Smart Money Podcast: Nerdy Travel Diaries: Getaway to Costa Rica

Kevin Berry
Sean Pyles
By Sean Pyles and  Kevin Berry 
Edited by Laura McMullen

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Welcome to NerdWallet’s Smart Money podcast, where we answer your real-world money questions.

This episode, Sean talks with NerdWallet travel editor Kevin Berry about his recent trip to Costa Rica.

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Our take

If you traveled in the pre-COVID times or used a travel credit card of some kind, there’s a decent chance you’re sitting on some points and miles that have accumulated over the last two years. When you’re ready to travel again, don’t immediately pay cash for those trips. Take stock of what points and miles you have lying around that might significantly limit the amount of cash you have to pay.

As Nerds, we deal with this, too. One of our travel editors, Kevin Berry, recently set out to book a big 15th wedding anniversary trip. Rather than shelling out thousands of dollars for flights and hotels, he used up a trove of Marriott Bonvoy points that had been building up over the years.

Through a combination of a welcome bonus, business travel, strategically paying cash for less expensive trips and crafty use of a fifth-night-free benefit, Kevin was able to turn his 370,000 Bonvoy points into a five-night stay at an all-inclusive resort in beautiful Costa Rica for him and his wife. You can do the same.

Our tips

  • Understand your hotel's free night policy: Several major brands will give you a free night when booking on points.

  • Use points for things you wouldn’t pay for otherwise: Many points-and-miles travelers like to brag about the “cents-per-point” rate they exchanged for. Don’t get too caught up in that game. Rather, focus on using your points for things you would not otherwise pay cash for.

  • Consider positioning flights: Depending on your home airport, it can sometimes make sense — logistically and financially — to book a separate flight to another city and then book your direct flight to your final destination.

Note that we mention a few credit cards that are NerdWallet partners, but that doesn't affect the way that we talk about them.

Have a money question? Text or call us at 901-730-6373. Or you can email us at [email protected]. To hear previous episodes, go to the podcast homepage.

Episode transcript:

Sean Pyles: Welcome to the NerdWallet Smart Money Podcast, where we usually answer your personal finance questions and help you feel a little smarter about what you do with your money. I'm Sean Pyles.

In this episode, we are continuing our Travel Diaries series, where we'll hear from our travel Nerds about the trips they've taken and the money they've saved along the way.

This time around, we are talking with one of our travel editors, Kevin Berry. Kevin is going to share the details of a luxurious international trip he booked for a wedding anniversary using points and miles. He'll also give some tips for how you can do the same. Welcome to Smart Money, Kevin.

Kevin Berry: Thanks for having me. Excited to be here.

Sean Pyles: It's great to have you on. And one quick note before we get into this conversation: We are going to talk about a few credit cards that are NerdWallet partners, but that doesn't affect the way that we talk about them.

So you had, as I mentioned, a luxurious international trip. Give us the details of it.

Kevin Berry: Yeah. My wife and I had our 15th wedding anniversary coming up, and we were just sitting on a pile of points — hotels, airlines, travel points — that had accumulated during the pandemic, because we just hadn't traveled, obviously, during the COVID times.

So with a big milestone anniversary and a bunch of points, it seemed like a pretty good opportunity to try and book something extravagant. And we had traveled pretty extensively domestically and been to the beaches of Mexico a lot. But we wanted to try something new for the anniversary, and we had a bunch of Marriott points.

So we set out to figure out how to burn all of those on a nice big trip that maybe we wouldn't normally pay for. And so we started looking at all-inclusive resorts.

Sean Pyles: Interesting. So it seems like you had these points and you let that dictate where you were going to spend them — the location of your big trip post-COVID, or semi-post-COVID, as we are.

Kevin Berry: Yeah. I mean, certainly because points, generally, they are not an investment. They devalue over time, and they expire. Hotels will change the amount of points it takes to book a hotel, making them less valuable.

So we want to spend the points that we had with the brand that we had, and Marriott was the major one.

Sean Pyles: Yeah, sure. And I think a lot of folks who were in a pretty similar situation and still are, with a lot of points built up over the pandemic, and they haven't been able to use them.

So can you walk me through your thought process on how you ended up picking that specific location? And what factors were the major drivers for you?

Kevin Berry: Yeah, sure. As is travel in the COVID era — that was always the first obstacle, right? Where can you get in? Not all countries are letting people in. What's your tolerance in terms of vaccination rates, and where do you feel comfortable going? You've got to have a COVID test to get back into the U.S., so how prevalent are those in the country you're looking at? So that was part of it.

