Here are a handful that may surprise you and, honestly, shocked me after our trips there…

Turks & Caicos

This one had long been on my dream list, as I remember in my 20s a couple telling me about how they had honeymooned there and that it was the most stunning place they’d ever seen. I made a note that someday I would get there to see this most “stunning place.”

Indeed Turks & Caicos’ pale blue Caribbean water is unparalleled, but that’s about as far as it goes, unfortunately. Like many Caribbean islands, the interior is like a desert and nothing to see.

But that’s not the worst of it. For me it was three-fold: safety, expense and unfriendly people.

As I was trying to book our accommodations, I happened upon many horror stories of people’s vacation rentals being broken into, especially at night while they were sleeping. The thieves would take whatever valuables were not in their bedrooms. Often violence ensued in parts of the island, as well, with cases of people being killed on the main stretch of beach on Providenciales.

The tourism bureau even advises in its tourism magazine to leave the windows rolled down in your car rental because otherwise they will be broken by individuals looking to see what’s inside. I mean it’s bad when you have to put that in your tourism magazine advertising your destination!

While we did end up in a gorgeous vacation rental (Lighthouse Cottage at Sailaway Cottage), that is one of my favorite vacation rentals ever, they had safes in all areas of the rental, and we always put our valuables in these at night and when we left. And I was essentially unnerved the entire time.

Another gripe of mine: Everything is outrageously expensive! We went to the local grocery to load up on some things we could make in the vacation rental only to see we would spend 4x what it would cost at home. Absolutely outrageous and no wonder the people who live here are not happy people.

My final reason I’d steer clear of Turks & Caicos is that most people there were not just unfriendly, they were downright rude. Contrast this with the Dominican Republic, which (aside from London) had the friendliest people I’ve ever encountered in the world.

Check out my Families Fly Free podcast episode all about Turks & Caicos to hear more.

Subscribe now

La Fortuna, Costa Rica

Another shocker is La Fortuna, Costa Rica, home of the Arenal Volcano. This was another destination that we’d wanted to go to for a long time that took us 8 years into our flying free journey to get to. I’m glad I went, but it was very disappointing and I’d never return. Costa Rica - check!

The wildlife, the monkeys, the rainforests, the volcanoes. I’ve heard so many wonderful things about Costa Rica from so many people, and I absolutely couldn’t wait to see it myself. While I did enjoy one portion of the country (or rather, one specific resort I should say), the remaining portions we saw - La Fortuna and San Jose - left a lot to be desired.

What I DID love was the Hyatt Andaz Peninsula Papagayo on the northwest coast of Costa Rica. We score a heckuva deal in points for this, paying just 80,000 points for 3 nights at this beautiful resort with monkeys in the trees right outside your window (priceless). If we had paid cash, it would have cost us $6,600! This remains my best points redemption to date.

Check out my podcast episode on Costa Rica where I explain how I saved $10,000 on travel expenses using miles and points.

The Peninsula Papagayo is also just a short 2 1/2 hour flight from Houston, making it a great alternative to Mexico or the Caribbean for a beachfront getaway (with monkeys to boot!). We did make the effort to drive outside the Peninsula to see what else we could find, only to discover there was nothing else to worth seeing in the area.

After we spent 3 nights at this resort, we drove to La Fortuna. That was a pretty drive, especially around Lake Arenal, with interesting creatures crossing the roads and lots of birds to see. In hindsight, if you’re going to La Fortuna, I’d advise staying in this area and OUT of the city of La Fortuna.

La Fortuna, home of the Arenal volcano (which, itself, was amazing to see and can be seen anywhere in the town), is one giant tourist trap. Super disappointing. I’d seen the quaint shot of the town shown above and thought it looked absolutely darling. Darling it is not. You can shoot that photo and cut out all the ugly tourist horrificness that is literally surrounding it on all sides and make it perfect for social media. But it is not a true photo of what the area looks like.

As you get closer to La Fortuna, you are bombarded with billboards at every turn promoting all the different touristy rainforest things you can do there. I was so looking forward to hiking and see nature in this area and you literally cannot hike ANYWHERE without paying a fee for access. Many of the “hikes” are manufactured walks on a path where there is not much to see.

