4 Trips We’re Planning with Credit Card Rewards

Trips We're Planning with Credit Card Rewards - picture of Interlaken

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I’m pretty sure most of our friends think we’re workaholics. Truth be told, they may not be that far off, but it’s not like we don’t have any hobbies.

A few weeks ago, one of my friends asked what we like to do for fun. I said we enjoyed travel, spending time with the kids, and working.

“But what do you do for fun?” was his reply.

Well, we like to travel. And spend time with the kids. And dream up new plans for our business. And plan our travel. It’s what we do, it’s how we relax, and it’s what we enjoy. It’s also why we’re able to travel for pretty close to free.

Of course, we also love to help others save, which is why we offer free travel advice. Finding ways to save is an enjoyable challenge for us, plus it provides a huge sense of satisfaction to help others save on their dream vacations. Just a few days ago, Holly helped a reader save about $1,200 on airfare for their family trip! Needless to say, our reader was thrilled.

In the spirit of sharing travel stories and having fun, we want to pull back the curtain on some of our upcoming adventures. Better yet, we’ll show you how we’re using credit card rewards to cut down on costs. Hopefully, you’ll pick up a few ideas you can use yourself. Enjoy!

Where We’re Traveling on Credit Card Rewards

St. Thomas

This fall, we’re headed to the U.S. Virgin Islands for the first time…and we’re taking the family! I’m super excited for this trip because St. Thomas looks absolutely stunning. I even geeked out by watching the old Real World season in St. Thomas. #guiltypleasures

We booked a couple of condos through VRBO which are located right next to the famed Sapphire Beach. Like, we can literally walk down the beach and be there in less than 5 minutes. We’re also going swimming with sea turtles and taking the ferry over to St. John for the day. I can’t wait!!!

As I mentioned, we’re taking the family with us – including Holly’s mom and dad. That means we needed 2 condos, a rental that seats 6 (plus luggage), and 6 airline tickets. The condos weren’t too bad, but renting a 6-passenger van on St. Thomas is a little steep. We checked around but couldn’t find a better rate than what we found on Expedia. For our flights, we’re using some Citi Thankyou points, a credit we got from American Airlines, plus some cash. If you want to be nosy, you can check out the condo we’re renting here!


Oh. My. God. As a former theatre major and straight up history dweeb, this is seriously a dream trip for me. Toss in a the fact that I’m an Olympics fanatic, and I can’t tell you how freakin’ stoked I am to go to Greece. This ridiculous trip is also taking place this fall, and it can’t get here fast enough.

For our first day, we plan to stay in the Plaka district in Athens. From there, we’ll have awesome views of the Acropolis (which we’ll obviously be visiting) and access to all kinds of yummy restaurants. Then, we’re going on a 4-day tour of mainland Greece that we booked through Viator. This is the first time we’re taking an extended tour, so we’ll let you know how we like it. During the tour, we’ll be seeing places like Olympia (where you can bet your bosom I’m going to run on the original Olympic track), Delphi, and Meteora. After that, it’s back to Athens for our last day.

As with most of our trips to Europe, we’ll be flying coach with American. We have a ton of AAdvantage miles, but flights are ridiculously cheap right now. For us, it made more sense to book with general travel points instead. Our flights cost about $650 round-trip each, which we paid for using points from our Citi Prestige and Citi ThankYou Premier Cards. If you aren’t sure where to find them, you can compare the best rewards cards here.


It’s official. We’ve decided to head back to Montego Bay, Jamaica for our annual Spring Break trip with the kids. Once again, we’re staying at the Holiday Inn Resort, Montego Bay All-Inclusive…and we’ll be saving money by paying for some of it with points.

We absolutely adore this place. The rooms are nice, the beach is wonderful, and the food is pretty darn good for an all-inclusive. This place is extremely family friendly, and it will be our third trip here. Our kids swim like fish, but we still don’t want them to fight choppy water. At this resort, there is a small island and a reef that blocks the rough surf from hitting the beach. It’s awesome, and it allows us to relax and watch the kids play from the shore. You can read our complete review of the Holiday Inn Resort, Montego Bay here.

Getting to Jamaica cheaply is easy, especially if you have some Chase Ultimate Rewards or Southwest miles to burn. We’ll transfer some of our Ultimate Rewards points to Southwest and fly the four of us down using that. If you haven’t had a Southwest credit card, you can pick up a ton of points using one of those too.

Additionally, we’ll transfer a few more Ultimate Rewards points to IHG to pay for the hotel. We haven’t booked it yet, but I’m sure we’ll choose the points and cash option, making our stay about $70 per night. I think that’s great considering all of our food, entertainment, and drinks are included. For more on how to earn Chase Ultimate Rewards points, read our complete summary by following the link.