As I mentioned, we knew we wanted to go to a Marriott, and we knew we wanted to go to an all-inclusive. That pretty quickly narrows you down to about 20, 25 resorts.

And I think the big thing that we were really looking for is: We wanted a place that — since we were using our points — we wanted a place that we would never pay for with actual money. Like to have an experience that we wouldn't shell out the cash for, but since we're using these points, it's something that you wouldn't get to experience otherwise.

Sean Pyles: Yeah, it feels like free money in some ways. And so you can spend it in perhaps a more luxurious fashion than you would your own dollars.

Kevin Berry: Right. There's no literal way for me to turn all those Marriott points into cash in my hands. I might as well use them to stay at a resort I wouldn't otherwise pay for.

Sean Pyles: Cool. So where did you land?

Kevin Berry: We ended up at a Weston all-inclusive in Costa Rica, which was a new country for us.

Sean Pyles: And we should clarify that Westons are Marriott properties.

Kevin Berry: Right. So it checked all the boxes: great weather, easy to get to, Marriott, all-inclusive and the COVID logistics were pretty manageable.

Sean Pyles: And Costa Rica is beautiful. So it's a great place to visit. It's actually the last spot that I traveled to internationally, August 2019. And I'm glad I was able to actually take that trip, because it's been a long time since I traveled internationally.

Kevin Berry: Yeah. It's hard to go wrong in Costa Rica. Anyone I talked to prior to the trip that had been, no one ever wavered. They were always like, "Oh, you're going to love it. It's fantastic."

Sean Pyles: It's unlike anywhere else. The natural beauty of the place, the Cloud Forest, the animals everywhere, the indigenous culture. It's incredible.

Kevin Berry: Yes, it definitely is. And you get a wide range of geography in that country too, depending on where you want to go.

Sean Pyles: Yeah, very cool. Well, let's get into some of the specifics of your travel plans and see what we can learn from your strategy.

So let's start with your hotel. What were the details of your booking, and what advice do you have for the rest of us looking to book big trips like this?

Kevin Berry: When I said a mountain of Marriott points, specifically it was 370,000 of them.

Sean Pyles: Oh, wow. OK.

Kevin Berry: So that …

Sean Pyles: It's a huge amount.

Kevin Berry: It is a lot, but that's not necessarily a unique situation to be in. Credit card sign-up bonuses — you can get 100,000 points if you qualify for those and meet the minimum spend. And I traveled for work quite a bit in my previous job, and those points had piled up.

So we took that and cashed it in for five nights at the Weston all-inclusive. This is a resort where the cash rate is $500, $600 per night. So paying $3,000 for a trip is just not something that we would normally do. Maybe some people travel like that. Good for them. That's not how we travel.

It was a fairly good use of our Marriott points. Here at NerdWallet, we do all these valuations of “What are your points worth?” and “What should you try and get?” And a Marriott point is worth about seven-tenths of a cent, per point.

And I got a little bit better rate of that, but I think the big thing that you want to look at when you're booking a trip is: You don't have to maximize the value if you're getting an experience that you wouldn't otherwise get.

And so that was really what it came down to for us. It was like: This is a good redemption, but we would never get to go here otherwise, and that's what made it enticing for us.

Sean Pyles: Yeah. So what was so appealing about that property itself? What were you getting from this booking where you said, "This is the luxury travel that we want"?

Kevin Berry: I think it was a combination of a couple things. First of all, in the Marriott system, you're able to get a fifth night free when you book. So we only had to pay four nights’ worth of points, but we got to stay for five nights.

So when you take that on top of a $500-, $600-a-night all-inclusive, and you've got this beautiful resort and these high-end restaurants, it just really starts to pencil out, because you feel like you're getting a good deal with the fifth-night-free perk.

And Marriott's not the only one that does that. Hilton has a fifth-night-free benefit. IHG has a fourth-night-free benefit. So it kind of gives you this opportunity to get outsized value, if you are strategic about the types of hotels that you pick to spend your points at. And you can do fifth night free at the Courtyard by your local airport, or you can do fifth night free at an all-inclusive in Costa Rica. So there's a little bit of strategy there that played into that.

Sean Pyles: I would love to hear a little bit about the other amenities of where you stayed in the location itself. For example, when I stayed in Costa Rica, my partner and I stayed in the Cloud Forest at a hotel there. And the hotel offered guided tours of flora and fauna at night. We did a night tour of the local jungle in the area, which was very beautiful.

But then we also stayed at an all-inclusive resort that had nothing of the sort. It was close to the ocean, but most folks stayed in the pool, which we found kind of baffling.

So did you get to experience the natural beauty of the area? What was that experience like?