And don’t think you are going to see a sloth while you are there because you are not. No one mentions that sloths are next to impossible to spot! They are VERY high up in the trees and blend right in. Guess what? You’re going to have to pay for a guide to show you where the sloths are.

We did have a fairly nice vacation rental here with views of the volcano (but you can literally see the volcano from ANYWHERE in La Fortuna) that was super cheap ($495 for 3 nights, which I erased with my Capital One Venture X miles), but I also did not feel safe here.

It was a ways from the town, down a dirt road, and one evening at 10pm all the power went out. I’m sure part of the issue is my paranoia but, not knowing the area, I felt like it was a prime opportunity for someone to rob us. They didn’t. And it was a normal power outage that regularly happens in the area.

Another safety issue no one tells you about… there are men in neon crosswalk vests who charge you to park in public parking spots on the street. Each man has “his” parking spots and they imply threats if you don’t pay them. Basically like the mafia of Costa Rica. Fun. This happened in both La Fortuna and in the Peninsula Papagayo area.

The whole area has been utterly commercialized and is in no way “natural” anymore. Steer clear is my advice and find some other areas of the country that are more untouched.

One last comment on San Jose. This is the country’s capital city that you will likely fly into and out of. It is awful. Costa Rica is not a third world country, but visiting this city it sure feels like it. Be prepared for crazy driving and feeling unsafe.

Maybe you loved these places :), but I did not.

What popular places have you traveled to that you would never return to? Please share!

Leave a comment

It may sound cool to have status with an airline, but unless you’re flying frequently for your job and your job is paying for it, I’m not a fan. At least, not if you’re trying to save money on travel.

And Southwest’s status is one of the worst when it come to any value you get by holding it.

Southwest’s elite “status” (by this I mean A-List and A-List Preferred, not Companion Pass, which is technically a “status”) used to have a handful benefits that were handy; however, those went by the wayside with all of Southwest’s recent changes.

Now, there is no reason whatsoever to try and earn status with Southwest.

One of the best perks used to be the fact you were checked in ahead of everyone except for those who paid for their highest fare. That usually meant you scored a boarding order in the A15-30 range, which was super helpful for scoring a better seat.

Now, if you know what you’re doing (you just need to hold the right Southwest card), you get a free seat assignment with every booking, so all that is for nought.

Another GREAT perk was Same-Day Change. With Same Day Change, at midnight, the day of your flight, you can move yourself to ANY other flight that day (before or after your currently booked flight) so long as there’s availability.

But they took that perk away from elite status! Now, you can get it simply by booking a Choice fare instead of a Basic fare.

The only things you get with Southwest status these days are things you can easily earn for A LOT LESS (or free!) by holding one Southwest card or booking a Choice (the 2nd least expensive) fare.

Why Southwest Wants You to Earn Status

Here’s the real reason Southwest wants you to earn status…

It’s not because they want to reward you for being a loyal customer, though, I suppose, that doesn’t hurt, but honestly, they’re not giving you much for being a loyal customer…

The No. 1 reason they want you to earn status is because you spend a TON of money with them to earn it.

You either:

1. Fly a gazillion paid flights (By gazillion, I mean 20 paid flights to reach A-List and 40 to reach A-List Preferred; that is A LOT people!) - I NEVER RECOMMEND PAYING FOR A CASH FLIGHT ON SOUTHWEST unless your employer is paying for it for you. You should always book Southwest in points only, not only because points are free but because they are flexible, never expire and allow you to keep reducing the points cost when the price goes down after you’ve booked.

2. OR spend a gazillion on their credit cards (By gazillion I mean $70,000 on Southwest Priority to reach A-List or $140,000 to reach A-List Preferred) - You should NEVER put the majority of your spending on ANY airline card because you can earn more points and flexible points that can be used in many ways elsewhere!

Neither of these things is good for you. It’s good for them.

You can literally get 99% of the benefits of status by paying $229 a year in annual fees to hold a Southwest card and by booking Choice instead of Basic, which is likely to cost you a couple thousand more points.

