, represented by All About Rep, owned by Yina Munoz.

I met Laura at ILTM Cannes. Within about five minutes I knew she was someone worth talking to. Not a surface-level “Italy is magical” conversation. A how do we actually plan this well conversation.

You can listen to the full thing here.

Italy Isn’t Hard… Until It Is

Italy tricks people.

On paper, it feels familiar. You’ve heard of the places. You’ve seen the photos. You think you get it.

And then you’re standing in a train station with luggage, a platform number that keeps changing, and the slowly dawning realization that there were about 47 decisions you didn’t know you needed to make.

Laura said something in this conversation that stuck with me: the product isn’t the itinerary. It’s the people.

Simple. Not always practiced.

On Luxury

This is where I think the travel industry gets it wrong most often.

Luxury isn’t five stars and a beautiful lobby. It’s how you feel when you walk in the door. It’s the difference between being handed a key and actually being welcomed. The hotel that remembers your name versus the one that just scans your passport and points you to the elevator.

Sometimes the most memorable version of that isn’t a branded property at all. It’s a villa. An agriturismo. Somewhere small that genuinely gives a damn that you’re there.

I will take that every time.

The Part Nobody Plans For

The unsexy truth: the thing that makes or breaks an Italy trip is usually not the Colosseum.

It’s the train station. The transfer. The moment things stop feeling seamless, quietly, and then all at once.

That’s where the right support changes everything. Not glamorous. Not the thing anyone puts on the highlight reel. But it matters more than almost anything else.

On Seasonality

Italy is not as “open” as people assume.

Things close. Regions shift. A place that’s electric in May can feel completely different in August. This isn’t a reason not to go. It’s a reason to actually think about where you’re going and when.

There’s always a version of Italy that works. You just have to know where to find it.

Why I Wanted to Have This Conversation

The real takeaway isn’t “hire a DMC” or “book earlier.”

It’s that you don’t know what you don’t know. And Italy is not the destination to wing it, not if you actually care about the experience.

The best trips I’ve planned, and the best ones I’ve been on, always have someone on the ground who understands the nuance you cannot Google.

That’s the difference between a trip that looks good on paper and one that actually feels incredible when you’re in it.

Italy isn’t meant to be rushed. It’s not meant to be guessed at.

It’s meant to be done well.

And when it is, there’s nothing like it.

Let’s talk about Mondays.

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