Kevin Berry: Our trip was a little unique. The first two days and the first night that we were there, we actually stayed in this little beach town that was seven minutes from the resort. And we did much more of the local bed-and-breakfast, local restaurant, eating down by the beach and just walking around town.

And then we went to the resort for the five nights. And when you're at the resort, there's so much to do at the resort that we never felt the need to leave it. I now feel the need to go back to Costa Rica and do all the other things.

But the resort had these nightly shows, whether it was this like fire-dancing show or a Caribbean-themed show. There was coffee-tasting and drink-making. So there were all these different activities.

And really at an all-inclusive, at least at a high-end one like we had, we were fortunate enough to go to, the food became the activity, with the, “Where could we get the reservation for dinner tonight?” And you started scheduling around that, because the steaks were so good and the Italian food was so good. It became a foodie trip, really.

Sean Pyles: I kind of love when you're at a resort like that. And it almost feels like you're regressing back into your childhood, where you're just being fed and taken care of. And you don't have to actually make any decisions on your own, except for where your next meal is coming from.

Kevin Berry: Yeah, exactly. It was definitely like that, especially with the drinks just coming to the pool whenever you raised your hand.

Sean Pyles: Very nice. Well, did you make it out to the Cloud Forest at all when you were in Costa Rica?

Kevin Berry: We did not. Cloud Forest is on the next trip's list.

Sean Pyles: You got to do it. There are a number of ways to do it. Some folks will take a bus from San Jose. And we thought about doing that.

We ended up renting a car, because we had to drive beyond the Cloud Forest to where the actual resort was that we were staying at eventually. And if you like to drive off-road, and you're not scared of steep mountain roads, I would recommend it. It was a lot of fun, and it gives you a certain amount of freedom. It was a great time for us.

Kevin Berry: Very nice. Yes. I will take that recommendation to heart for my next trip.

Sean Pyles: Well, I want to go back to all of those points, because you accrued a massive amount of them. How did you actually get all of those Bonvoy points?

Kevin Berry: The big way — and this is open to most people and this is what we talk a lot about at NerdWallet — is credit card sign-up bonuses.

Marriott has cards with Chase and with American Express. And if you qualify, they give you a welcome bonus, or a sign-up bonus, for spending a certain amount of money in a certain time frame.

Now, obviously you want to do that and pay the bill on time. You don't want to incur interest charges, because then that takes the value away of the points.

But you can get upwards of 100,000 points or more, depending on the promotion they're offering. So that's part one.

And then part two is, depending on your financial situation, sometimes you want to pay cash for your trips. When we go to Mexico, and the rates are affordable — they're $100, $120 a night — we choose to pay for those.

And then, because we have status at Marriott and I have a Marriott credit card, I earn like 23 ½ Marriott points for every dollar that I spend. So you can do the math on 23 ½ times a week in Mexico — that starts to add up pretty fast.

And thirdly, I would say, if you travel for work, it's worth it to go out of your way to stay at a consistent brand, because those points start to pile up, even if your company's paying the bill. You're still the member, and you're still acquiring those points. So you want to consolidate those.

Between work trips, and paying cash, and earning points and credit card sign-up bonuses, getting to 300,000 or 400,000 points is actually not as hard as it sounds.

Sean Pyles: I want to talk a little bit more about the time that you spent in Costa Rica. You mentioned that you had some incredible food, some great coffee, which Costa Rica is known for. What else did you do during your time there?

Kevin Berry: We had a very different experience the first two days versus the last five days. And the first two days that we were there, when we were down in the beach town, little bed-and-breakfast, local restaurants, local coffee shops.

And that was just a really cool kind of, get a feel for what a beach town in Costa Rica is like. It was just a much different feel than once you got to the luxurious resort.

And once we got to the resort, it became all about the food. And there was a schedule every day of where you could get reservations. There was a schedule of activities every day. It was about finding what seat at the pool you could get and hunker down with for the day.

So there were some logistics involved with that. But yeah, it was just a very different experience being at this luxurious resort, but also getting to sort of experience the local Costa Rica vibe the first two days.

Sean Pyles: It sounds kind of “White Lotus”-esque without maybe the horrible snobbery, I'm hoping.

Kevin Berry: Yeah, exactly.

Sean Pyles: OK, cool. So how much did all of this cost — these activities during the day? And what did you do to save money?

Kevin Berry: Yeah, I mean, the beauty of an all-inclusive is much of it is already in the cost. Like, we didn't have to pay for the shows. Obviously, we didn't have to pay for the meals.