I think we’re finally doing it. We’re going to Europe next summer for about 3 weeks…and we’re taking the kids with us. The kids are excited to get another stamp in their passport and see some “real castles” for the first time. (I can’t wait to see their faces when we take them to Mad King Ludwig’s fantasy castles!) Holly and I are excited check out Bavaria and the Swiss Alps before heading back to Italy for the second time in 18 months.

We’re still contemplating the best itinerary, but the tentative plan is to fly into Munich and out of either Rome or Naples. If we find better flights starting in Italy, we’ll reverse course. Anyway, we’ll spend the first few days in Munich, then head down to Lucerne and either Interlaken or Gimmelwald in Switzerland. From there, we plan to hit Lake Como, Cinque Terre, Florence/Tuscany, and then Rome. We’re also considering another trip to Capri or Pompeii for a day. It’s going to be epic, and we can’t wait.

This type of trip is obviously going to require some serious cash. We know we’re going to have to pony up some money, but we haven’t figured out exactly how much yet. But if you know us, you realize we’re already using our best budget travel tips to pile up points and save money on the trip.

We’ve started compiling a buttload of American Express Membership Rewards points using our American Express Platinum and American Express Business Platinum Cards. By the time we’ve collected all the points for signup bonuses and spending, we should have about 315,000 points to burn. Those points transfer to over 20 travel partners, but I think we’ll probably use them for flights. We can claim them as a credit for about $3,000 in flights, which will certainly come in handy.

Read More About Your Favorite Travel Cards Here!

Wrapping Up

Traveling the world is one of the biggest motivators that drives us to work so hard. We love seeing new places, experiencing new things, and introducing our children to new cultures. Taking time to prepare and getting the most out of our credit card rewards helps us to do the things we love on a pretty grand scale.

We hope you’ve enjoyed this sneak peek at our upcoming travels! Let us know if you have any questions, or click here for help planning a trip of your own!

What trips do you have planned? Are you using rewards to help pay for it? Sound off in the comments!


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  1. These trips all look amazing! I went to St. John with my family during my junior year of college and I loved it. Even just snorkeling outside of the flat we rented was super cool. My boyfriend and I are planning a trip to Europe next year. We have friends in London, Berlin, Amsterdam, Brussels, and Zurich we’ve been meaning to visit for years. Luckily, we’ve saved about $2,000 in credit card points we’ll use for flights. Then, we’ll probably crash with friends and stay at Airbnb.

    1. Sounds like you have a good plan Kate! Plus, you still have time to earn even more rewards or cash back to save for your trip. See you in SD!

  2. Those look like some awesome trips Greg! Y’all will love Germany/Switzerland – I’ve been there twice and there’s just so much to see/do there and the kids will love it. We’ve got a few domestic trips planned out for the next 6 months or so, but Nicole is really wanting to take the kids to Europe for an extended period of time so that’ll likely happen next summer or maybe the following summer.

    1. Nice! I can’t wait to go to Germany and Switzerland. I’m so excited for that trip. It’s going to be a long haul, especially with the kids, but it should be incredible.

  3. You guys are living the dream! Amazing what can happen when you making certain choices and work hard. Do you guys like being workaholics? Are you guys the type that feel their job is their passion?

  4. Looks like some awesome vacations planned! It’s all well-earned from the all the work you guys are putting in!

  5. Those look like awesome trips! For the rental car, did you try searching on the Chase Ultimate rewards travel portal. I used it once to book a rental because all the other sites were more expensive. I paid cash and didn’t use Ultimate rewards but the price was definitely the lowest out of all the other travel sites.

    1. Yeah, we tried every place we could think of to find a cheaper car…but alas, it’s just freakin’ expensive there.

  6. We lived in Germany for 4 years and LOVED it! Your Europe trip sounds like it should be a blast. It was so easy and affordable to travel around while we lived there, so we took a trip almost every month. Have fun with the planning. There are too many good spots to choose from.

    1. Yeah, unfortunately we won’t get to see a lot of Germany. We’ll probably just hit the Bavaria/Munich area for a few days, then head down to Switzerland. I’m sure we’ll go back again and see the rest of the country!

  7. Yesss – I love all your trips. Greece is on my list for next year and after going to Jamaica last December, I think we’re gonna do it again this year 🙂

    1. I can’t wait for Greece…and I love Jamaica! We keep heading back there every year 🙂

  8. You have a great line-up of trips! Thanks for sharing.

    We haven’t made any plans for next year yet, but need to get moving on that. I appreciate the feedback on the Holiday Inn at Montego Bay – I think our kids would love it!