What You Get With Southwest Status & How You Can Get Those Benefits Elsewhere

Here’s what you get with Southwest status these days and how you can get that benefit elsewhere:

A-List

• Select a Preferred or Standard seat at the time of booking - Available by holding the Southwest Priority ($229 annual fee only vs $70,000+ spent on a Southwest card) or Southwest Performance Business cards.

• Board in Group 1 - This is truly an exclusive perk, but who cares anymore when you now have an assigned seat on Southwest? You do get earlier bin access for a checked bag, but why not just check your bag now, because that’s ALSO free with ANY Southwest card. Way easier than fighting for bin space with all the people who don’t understand how to still get a free checked bag!

• 1 checked bag free - Also a perk of holding ANY Southwest card (for you and up to 8 people, including your Companion, on your reservation)

• 25% earning bonus - You should never be paying for flights on Southwest! Always use points to book Southwest.

• Same-Day Standby - You also get this by booking a Choice fare, but Choice also gives you Same-Day Change, which is WAY better. It confirms your seat without you having to go to the airport. Same-Day Standby is only for flights EARLIER than your scheduled flight and you have to go to the airport to confirm. And you might not even get on the flight…

• Priority Lane & Express Lane - Another exclusive perk, but again, who cares? I think this is really only helpful if you regularly encounter outrageous lines at your airport to check a bag with Southwest.

• Priority Phone Support - My Families Fly Free members have an insider # I share with them that gets better service than the A-List #.

A-List Preferred

All of the above plus:

• Up to 2 premium drinks - Um, this saves you $14 - hardly worth spending $140,000 on your Southwest card!

• 2 free checked bags - More than 1 checked bag per person is rarely, if ever, needed. Just have anyone else flying with you (even kids) check a bag, which they get free by anyone on your reservation holding a Southwest card.

• Extra Legroom Seating at time of booking - You can book a higher fare type to get this or hold Southwest Priority or Performance Business. With those cards, 48 hours ahead of your flight, you can move yourself into the Extra Legroom Seats FREE! I’ve never had any problem with this, as most people don’t realize it’s a perk of those cards.

• 100% earning bonus - Again, doesn’t matter when you should be always booking Southwest in points.

So skip earning status, and instead:

• Put your everyday spending on a flexible travel rewards card instead of on a Southwest card

• Use Southwest points to book your flights FREE instead of paying cash

• Hold Southwest Priority to get your free seats and checked bag

• Book Choice or a higher fare type if you want access to Same-Day Change

Much smarter! Don’t fall prey to their desire for you to spend, spend, spend on their cards.

Did you learn anything new? Please share in the comments!

There is a huge new bonus ending Monday, June 15, 2026 at 9am EST for the Chase Sapphire Reserve card, and it is the highest bonus I have ever seen not just for this card, but the highest EVER for my favorite flexible points system: Chase Ultimate Rewards.

The current bonus is 150,000 Chase Ultimate Rewards points after spending $6,000 in the first 3 months.

That is a LOT of free travel.

At a minimum, that bonus is worth at least $1,560 in free travel. But used strategically, it can be worth much more.

If you came here from my email and decide this card makes sense for you, please go back to that email and use the application link there. If you would like access to that email, please comment below or send me a message with your email address.

It helps support my small business and allows me to keep sharing practical travel rewards tips like this. I really appreciate it!

For example, 150,000 Chase points could be worth up to $9,000 when transferred to Hyatt to book an all-inclusive resort or $2,300+ when transferred to Southwest and used to book free flights.

And if you have a Southwest Companion Pass?

That can effectively double the value $4,600+, because one person can fly with you for NO dollars and NO points, just the taxes and fees, for as long as you have the pass. And my system teaches you to ALWAYS have a Southwest Companion Pass.

This is why Chase Ultimate Rewards have long been my favorite flexible points system. They accomplish all the free travel you want to do within ONE points system.

No need to have points in every travel loyalty program. Earn your Chase points and then move them where you need them or use them to book ANY hotel or ANY airline. I explain how below…

Why I Love Chase Ultimate Rewards

There are a lot of people online who will talk about luxury perks, airport lounges, first-class flights and fancy hotel redemptions.

That’s all fine.

But that’s not why I love Chase points.

I love Chase Ultimate Rewards because they transfer to the programs I think are most useful for families who want to travel more without spending thousands of dollars: Southwest and Hyatt.