The only things generally, when you go to an all-inclusive — like if you want to go to the spa — it's extra. If you want to play at the golf course, it's extra. So other than some souvenirs, when we were on the resort, we didn't spend any money.

We really focused on getting the most out of our time on the resort. There was this cool bar, and they'd have music and dancing at night — no cost. No cost for the drinks, no cost to show up.

That's the bonus to an all-inclusive, right? You remove this decision-making and it sort of allows you to just enjoy the trip a little bit more, because it's just all included there.

Sean Pyles: One tip that I have for folks who might stay at an all-inclusive resort like this is to buy sunscreen before you arrive at the resort, because that's something that I did not purchase before I got to my resort in Costa Rica. I ended up having to buy some there, and it was $50 for a not-big bottle of sunscreen, which you had to have.

So that might be one tip. Stop by the local pharmacy before you get there, because once you land there, you're not going to want to leave.

Kevin Berry: Yes, exactly. We did just that. The day we were in the beach town, we hit up a local grocery store and picked up essentials and the sunscreen was very reasonably priced down there.

Sean Pyles: Not $50.

Kevin Berry: No, not $50. We got waters and sunscreens and all the toiletries that we didn't want to pack. It was like $60 for all of it. And, yeah, not bad. And it was enough sunscreen to get us through the week, and it was great.

Sean Pyles: Cool. So Kevin, when it came time to book flights, what was your thought process there?

Kevin Berry: Flying in this COVID era, especially with all the reductions that have happened staffing-wise with airlines, we were legitimately nervous. Because, I mean, look, we read it in the news all the time about flights getting canceled and delays. And nobody wants to miss a connecting flight when they're going on vacation, right, and you've spent 370,000 Marriott points — you want to get there on time.

So we chose to mitigate some of that. I live in Portland, Oregon, and it's not a direct route down to Costa Rica. So we booked a separate flight into Denver, because we could get from Denver to Costa Rica direct.

And we just went a day early. And we just used a free-night certificate at an airport hotel. So that way, we knew we were in Denver the night before the flight, we were on a direct flight to Costa Rica, and that mitigates a lot of the risk of missing a connection or something going wrong.

And it all worked out and we got there on time, but just less stress on our end. And normally when you price it out, it doesn't cost more. Sometimes it's actually cheaper because you've got some flexibility.

Like, I can pick the cheap flight from Portland to Denver to get there, and then I buy my ticket Denver to Costa Rica and it ends up being cheaper than the airline routing me there themselves.

Sean Pyles: Yeah. And I think the fact that you could get a practically free hotel that night makes a big difference as well. Because I was looking to book some travel from Portland to London for the summer, and I was considering flying into Chicago first, spending a night there and then flying from O'Hare to Heathrow, because O'Hare is such a big international hub.

I ended up looking at the price of a hotel and everything else that was going to be involved in it, and it didn't make sense for me. I think because of lodging alone, it really pushed me over the edge.

And I said, "OK, I'm going to spend a few hundred bucks more for a flight straight from Portland to Heathrow, but in the end, I'm coming out ahead." So the fact that you had some points to use, I think makes it worth it for you.

Kevin Berry: Yeah. And I also encourage people to check your hotel accounts, because you might have free-night certificates you've forgotten about. You may have earned them through a credit card perk you used to have.

There's various ways, depending on the brands, that you get these free-night certificates. And they're usually only good for a certain level of hotel, a certain amount of points per night. But those airport hotels are usually on the cheap end, and that's sometimes a good way to burn those.

Sean Pyles: Right. All right, that makes sense. Well, so what about your return flight, and how did that go?

Kevin Berry: We had an interesting return flight. We were similarly booked Costa Rica direct back to Denver. And [on] our airplane on the way back, the toilets stopped working.

Sean Pyles: Oh no.

Kevin Berry: And our flight almost got rerouted to Houston, which obviously would have caused us to miss our connecting flight to get back home. And the pilot came on and explained the situation. And there was very much the sentiment on the plane of like, “We all need to get to Denver; we're all just going to hold it.”

And we did. We got to Denver, we all stopped using the toilets for like an hour and 20 minutes. And the airline was good, to their credit. A week later, we all got $100 vouchers for the inconvenience. So that's, you know ... Yeah, we'll take that.

Sean Pyles: That's nice. It could have gone a very different way. So I'm glad it wasn't that big of an issue.

Kevin Berry: It definitely could have. And then once we got to Denver, we were actually on United Airlines from Denver to Portland, and we got upgraded to first class for free, which was great.

