Family Travel Unpacked: Make the Most of Travel With Kids

Hawaii vs Costa Rica: Showdown in Paradise

• Melissa Conn • Season 1 • Episode 31

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Hawaii vs Costa Rica for families: a real comparison of cost, activities, logistics and accessibility — plus which one we chose for our winter break.

If you've been going back and forth between Hawaii and Costa Rica for your family's next trip, this episode is for you. I've taken my family to both destinations.  After an embarrassing amount of research comparing both destinations for our upcoming winter break, I'm sharing everything so you don't have to do it yourself.

We cover flights and time zones, a detailed cost breakdown, activities for families, logistics and itinerary planning, the best time to visit each destination, accessibility considerations, and which destination we chose for this winter.

In This Episode:

  • Why where you live completely changes the flights and time change math
  • Accommodations: why Costa Rica wins on cash but Hawaii wins on points
  • How to search for award flights (and what the tools miss)
  • Activities: where Hawaii wins and where Costa Rica pulls ahead
  • Why itinerary planning in Costa Rica is a completely different challenge than Hawaii
  • Seasonality: what "dry season" actually means and where to go when
  • Accessibility: what traveling with a grandparent taught me about these two destinations
  • Our final decision for winter break — and why

Whether you're planning for next spring break or still dreaming, this comparison will help you figure out which destination is right for your family. Find the full blog post and more planning resources at thefamilyvoyage.com.