Southwest is, hands down, the best airline for getting the most free flights, especially for families. And, YES, even with all of their recent changes!

Hyatt is the best hotel chain for free stays, because you can pay WAY fewer points for a Hyatt stay than you would pay with Marriott, Hilton or IHG.

Don’t want to fly Southwest or can’t stay at a Hyatt? Not to worry!

Use the Chase Travel Portal to book other airlines and hotels with your Chase points. No transfer needed!

Insider Tip: It’s almost always cheaper to book Marriott or IHG with points within the Chase Travel Portal than it is to transfer them to Marriott or IHG and book directly; always compare the two points prices and choose the cheapest option!

Even better, you can book DIRECTLY with ANY hotel or airline or charge ANYTHING to the card and use your points (valued at 1 cent each) to “pay for” the charge within 90 days using Chase Pay Yourself Back. That covers things you can’t normally book with points like:

• Airbnbs/vacation rentals

• Cruises

• Disney park tickets

• Tours

• Dining

• ANYTHING

That combination of options is one of the things that makes Chase points so powerful.

You are not locked into one airline.

You are not locked into one hotel chain.

You have options.

And when you use those options well, Chase points can stretch a very long way.

If you came here from my email and decide this card makes sense for you, please go back to that email and use the application link there. If you would like access to that email, please comment below or send me a message with your email address.

It helps support my small business and allows me to keep sharing practical travel rewards tips like this. I really appreciate it!

My Favorite Ways to Use Chase Points

Here are the ways I think Chase points are most valuable.

1. Transfer them to Hyatt

This is where you will get the highest value out of your points hands down.

I once transferred Chase points to Hyatt to book the Andaz Peninsula Papagayo in Costa Rica for 29,000 points/night for 3 nights, saving us more than $8,000!!

Hyatt award nights can require far fewer points than other hotel programs, which means your points can go much further.

2. Transfer them to Southwest

Southwest is THE BEST way for families to always be able to fly for free.

The points are easy to use, there are no blackout dates, and Southwest makes it simple to cancel and rebook if your plans change.

Plus, there are a lot of ways to work the points price down once you’ve booked if you know the ins and outs of the Southwest system.

And when you pair Southwest points with a Companion Pass, the value DOUBLES.

If one person in your family has a Companion Pass, one person can fly with them for no dollars and no points on every Southwest flight they take together, aside from taxes and fees ($5.60 per way).

My system teaches you to ALWAYS have a Southwest Companion Pass, so that person ALWAYS flies for free. There’s no better savings than that!

That is where the math can get really exciting.

3. Use them for other travel through Chase Travel

Use Chase points to book flights, hotels and car rentals through the Chase Travel portal. You’ll get a minimum of 1 cent of value and up to 2 cents through the Chase Sapphire Reserve “points boost” system.

This gives you flexibility when Hyatt or Southwest are not the right fit.

4. Use them to “pay yourself back” for charges

This is one of the most overlooked benefits, and it is SO helpful to understand (and so easy to do ;-)).

With this card, you can charge eligible purchases to the card and then use your points to cover those charges within 90 days at a value of 1 cent per point.

It’s called Chase Pay Yourself Back.

Select the charge and then use your points to pay for it the charge, so you no longer owe it.

It lets you cover ANY charge versus Capital One Venture, which only allows you to use your points to cover “travel” charges. This gives you ultimate flexibility.

If you came here from my email and decide this card makes sense for you, please go back to that email and use the application link there. If you would like access to that email, please comment below or send me a message with your email address.

It helps support my small business and allows me to keep sharing practical travel rewards tips like this. I really appreciate it!

But Let’s Talk About the Annual Fee

The Chase Sapphire Reserve now comes with a $795 annual fee.

That’s pretty hefty.

You need to consider whether you can offset, or almost offset, that annual fee with benefits you will actually use.

The easiest one is the $300 annual travel credit.

This is one of the simplest travel credits out there. You charge eligible travel purchases to the card, and Chase credits you back for the first $300 each account anniversary year.

That brings the annual fee down quite a bit.