I have Silver status with United, which I actually got as a benefit of being a Titanium member with Marriott. This is a thing that I think gets overlooked a lot of times: If you have status through whatever — through your work, through a credit card, or you just earned it — you might have Elite status with one of their partners as well. And sometimes you have to activate that.

So there's a page on the Marriott site to activate that Silver membership for United. And just by doing that, we got fortunate and got upgraded to first class for the ride home for no additional cost. So …

Sean Pyles: That's pretty cool.

Kevin Berry: Yeah. You want to know what your options are.

Sean Pyles: How can folks know what their options are? Because these various platforms can be kind of confusing to navigate, because there are all of these different relationships between different companies. What did you do to figure out that you had that opportunity?

Kevin Berry: First of all, if you have Elite status somewhere, go look at their membership page. Go look at the Marriott Titanium page, or go look at the Alaska Airlines Gold page, or whatever it is that you have. And they're pretty good at explaining what those benefits are.

And shameless plug: Check out NerdWallet's content as well, because we have Elite status articles about all of these airlines and hotels that will lay out what comes with them and what else you might be able to get with them.

And the second thing I would say is … check with your employer. A lot of companies have travel benefits because of larger contracts or deals that they have with travel agencies or the airlines directly.

My wife, for example, has perks on three or four different airlines through her work, but she has to opt into it. So you need to know about them, and you have to give them your frequent-flyer number in order to trigger those benefits. So ask your HR rep, ask your travel person, or however your work is set up, and see what you might have access to through work as well.

Sean Pyles: Well, I would love to hear about your favorite moment of the trip.

Kevin Berry: That's a great question. I'm going to cheat and give you two favorite moments.

I think the first one that comes to mind was the first dinner meal that we had there on the first night. We didn't know what we were in for, I think. We knew we were at it all-inclusive, but we didn't know about the quality of the food.

And we went to a steakhouse, and the filet mignons came out, and you cut into that for the first time, and we were like, "Oh, this is what we're in for all week." That's when the light bulb went on that this was not going to be average food. This was high-level stuff.

I would say that, and then also just the first night of the trip in the beach town, walking through the little local town and eating at the beachside restaurant, at sunset. It was just a really low key, Costa Rica beach vibe.

What a great way to start a trip and just relax and just sort of reset yourself. And especially [because] we've all been through a rough two years. And it was great to finally get away and feel safe about it. Those are the two that stick out to me the most.

Sean Pyles: Yeah, I totally relate to that last one. Sometimes when you have that moment on a vacation where you're with someone that you love and you really take in the place that you are in together, can be so meaningful, especially after all that we've been through over the past couple years.

Kevin Berry: Yeah, for sure.

Sean Pyles: Well, Kevin, do you have any takeaway tips for our listeners?

Kevin Berry: One, if you're going to book hotels, make sure you understand your hotel's free-night policy. Like we said earlier, Marriott and Hilton: If you're booking on points, your fifth night's free. IHG: fourth night's free. You can get a lot of outsized value and extend your trips for no cost when you do that.

Number two would be: Use your points to take trips you wouldn't otherwise be comfortable paying for. That's the time to splurge is when you're not spending "real money" on a trip.

And I would say this, and we haven't talked about this yet, but don't be afraid to spend money when you need something that is quality. And I say that in the sense of: We spent money on transportation to and from the airport. We didn't try to be cheap about it. We didn't try and, like, frugal our way through it, because it was an hourlong ride, and we got private van transportation. We had great guides that got us there. As you mentioned, the roads in Costa Rica can be quite bumpy and hard to navigate, and that was just well worth it.

So there's times to be frugal, there's times to use your points and then sometimes you just need to pay for something really good. And that's OK.

Sean Pyles: Just to make things easier for yourself. That makes sense.

Kevin Berry: Yeah. There's certainly a convenience factor and just not having to worry about certain things. If you have the money to solve a problem, you no longer have a problem. So don't be afraid to spend it if you have it.

Sean Pyles: All right. Well, thank you so much for sharing your story with us, Kevin.

Kevin Berry: Thanks, no problem. And that's all we have for this episode.

Do you have a travel or money question of your own? Turn to the Nerds, and call or text us your questions at 901-730-6373. That's 901-730-NERD. You can also email us at [email protected].

Also, visit for more info on this episode. And remember to follow, rate and review us wherever you're getting this podcast.

Sean Pyles: And here is our brief disclaimer, thoughtfully crafted by NerdWallet's legal team. Your questions are answered by knowledgeable and talented financial writers, but we are not financial or investment advisors. This Nerdy info is provided for general educational and entertainment purposes and may not apply to your specific circumstances.

Kevin Berry: And with that said, until next time, turn to the Nerds.