    1. It is perfect for kids of all ages. This upcoming trip will be our third time there!

  9. That castle in Germany is unreal. We’ll be headed to Asia this winter (50k American points round trip) and Europe next summer/fall (60k United points). We’re doing some hotel hacking, too (Carlson, Marriott, Hilton) but we’ll still have to use some AirBNBs…which we kind of like, too.

    Travel hacking is the best, right?

    I have a somewhat critical article of the travel hacking practice in the works, but it’s weird (and hypocritical) because I engage in it. Still, overall the benefits outweigh the downsides, IMO.

    Enjoy your trips!

    1. Yeah, we love hacking whatever we can. It has definitely helped us see more than we could have otherwise done. Of course, it is getting harder and harder to do.

      I can’t wait to see that castle! It’s going to be epic. Enjoy Asia and Europe!

  10. LOVE this list! I signed up for 3 credit cards this month. We have some big expenses in September and I plan on just putting everything on those! 🙂

  11. We’re going to have a baby in October and be grounded for quote a while. In the meantime, I’ll be saving up for a 2-week RV trip in June 2017. Any way I could do that with points?

    1. An RV trip sounds right up my alley! I’ve always wanted to do that. I’m not sure about points, but you could save up some cashback to spend. You’ll need to hit up Holly for some creative ideas!

  12. Umm those trips sound amazing! We are planning a trip to Europe next Summer but that’s it. I’m sure we will travel more once Victoria is done with grad school. For now it will be weekend/short-term trips and a big Summer trip.

    1. That’s it?!? Sounds like a huge trip to me! You’ll have a blast. Have you decided on where you’re going yet? Last I heard, I think you were considering Italy or the UK.

  13. If you do plan to rent a car, just be aware, that you need a “toll” sticker to drive on the autobahn in Switzerland. Maybe your rental car will have one, but if not you’ll have to buy one upon entering the country. Same thing if you go into Austria (which I would recommend, I love that place).

    My wife and I love Germany (it helps we have friends over there and she is fluent). You’ll have a great time!

    1. Ooo, thanks for the tip! We’ll have to keep that in mind. I think we’re planning on using the train through Switzerland, but we haven’t looked that much into it yet.

  14. These trips sound amazing! We’ve recently started travel hacking so our rewards are not even close to these yet. All of these places are on my bucket list and I think Germany/ Italy will be our next big trip so I will definitely be looking into doing some travel hacking for that vacation. I am pretty jealous of all of the amazing historical sites that you will see and amazing food that you will eat. Hope you have a blast!

  15. The trips are impressive but WAY too short time to learn or feel anything. It’s just like a ‘breeze through’ that’s all. Yep, I’ve been in Greese a gazillion years ago and dream to return there because 2 weeks were not enough for me.
    Brace yourselves for prices in Switzerland :-). Better get some smoked meats, fruits or whatever that doesn’t perish fast in Germany.

    Have fun. I’ve noticed that since this travel hacking came along I don’t think that Americans even sincerely appreciate traveling that much. It’s more like business opportunity “Hey, I went they, it was cool, not click on the CC I recommend so I get a commission on it” :-P. Bloggers must be competing with each other who got the coolest place visited lately. Hope you’re taking your kids to show the world.

    1. Thanks! I’m sure we’ll have a blast. Unfortunately, we don’t have the time to go at too leisurely of a pace. Living on this side of the pond and having kids means we can’t spend weeks at a time in one place. (We can’t wait to take them with us to Europe next summer though!) Of course, we don’t get to see everything, but we definitely go slow enough to get a feel for the culture and learn about the history behind what we do see. Luckily, we can always go back if we really love a certain area 🙂

  16. Having been to Switzerland, it\’s incredible to think you could do a trip with mostly credit card rewards. i was blown away when I saw the price of a big mac meal there: $15 after tax is included. Prices are a whole nother level of ridiculous there. We are going on a trip to DC with points thought soon

    1. Yeah, we’ll probably end up spending some money there…but we’ll just make sure to budget for it 😉 Can’t wait to experience it!

  17. You guys have some awesome trips lined up! My last large trip was to Dominican Republic in May. I used credit card points to pay for the flight and found an awesome condo (on a resort) through VBRO.

    My next big trip is next year to Spain. I plan on saving a majority of my points until that trip!

    1. The DR was our first international trip together, and that was only a few years ago! Loved it there. Spain is definitely on our list too. We’re very tentatively looking at heading there in 2018, possibly with a swing through the southern and central part of France too 🙂

  18. Tara Esposito says:

    In your opinion, what is the best credit card to apply for to get free airfares to Europe next fall?

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