The card also includes:

Up to $300 in StubHub credits each year
You get up to $150 from January through June and up to $150 from July through December. If your family attends sporting events or concerts, this could be useful. We attend LOTS of sporting events, concerts and love to see comedians so this one is easy for us to offset another $300.

Airport lounge access
This includes Chase Sapphire Lounges, which are phenomenal, plus 1,300+ Priority Pass lounges around the world plus the ability to bring 2 people in with you. Some of my Families Fly Free members (a private membership that is no longer open to new members) are using lounges not just for the experience, but to save money on airport food by eating in the lounge before flights. That, too, can help offset the annual fee, as airport food for 3 people is NOT cheap.

Global Entry, TSA PreCheck or NEXUS credit
You can receive up to $120 every 4 years. My family has always used credits like this from travel cards to get and renew TSA PreCheck.

So if you need to get a TSA PreCheck or it’s time to renew, take another $70-$85 off the annual fee.

Apple TV+ and Apple Music
If you already pay for one of these subscriptions, this can also be a savings.

The Edit hotel credits and perks
The card includes up to $500 annually for prepaid bookings through The Edit, split into two $250 credits. These stays can also include benefits such as daily breakfast for 2, property credits and potential room upgrades.

Insider Tip: One of my Families Fly Free members is using Hyatt hotels that are part of The Edit collection in a way that also helps her accrue nights toward Hyatt elite status, which ultimately saves her family even more money.

Up to $250 in statement credits through 12/31/26 on select prepaid Chase Travel hotel bookings
This applies to qualifying stays with brands including IHG Hotels & Resorts, Montage, Pendry, Omni, Virgin Hotels, Minor Hotels and Pan Pacific Hotels and Resorts.

Complimentary IHG One Rewards Platinum Elite Status
This is not why I would get the card, but it can be helpful if you ever have an IHG stay! My members love the Kimpton Seafire on Grand Cayman, for example.

DashPass membership
The card includes a complimentary DashPass membership. If you have kids, there’s a good chance they love DoorDash, and this can be a savings.

There are more benefits too, but those are the ones I would consider first when deciding whether the annual fee makes sense.

The Earning Rates

The card also earns:

• 4x points on flights booked directly

• 4x points on hotels booked directly

• 3x points on dining

Travel Protections Matter Too

Another big perk of the Sapphire Reserve is that it comes with great travel protections, including:

• Primary rental car coverage

• Trip cancellation and interruption insurance

• Trip delay reimbursement

• Lost luggage reimbursement

• Baggage delay insurance

• Emergency evacuation and transportation

• Emergency medical and dental coverage

These are not comprehensive, and I recommend you get actual travel insurance if you are traveling abroad or have concerns, but they sure don’t hurt ;-)!

One Important Chase Rule

This card does count as one card under Chase’s 5/24 rule.

That means if you have opened 5 or more personal credit cards across all banks in the past 24 months, you may not be approved. Note: Chase, Citi and AMEX business cards do NOT count as part of the Chase 5/24 rule.

Before you apply, make sure this card fits into your overall card strategy.

My Bottom Line

This is definitely a card to consider for this HIGHEST-EVER bonus, ending Monday, June 15 at 9am ET. It has great perks, and the bonus is worth tons of free travel for your family. Just make sure you’re comfortable largely offsetting the annual fee.

If you came here from my email and decide this card makes sense for you, please go back to that email and use the application link there. If you would like access to that email, please comment below or send me a message with your email address.

It helps support my small business and allows me to keep sharing practical travel rewards tips like this. I really appreciate it!

Again, only apply if this card makes sense for you, if you can meet the minimum spend responsibly, and if you can make the annual fee work.

But for the right person, this 150K Chase Sapphire Reserve offer is one of the strongest flexible points offers I’ve seen.

Most people who collect points never actually use them well. And it’s not because they don’t have enough.

It’s because they’re overwhelmed with all of the different options.

After years of doing this (and helping thousands of families do the same), I’ve found something surprising:

The people who travel the most for less aren’t doing more…

They’re doing less.

• They’re not juggling 10 credit cards.

• They’re not chasing every single credit.

• They’re not trying to learn and collect points in every airline and hotel program.

Instead, they follow a much simpler approach.