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Hey there and welcome back to Family Travel Unpacked. I'm your host, Melissa, and in case you're new here, you can always find tons of detailed destination guides, travel tips, hacks, and more on my website, thefamilyvoyage.com. And if you've been enjoying the show, be sure to hit follow wherever you're listening, so you never miss an episode. Today we're tackling a debate I know a lot of families wrestle with: hawaii versus Costa Rica. Two incredible tropical destinations, both wildly popular with families and both offering beautiful beaches, wildlife, and outdoor adventure. But honestly, they're very different trips in a lot of important ways. This isn't a hypothetical comparison for me. We've visited Hawaii with a baby with little kids, tweens and teens, and most recently on a big multi-generational trip with over a dozen people of all different ages. We've also been to Costa Rica as a family of four- we went last March during spring break. But the big question I had to answer for our upcoming winter break was whether to take that huge multi-gen group back to Hawaii or to try something new and go together to Costa Rica. Honestly, it was a really hard choice. And going through the decision making process is exactly what sparked this episode. I spent an embarrassing number of hours going back and forth on it, and by the end of the episode, I'll tell you what we decided. So stick around to find out. The first thing most families wanna know is how hard is it to get there? Because with limited vacation time, travel days matter a lot. And the honest answer is it depends on where you live. For East Coasters, Hawaii's a serious commitment, especially with kids. Even if you were in a major hub like New York, DC or Chicago with access to a nonstop, you are looking at nine or 10 hours in the air. If you have to connect- and most people in the country do- you're lucky to piece together an itinerary that comes in under 12 hours. That is a long travel day with kids, and I tell you that because we've done it twice. Costa Rica is a completely different story. If you're in Florida, Texas, you could be sipping a cup of incredible Costa Rican coffee just three hours after takeoff. When we went last year, we flew from Orlando and we actually got to a coffee farm in time for brunch. From the Midwest and the Northeast Nonstops run five to seven hours. And here's something a lot of people don't realize until they look at a map. Costa Rica is much further east than you think. San Jose, the capital, is basically at the same longitude as Atlanta. So from Columbus, where we live, we can get there in under seven hours, even with a stop. Of course, if you're coming from the west coast, a nonstop to Hawaii is less than seven hours, just a hair longer than those nonstops to Costa Rica. So your home airport really does impact the math, but your destination within Costa Rica also plays a role just like it does in Hawaii. There are two international airports in Costa Rica, San Jose in the center, and Liberia in the north. If you live in Seattle, you can fly nonstop to Liberia in seven hours, same as Hawaii. But getting to San Jose is a 12 hour ordeal because you'll have to stop. So there's a lot to think about. the other piece of the puzzle is time changes, and this one really matters for how quickly your family gets into a groove on the trip. Both Hawaii and Costa Rica don't observe daylight saving time, so the time difference depends on the time of year. Here's the takeaway. Everyone in the continental United States has a minimal time difference with Costa Rica, it's a max of two hours. And if you're in central or mountain time you literally have zero time change for half the year. Hawaii, on the other hand, is five to six hours behind the East Coast. That's a huge impact no matter how you slice it. I've experienced that time change from the east coast firsthand. And I'll be honest that it's rough. You're waking up at three in the morning, starving, struggling to make it through a luau, and by the time you've adjusted, you're basically packing to go home. For Costa Rica I think it's just easier to make the most of your trip because you can hit the ground running. So for this category, I give the edge to Costa Rica for East Coasters and Midwesterners, and I'll call it a toss up for the West coasters out there. All right, this is a big one. Let's talk money, and I'm gonna break it into four categories, accommodations, flights, activities, and food. I wanna start with something that genuinely shocked me when I was doing research for upcoming winter break trip. I went back and priced out the exact same properties in Hawaii that we stayed at and considered in December 2024. We're talking same week on the calendar and same room types. The prices had literally doubled. I booked 11 months in advance last time, and I gave myself roughly the same lead time this year, and I'm honestly still kind of in shock. I mean, I knew prices for Hawaii had gone up, but I hadn't really expected them to double in such a short time. Now, in general, Costa Rica gives you much more bang for your buck on accommodations. Back in the spring, we had to book a last minute hotel an hour outside of San Jose and I found a really lovely bed and breakfast for a hundred dollars per room. Good luck finding that anywhere in Hawaii. For our upcoming trip, I did a head-to-head comparison. A gorgeous three bedroom ocean view condo in a fancy part of Costa Rica is 60% less than a one bedroom condo with no view at the popular Honua Kai complex on Maui for the same dates. Let that sink in. Now if you're into luxury properties, the math isn't quite as clear cut. I compared two awesome properties that we've stayed at in the past year, the Andaz Maui at Wailea, and the Andaz Papagayo in Guanacaste, same brand, and I'd say similar level of luxury and service. The