Travel with Kids / One Family’s Surfing Road Trip from California to Costa Rica

travel with kids
The Williams Family – Rob, Cheryl, Kirra and Kai

Talking to people about travel with kids can be a funny thing. It seems like almost every time I mention going on surf trips, lengthy vacations, or the idea of taking a year off to travel the world, I get a common response along the lines of, “Well you better do that kind of stuff now before you have kids, because once you have them you won’t be able to.”

It’s interesting that people make these kinds of statements like it’s the absolute truth, an undeniable fact of life. And while my wife and I don’t have children and therefore can’t speak from firsthand experience, we’ve heard of these mystical people who travel with kids, go on “crazy” trips, and say yes to a life of adventure.

Recently, we met Rob and Cheryl Williams– teachers, surfers, and very cool parents of a thirteen year old daughter (Kirra) and ten year old son (Kai). In 2014, Rob and Cheryl fulfilled their dream road trip and drove from San Diego, California through Mexico and Central America to the beautiful land of pura vida, Costa Rica. In a van, with their two kids and a lab named Buddy.

travel with kids
Rule of the road – don’t take yourself too seriously

We were pretty inspired by this epic family adventure, so we met up with Cheryl and Rob to pick their brains and tap into the perspective, wisdom, and experience that comes along with taking a year off and driving 3,300 miles down the coast with the whole family in tow.


What inspired you to take the trip?

Rob: We’ve always wanted to go. Growing up traveling, surfing, learning Spanish and wanting to explore that whole region south of the border. We’d been thinking about it for a long time.

travel with kids


How long did it take to drive from San Diego to Costa Rica?

Rob: We initially planned for about two months and it all worked out according to plan. We left in July 2014 and got there by September.


So did you guys just stop and surf all along the way?

Rob: We took the coast roads pretty much the whole way. We didn’t hit too many super secret spots though. Since we were traveling with kids we decided to keep it simple and hug the coastline and hit all the best spots.

Cheryl: Mexico was great because they catered to travelers and campers, and there’s a whole subculture of travelers so it was very accessible in terms of camping and RV parks, and it felt plenty safe the whole way.

travel with kids

travel with kids
Kirra and Kai’s first wave together


There’s quite a bit of negative press about Mexico. Did you have any concerns about driving through?

Rob: I always knew that it would be okay. Cheryl was doing lots of research and planning. I was just ready to go…

Cheryl: I was like okay, let me look at a map, let me have a tentative route. And that’s when I kind of started doing my research and found some blogs that I started following. There’s one in particular called Neli’s Big Adventure, and it happens to be a couple from LA. They had been traveling for almost a year and went all the way down to Panama and their blog is told from their dog’s point of view.

Rob: Their blog was perfect for us because they listed all the dog friendly campsites, and super cheap accommodations. You could just show up in your camper and pay a tiny bit of money to plug into power. So we found a lot of really nice places… It’s pretty funny actually, while we were in Guatemala Cheryl was looking at their blog and saw they were on their return trip, saying they were up at beautiful Lake Atitlan. And we were like “that’s where we are right now!” So we actually reached out and took a water taxi across the lake to go meet them. Yeah, it was great, we got to hang out with them and meet their dog Neli… We told them we had been following their blog the whole time, they had such great information about crossing borders and all that stuff.

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The Williams Family with the Neli’s Big Adventure Crew


What was it like crossing borders with your dog?

Rob: Crossing borders with a dog is just a whole extra pain. They make you fill out more paperwork, and of course make you pay a little bit more money. You have to go through live stock, agricultural checks, and what not.

Cheryl: It’s a little bit of an extra hassle, but you know… We didn’t have to quarantine or anything like that, so that was nice. Just turning in the extra paperwork.

Rob: Yeah borders suck.

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What were some of your favorite spots on the way down?

Rob: I’m just going to name all the surf spots. Scorpion Bay was the first stop and was knee-high perfection. It was such an epic way to kick off the trip, and was perfect for the kids. We camped in the van for the first official night and it was hilarious. Right as we were going to sleep, we noticed Kai had a giant bug like the size of my hand laying across his face… I smacked it off.

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Cheryl and Kai at Scorpion Bay

Cheryl: I really liked Rio Nexpa, that place was very cool. This little bay with a left point break. Ticla was one of our first surf spots that we went to.

Rob: Just south of Mazatlan a little ways… Barra de la Cruz. We stayed at Pepe’s Surf Camp and met some really cool travelers. It was awesome to just hang out with everyone. The waves were small, but they were perfect for the kids.