Here’s what that looks like:

• Focus on one primary airline and one primary hotel chain

• Use one flexible points card for your everyday spending instead of trying to collect points in a bunch of different places

• Narrow your strategy instead of expanding it

• Stop applying for too many cards! I can’t stress this enough. You really only need 2-4 cards to ALWAYS fly your whole family for free AND get some free hotel stays, too

• Learn how to pay fewer points than what you see advertised

This is the exact approach I’ve used to consistently travel for a fraction of the usual cost — often for just 5,000–10,000 points per person per roundtrip flight.

But here’s the problem:

Most blogs, podcasts and websites give you too much information…

Not a clear, simple plan.

So you end up with points — but no real strategy for using them.

You end up with overwhelm, instead.

If that’s you, start here:

I put together a short free guide that walks through the 5 key ways to simplify your travel rewards strategy and actually start using your points.

You can get my “5 Ways to Simplify Your Travel Rewards Strategy” guide by clicking below.

Get the Guide

This guide is quick, practical and designed to cut through all the noise.

If you’ve ever felt like:

• “I have points, but I’m not using them well”

• “This feels way more complicated than it should be”

• “I don’t have time to figure all of this out”

…this will help you get unstuck.

You don’t need more strategies.

You just need a simpler way to use the ones that actually work!

Download my free “5 Ways to Simplify Your Travel Rewards Strategy” guide below:

Get the Guide

In this episode, Bret shares:

• Booking 10-13 free trips annually (New Orleans, Los Cabos, Palm Springs, Hawaii and more!)

• Leveraging Hyatt points for stays in prime locations

• Planning a dream family Hawaii trip for his adult kids – paying for everyone's flights with points

• His strategy for booking multiple options, then choosing what works best for his wife's teacher schedule

About Families Fly Free: Ready to stop waiting and start traveling? Families Fly Free teaches families a simple system to fly for free using travel rewards. Join our community at FamiliesFlyFree.com.

• The major mistakes people make (including that Chase transfer trap)

• Why "bonus points" don't always mean what you think

• The smartest, simplest path to earning the Pass—without cobbling together points from a dozen different places

• How to have a Southwest Companion Pass for nearly 2 full years (yes, really)

If you've been piecing together your Companion Pass strategy through Google searches and forum posts, this episode will save you from costly mistakes and wasted time.

Ready to master the full system? Join Families Fly Free to get the complete roadmap, perfect timing strategies and step-by-step personalized guidance so you never miss out on this valuable perk: https://www.familiesflyfree.com/join

Got questions about Families Fly Free? Text me at 844-403-2263.

Music Credit:

Inspiring Optimistic Upbeat Energetic Guitar Rhythm by Free Music | https://soundcloud.com/fm_freemusic

Music promoted by https://www.free-stock-music.com

Creative Commons Attribution 3.0 Unported License

https://creativecommons.org/licenses/by/3.0/deed.en_US

What you'll learn:

• Why constantly opening new cards needs to stop (especially with Chase's new restrictions)

• To pay attention to the cards that earn you the most points in every category

• To stop wasting your spending on airline cards

• How to stop paying the listed points price for both flights and hotels

• The uncomfortable truth about lounge access for families in 2026

• How to simplify your approach while still meeting all your free travel goals

✨ Learn my simple, step-by-step Fly Free Formula™ for how to maximize your miles to always fly your whole family free and beyond with personal support, a customized plan and live content, along with travel inspiration in my Families Fly Free membership:

👉 Join: https://www.familiesflyfree.com/join

Got questions about Families Fly Free? Text me at 844-403-2263.

Music Credit:

Inspiring Optimistic Upbeat Energetic Guitar Rhythm by Free Music | https://soundcloud.com/fm_freemusic

Music promoted by https://www.free-stock-music.com

Creative Commons Attribution 3.0 Unported License

https://creativecommons.org/licenses/by/3.0/deed.en_US

Here's what you'll learn:

• How breaking Southwest flights into segments can save you thousands of points

• The incredible Hyatt Andaz redemption that delivered 7 cents per point in value—my best points redemption ever

• How to use Capital One or Chase points to cover vacation rentals and other expenses

• Real numbers of points paid and cash saved

• Critical car rental warnings for Costa Rica that could save you hundreds and major headaches

If Costa Rica is on your bucket list or you want to see exactly how to maximize multiple points currencies for a trip step by step, this episode breaks it all down.