Maui one is actually a little bit cheaper for winter break, but both of the prices are eye watering. When you compare something like the Westin Hapuna Beach on the big island versus the Westin Reserva at Conchal all-inclusive in Costa Rica, the Costa Rica property is a little bit cheaper, but the price includes all of your food and drinks. So that's a huge difference. Here's where I give the nod. Back to Hawaii, though. If you're booking hotels on points, there are so many great options. Hilton, Marriott, Hyatt, IHG, and we're talking all over Waikiki, Maui, the big island, and even a few on Kauai. You can really stretch your hotel points in Hawaii, or you can blow your entire stash on an aspirational stay. Now Costa Rica has some fantastic points properties, but the selection is kind of slim. Near law Fortuna, the one and only option on points is the Tabba Con Thermal Resort through Hilton's SLH portfolio. It's supposed to be amazing. My friend stayed there with her kids and they loved it. But if it's sold out for your dates or it's just not your vibe, you're outta luck. It's the same story around Manuel Antonio, where Los Altos is basically your only option, and that's part of Hilton's SLH portfolio. So if you wanna use points in Costa Rica, I'd say Hilton is your best bet for adventurous destinations and Marriott is better for the beaches in Guanacaste. There's a Westin, a JW and a W resort out there, but those aren't gonna give you that classic Costa Rica experience that you might be thinking about. That area is a dry tropical forest. Here's one trick worth knowing that I've talked about on the show before. American Express membership rewards points transfer to Hilton at a one to two ratio. So a 100,000 point welcome bonus on a new Amex card can become 200,000 Hilton points. That goes a long way. And Hilton also gives you the fifth night free on points stays if you have any status above the base member level. You can get gold status automatically with certain credit cards that I'll link to you in the show notes. And if that's the kind of trick you wanna learn more of, be sure to head back to my episode that's all about hacking hotels. So in terms of points availability, I think Hawaii is definitely better. But if you're a cash payer, Costa Rica is gonna give you a lot more bang for your buck. Moving on to flights, the costs are all over the place depending on your home airport and the time of year. So I'll give you our example, Columbus to Maui for winter break, the cheapest one-stop itinerary I've found so far for our schedule is nearly$2,000 per person. Yikes. Columbus to San Jose was closer to 1500 round trip. For New Yorkers, it's even more dramatic. Costa Rica comes in about$1,200 cheaper per person than flying to Hawaii. From the west coast, though Hawaii wins in terms of cost. Sometimes you can get those round trips for as little as, let's say, 250 or$300. I'd say both destinations are solid for award flights. Use award tool, or points yet to search availability and get a sense for what's out there. Neither of those tools captures Southwest or British Airways, so be sure to check those separately. And no matter what, you should verify availability before you transfer any points from your credit cards. Don't sleep on that Southwest Companion Pass, by the way. We've used it for both Hawaii and Costa Rica and it's a huge money saver. Activities in Costa Rica are a bit lower priced. Guided Land Tours run, let's say 50 to a hundred dollars per person. Boat tours are a hundred to 150. Hawaii boat tours can run 200, sometimes even$300 if you're looking for a more intimate experience with a meal included. But here's the thing, you'll probably end up spending about the same total amount on activities because there are just more situations in Costa Rica when you'll wanna do a paid tour. The wildlife viewing, zip lines, some of the hot springs, it adds up. Thankfully both destinations have tons of free things to do, like beaches and hikes. So you can definitely offset some of that expense. Food is another area where Costa Rica really pulls ahead in my opinion. Hawaii is expensive for food across the board. Even groceries can be brutal, like$8 for a gallon of milk, or$6 for a loaf of bread. And restaurants? It's honestly hard to find a lunch option anywhere in Hawaii for under$15 per person. Uh, like our family loves coconuts fish Cafe in Kihei. It's casual, nothing fancy, but a basket of two fish tacos is$20. Even a sandwich at Leoda's Pie Shop is 15 plus. In Costa Rica, you can walk into a local soda- that's what they call the small casual restaurants that you'll find all over the place- and you can get a full Casado for$10 or less. That's a plate of chicken or beef served with rice, beans, salad, plantains, and a fresh tortilla. It's a lot of food and a great price. On the other hand, resort dining in Costa Rica can be just as expensive as anywhere in the us. My daughter ordered steak tacos at the Andaz Papagayo, since that was one of the only gluten-free options available, and they were$26. But the mid-level dining options in Costa Rica are dramatically cheaper than anything comparable in Hawaii. The bottom line on cost is that Costa Rica's the clear winner for most families, especially if you're coming from the East coast or the Midwest. Now, either of these destinations will keep your family busy for a full week. There's no question about that. But they each have some unique strengths. Both destinations have gorgeous beaches in a variety of styles. Calm lagoons, perfect for little kids, snorkeling spots, surfing black sand, white sand, golden sand. If beaches are your primary focus, I'd give the edge to Hawaii, and there are just so many incredible options and you could spend the entire trip just bouncing from one to the next. All of the beaches in both Hawaii and Costa Rica are technically public and free to access. But it's worth