Bottom line: $10,000+ saved for an unforgettable family adventure!

You'll learn:

• Why earning your pass in December 2025 vs. January 2026 costs you a whole year of benefits

• Quick ways to finish earning the remaining points before year-end (if that makes sense for you)

• How to pivot your strategy to card combinations for 2026-2027

• Why this mistake isn't the end of the world—just a detour to Plan B

If you've been stressing about your Companion Pass timing, take a deep breath. I've got you covered!

• Earn airline AND flexible points inside shopping portals

• How to earn points IN store

• How to stack points-earning

• How to get EXTRA discounts on top of earning points

• How to earn points at Amazon and Target

Use all the points you earn for your family's free travels in 2026! Happy shopping!

Ready to stop wasting points and perks and make travel rewards EASY? Join Families Fly Free, my popular travel membership where I teach you my Fly Free Formula and show you a simple system to fly your whole family for free for life with the support you need for success. Stop doing it alone and join hundreds of families just like you who've saved $6 million+. Learn more at FamiliesFlyFree.com/Join.

I'll walk you through how to decide what cards to keep, to close and to set aside, so you can take a big sigh of relief!

Plus, I'm giving you my free "5 Ways to Simplify Your Travel Rewards Strategy" guide. Text SIMPLIFY to 844-403-2263 to grab it. 

If you're tired of DIY-ing this alone and want a proven system that takes the guesswork out of flying free, join hundreds of families inside Families Fly Free at familiesflyfree.com/join.

Because you can't recall the memories you never make...

You’ll learn:

• Dave’s weekly habit that keeps spending responsible yet rewarding

• How he pushed through a points hiccup and why it was worth it

• Why smaller airports like Boise can still unlock big wins

• The quote that guides his travel: “You can’t recall the memories you never make”

Ready to make those memories with ease like Dave?
Join Families Fly Free to start using miles and points with ease so you can make more family memories by flying free forever.

👉 Start here: https://www.familiesflyfree.com/join

I discuss the simple way to avoid paid seat headaches — lost seats on changes, messy expiring credits and poor points-plus-cash value — by booking in points and using the right Southwest card so you get an assigned seat without paying extra.

I round things out with some good news: 

• free Wi-Fi for Rapid Rewards members starting today!

• new aircraft features

• new routes like Alaska and the Caribbean

Plus, I share what we do and don’t know yet about the Southwest Companion Pass for next year.

Want real-time answers to change in the travel rewards industry and a plan that fits your family's travel style? Join Families Fly Free for my simple Fly Free Formula, personal support and up-to-the-minute guidance — the price increases October 29. Get started at FamiliesFlyFree.com/join 🧳✈️

Related Episodes:

• 199 |❓Your Families Fly Free & Travel Rewards Questions Answered by Members: Open House Replay

• 193 | 🎯 Southwest Changes Simplified: New Fares, Assigned Seats, Bag Fees - Oh My!

• 186 | New Rules, Same Free Perks? How to Outsmart Southwest’s Changes

In this episode, I share a replay of a recent 🧑‍🧑‍🧒‍🧒 Families Fly Free Open House with 4 current members on hand to answer attendees' questions honestly and directly. We had a HUGE turnout and so many great questions AND answers from our amazing members.

Some of the questions included:

• Do I have to have a Southwest Companion Pass to get my value from the membership? (Answer: No ;-) - 2 of our panelists don't even have one!)

• Do I have to spend a lot of money on credit cards to earn all these points?

• Does it involve closing and opening a lot of credit cards?

• Does it work for international travel?

• Do I always have to fly Southwest?

• Is it worth it to pay the annual fees on travel cards?

• Is this a one-time fee or does it renew every year?

• And TONS more!

Dive into this episode to get all your questions answered about this life-changing membership and hear how it's about so much MORE than the information that will help your family fly free in the simplest possible way. It's the people, the real-time info, the support, the continuing knowledge you gain, the hacks and the list goes on. It's everything you need to not just learn, but take action and be successful year after year.