noting that in Costa Rica, some of those beaches are technically accessible to everyone but the practical path there involves walking a rugged route or crossing on shore at low tide, while easier access is available for resort guests or club members. In Hawaii, the law requires reasonably straightforward access, even to beaches that are adjacent to private resorts. Like we've driven over to the Mauna Kea Beach Hotel and the Ritz-Carlton Turtle Bay, and just parked in their lots to go to the beach. It's fine and legal as long as you're using the designated public parking spots. On the water in both places, you can do whale watching snorkel tours, sunset cruises, kayaking, fishing charters, and more. And back on land, you've got horseback riding coffee and chocolate tours, plus hiking through incredible forests and around volcanoes. But for sheer variety and adventure, I call Costa Rica the winner. You've got zip lining and Hawaii has just started offering it, but it's nothing like what Costa Rica has- plus whitewater rafting, waterfall, jumping, hot springs, and some of the best wildlife viewing anywhere in the world. You'll see sloths, monkeys, reptiles, incredible birds, and more all of that in their natural habitat, not just a zoo. So here's my take if you think you'll only visit each destination once, go to Hawaii when your kids are younger and you're looking for a more relaxed trip, and save Costa Rica for when they're a little older. A lot of the most unique Costa Rica experiences are a lot harder with a toddler or a preschooler in tow. And if you're really lucky, you can visit both at multiple ages to experience what they're like from a different perspective. Let's talk about a different aspect of the whole calculus: in my experience, planning a Hawaii trip is relatively straightforward. Pick your island or islands, book flights, choose a hotel, arrange a rental car, and I strongly recommend a car unless you're staying in Waikiki. And then as your trip gets closer, you can lock in any activities that you want. The big decisions you have to make are things like which resort area suits your family, or which luau to book. It's honestly really manageable. But Costa Rica is a completely different beast. They're distinct regions of the country, and your experience totally depends on where you go. You really need to think through what kind of trip you want before you start booking anything. For example, if you wanna hit the two most popular tourist destinations, Manuel Antonio and La Fortuna, you're looking at a minimum of 11 hours of driving over the course of your trip. Add in traffic, poor road conditions, motion sickness stops, or the fact that you need to arrive before dark because lots of routes don't have great lighting... You could stretch that drive time by several hours. And sunset in Costa Rica is at 6:00 PM so you have to work backward from there. Another example is the OSA Peninsula down in the south. It has some of the best wildlife viewing in the entire country. I really wanna go someday, and I've already picked out where I'm gonna stay, but if you're driving there, it's a minimum of a six and a half hour trip, and often it can go longer than that. Most people who drive to Osa spend the night somewhere on the way there, and again on the way back. That's basically your entire trip if you have a typical vacation schedule. If you want nice beaches and reliably dry, sunny weather, your best bet is Guanacaste in the northwest corner. It is close to the airport in Liberia, but not really anything else. You could also fly between regions in Costa Rica on Sansa Airlines. They run small planes, let's say six to 20 passengers at a hundred to$150 each way. You'll have to think about strict size and weight limits on your luggage, but if you're comfortable in the small plane and it fits your budget, it could save you a lot of driving. In Hawaii, you can hop between islands with a quick and often cheap flight On Southwest or Mokulele. We've grabbed inter island flights on Southwest for$59 and we've used our companion passes. The logistics are a lot simpler, the prices a lot lower, and it's a full-size plane, which I know a lot of people are more comfortable. You can also usually fly back to the mainland from whichever island you end up on. But in Costa Rica, if you're using small planes to get around, then you might have to take a round trip flight to get back to an international airport. For our Costa Rica spring break trip, we did eight nights and structured it as the Central Valley, then La Fortuna, and finally the Papagayo Peninsula In Guanacaste. It worked really well because it was just the four of us, but with a big group or people who aren't awesome in the car, we'd definitely opt for a more focused itinerary- fewer stops, less time on the road, and that can be limiting depending on what you wanna do. One more thing on logistics. Costa Rica requires much more careful planning. And because popular properties have fewer rooms, you really do need to book early. I started all of this research 10 months in advance, and some of the properties I was looking at were already showing limited options. Hawaii has so much more capacity. You have more flexibility in Hawaii, though booking early is still smart for award availability. So in terms of logistics, Hawaii is definitely an easier trip to plan and execute. Let's talk seasons now. Both of these are technically year-round destinations, but there's some nuance in when to go and where. Hawaii's a little more intuitive. Summer is warm and dry across the islands. Winter is still nice, but the eastern and northern sides of each island, the windward coasts, can get cool, rainy, and the ocean swells can be dangerous. The leeward sides, it's the west and the south, are more reliably pleasant in the winter. The good news is that Hawaii's islands are small enough that if you hit bad weather, you can