✅ Join Families Fly Free at FamiliesFlyFree.com/Join

Want an invitation to the next Open House? Get on my email or text alert list.
👉 Join my email list at FamiliesFlyFree.com/Email
📱 Get text alerts by texting FLYFREE to 844-403-2263 (no more than 1/week)

Still have questions?
Email me at info@familiesflyfree.com
Text them to me at 844-403-2263

Fresh off a Families Fly Free member meetup in California wine country 🍷, I’m sharing the simple, real-time strategy my Families Fly Free members use to keep flying free without juggling 20 cards or chasing outdated advice. You’ll learn why narrowing your focus is the fastest win: master flying free first, stick to one flexible ecosystem (hello, Chase), fly one primary airline (yes, Southwest still works when you know how) ✈️ and skip high-fee lounge cards and hotel cards until year two.

I’ll show you how “simple equals successful” and:

• Which cards to actually put your spending on

• How to adapt to airline changes without paying more

• Why you can stop nickel-and-diming every little credit. 

If you’re overwhelmed or short on time but want to travel more for less, this is your roadmap 🎯.

Interested in Families Fly Free? Attend my Open House on Zoom on Wednesday, Oct. 15 at 2pm ET, 1pm CT, Noon MT 11am PST and hear from current members, learn more about membership and ask your questions live! Register at FamiliesFlyFree.com/OpenHouse.

Families Fly Free is where I walk beside you — with live Q&As, texting, small groups and 1:1 support — so you stay current as things change. The price is going up soon, so now’s the moment to jump in and lock it in: FamiliesFlyFree.com/join.

You’ll learn:

• Why to compare portal prices vs. transfers in 2 minutes and pick the cheaper option

• The biggest pitfalls with third-party hotel bookings and how to avoid them

• My confirm-confirm-confirm, validate-validate-validate strategy

• Why Hyatt is the go-to sweet spot for fewer points and direct-booking peace of mind

Want my swipe files, step-by-step Stay Free Formula™ and real-time help and community support as things keep changing? Join Families Fly Free to stretch your points further with fewer cards and less hassle, so your family can make more travel memories together: https://www.FamiliesFlyFree.com/join

To stay on top of the lastest and ever-changing strategies in the world of travel rewards + learn my simple Fly Free Formula, join me inside of my hallmark Families Fly Free membership. Learn more at https://www.familiesflyfree.com/join

RELATED EPISODES:
87 | The Chase 5/24 Rule Explained
86 | All About Capital One Venture X

Listen in to learn:

• How to adjust when banks tighten, bonuses become limited and fees increase

• Which cards to keep vs cut

• How to shift your strategy so continual card bonuses aren't necessary (because that's no longer going to work!)

If you want ongoing, up-to-the-minute guidance you can trust — plus monthly live Q&As, real-time community-tested tips, and my step-by-step Fly Free Formula™ — join my Families Fly Free membership. I stay on top of the changes so you don’t have to 🧠.

Ready to simplify and always travel free? Join at FamiliesFlyFree.com/join.

Related Episodes:

193 | 🎯 Southwest Changes Simplified: New Fares, Assigned Seats, Bag Fees - Oh My!

68 | Stop Applying for Too Many Travel Cards! There's a Much Simpler Way...

From haunted hotels and mysterious lighthouses to tap-dancing ghosts and legendary pirates, you’ll discover plenty of places to explore this Halloween season without the gore. 

Whether you’re planning a fall getaway, looking for unique history lessons for the kids, or just love a good ghost story, this episode will spark ideas for memorable (and slightly spooky!) adventures.

Want to fly free to haunted hotels or pumpkin-filled fall destinations? Join Families Fly Free and I’ll show you my simple formula to make it happen: FamiliesFlyFree.com/join

Related Podcast Episodes:

• Episode 42: My Favorite Family Halloween Travel "Treat": Disneyland at Halloween

• Episode 43: Yikes! Universal Orlando's Halloween Horror Nights: Your Guide From a Mom's Perspective

• Episode 76: 5 Fun Halloween Getaways for the Spookiest Season

⭐⭐⭐⭐⭐ Thanks for leaving me a 5-star rating if you enjoyed this podcast episode! ⭐⭐⭐⭐⭐