usually drive an hour to find sunshine, and then you get to turn around and see a rainbow. That part is pretty great. Of course, as I'm recording this, plenty of families are redirecting their spring break trips to Hawaii because of a huge incoming storm system, but just know that that's not typical. Costa Rica requires a bit more homework. The two main seasons are the dry season, December through April, and green season May through November. January and February are usually the most pleasant times to visit. They're dry, but not as hot as March and April can get. September and October are the wettest, outside of the Caribbean coast. In fact, some hotels down in Osa literally close for that part of the year because it's just too rainy for anybody to come. But the Caribbean side of Costa Rica plays by its own rules. It actually gets some of its driest weather when the Pacific side is getting hammered in the fall. And your elevation matters too. The mountains near Manuel Antonio can get a bit of rain even in the dry season. Here's the important difference from Hawaii, though Costa Rica's terrain and road conditions make it hard to just escape bad weather on the fly. Once you're in a region, you're probably gonna be staying there for a few days. So picking the right area for the time of year you're visiting really matters in Costa Rica. Finally, let's talk about accessibility. This is a topic I've started paying a lot more attention to over the last few years because we travel with my mother-in-law pretty often now. She still loves to get out and explore. She has a real zest for seeing the world, but she moves more slowly and carefully than she used to and stairs can be a real challenge. Based on my research and our real world experiences. Hawaii is significantly more accessible than Costa Rica for travelers with mobility challenges. That's not a knock on Costa Rica, it's just the reality of how things are built there. In Costa Rica, a lot of the nicest properties are built into hillsides and feature individual bungalows or multiple buildings connected by paths with stairs. At a lot of the most beautiful resorts that's just how it works. Like at the Andaz Papagayo, the main beach requires going down and obviously later back up some really substantial stairs. There are no guest elevators on the entire property. management told me that they do their best to assign ground floor rooms to people who need them. And of course, there's golf cart transportation to get around the main areas of the property. But it's not seamless. The design philosophy in Costa Rica is that building should be in harmony with the landscape rather than dominating it. And honestly, I respect that. In fact, when it's just our immediate family, I love it. I'd much rather see low buildings tucked into the treetops instead of massive towers blocking the view like you sometimes find in Hawaii. But it definitely creates challenges for people who need smooth, flat, predictable paths or elevators to get around. Now, there are some accessible properties, but like most places in Costa Rica, they're on the smaller side. If you aren't booking way in advance, you might miss out on them entirely. In Hawaii, there are plenty of large resorts and condo complexes with excellent accessibility features and lots of capacity. If accessibility is a priority for someone in your group, Hawaii is the much easier choice, especially if you're planning at the last minute. Okay. You've been really patient and I promised I'd tell you what we decided for our winter break trip. Ready. Drum roll please. We're going to Costa Rica. I know it didn't sound like that was gonna be the right choice, but for a group of 12 to 14 people, the cost savings were just too significant to ignore. I'm talking about a three bedroom ocean view condo at 60% less than a one bedroom in Maui. That math is hard to argue with when you're multiplying it across a large group and you need three or four condos. The flights from Columbus and Chicago work better for Costa Rica too, which means more days on the ground. The travel will be a little worse for the part of the family coming from Los Angeles, but not enough that it makes a huge difference. We'll have 10 days in country versus the nine we'd get from Hawaii, given the longer travel and bigger time change. And it was really, really, really hard but eventually I did find properties that should work for grandma. It took a lot more effort than it would've in Hawaii, I'm not gonna lie. And there were a few times that I almost gave up, but we got there eventually. Now, here's the honest truth. There's no wrong answer between these two destinations. Hawaii is genuinely one of my favorite places in the world, and I know we'll go back. When we do, it's gonna feel like coming home. The right choice really comes down to your family's priorities. If budget's your main concern, especially coming from the East Coast or Midwest, costa Rica probably wins. If you have little kids, hawaii is easier in almost every way, and you could save Costa Rica for when they're older. If accessibility is the most important thing for someone in your group, Hawaii is significantly easier to navigate. If you want adventure, wildlife, and experiences that you just can't get anywhere else, Costa Rica delivers. So that's it for today's episode. I know I loaded you with a ton of info, but I hope it helps you figure out which destination's right for your family. If you have questions about either place, head to thefamilyvoyage.com and leave a comment or hit me up at the family voyage on Instagram or Facebook. I genuinely love helping families work through these decisions. While you're here, hit follow so you don't miss what's coming up. And if you have a minute to leave a five star review, it makes a real difference in helping other families find the show. I'll see you next time on Family Travel unpacked. Safe travels!