Cheryl: Sayulita. And Playa de San Diego too, a long right point break. We were trying to drive down to Salina de la Cruz and got stuck in a mob of people at the border who were protesting.

Rob: That’s where my cousin lives on a sailboat.

Cheryl: Melaque.

Rob: Yeah, that was non-surfing but the most beautiful little bay and we had a good set up. Camped right on the beach.

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Pick up soccer game in Melaque

Cheryl: The kids played in a pick up soccer game. The sunsets were just epic. Some of the surf places we went to, Ticla in particular, in the afternoon all the locals came in and they had these big nets and they were catching tiny fish. Just watching it all was so great. 

Rob: Jiquilillo. That was in Nicaragua. We scored a head high plus, super peaky, really glassy magical session in the late afternoon, it was amazing. And El Zonte, in El Salvador, it’s a super epic right point break. It was too big for the kids though. But I surfed everyday, all day, and scored so many incredible sessions. And of course we stopped at Popoyo in Nicaragua.

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El Zonte, El Salvador


Were you ever in any moments when you were like “oh, shit?”

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A little car trouble? No problemo, there was plenty of friendly help in town

Rob: Only slightly. Everyone we encountered was generally genuine and good. We didn’t ever feel threatened or concerned. I think when you’re traveling as a family and with kids people are extra nice and welcoming.

Cheryl: I think as a mom, I felt more of that the entire trip because…well, I’m a mom! (laughs). And you’re always kind of worrying. But Rob is really good with that. His outlook is like, we’re good, and if something happens, then we’ll deal with it. So he definitely put my worries at ease. And I tried not to think about it too much… I was talking myself through that most of the drive so I could really be present and enjoy it.

Because you could spend the whole time not enjoying it, or you could be present living in the moment, and just enjoy the whole wonder and excitement of it, and the fear, all of that. That’s just a part of traveling. Just really embracing it all and also I was reflective that if I showed fear to my kids then they would be like, “Oh no, mom’s scared so I’m scared!” So I just had to relax and keep moving forward.

More in the beginning when we had just left, the kids were like, “I don’t know, we could get kidnapped… all these bad things could happen.”  And we were like, yeah it could, but it could happen here in the United States. If you go into a wrong neighborhood, or you’re in the wrong place at the wrong time. That could happen anywhere. So you put your faith in God and just go and enjoy it.

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The winding road to Lake Atitlan in Guatemala

Rob: We did have a nightmare situation happen to us in Nicaragua. Our daughter got appendicitis.

* Long story short, Rob and Cheryl got Kirra to the hospital. It was pretty rough–Kirra had to undergo surgery in Managua, but thank goodness she recovered and got through it like a trooper. Needless to say it was quite the experience, and it gave the Williams family a new appreciation for the amenities we have here in the US.  


How did your kids acclimate in the beginning of the trip?

travel with kids

Rob: Our son had no problem. He could be on the road just surfing and living in the jungle easily, no problem at all, he loved it.

travel with kids

travel with kids

travel with kids

Cheryl: Our eleven year old daughter had a harder time with it. Just being away from her friends at school and being at a tricky age.

Rob: It was tough for our daughter at first, being all on top of each other in our van and then in our little place once we settled down. She was in seventh grade thinking she’s missing out on everything back home. She thought we were the worst parents in the world for a little while.

Cheryl: Yeah, that was difficult. But generally speaking our kids loved the trip. The hardest thing for them was sitting on the same seat on the couch in the van. But having to stop at random places, eat new foods, see new things everyday, their eyes and their souls were wide open and they just took it all in. And now that we’re back, they’re so grateful of the trip and have definitely got the travel bug. They’re so glad we went.

travel with kids

travel with kids

travel with kids

Rob: We’ve always been a big road trip family so they’ve traveled a lot, so they handled that part really well. I think it took our daughter and Cheryl a little while to slow down and get settled into Costa Rica.

Cheryl: I’ve always had multiple jobs; college, teaching career, wearing so many hats in life, being a wife and a mom. I had to hit the emergency brakes and tell myself “Okay, you don’t have to do anything or feel guilty about it. You could be relaxed, you don’t have to be in charge of everybody.”

Rob: She was stressing about the kids and stuff, but I was like they’ll be fine.

Cheryl: Fortunately our kids are good students. We didn’t struggle to keep up with their education. The experience itself was education enough, we made sure they wrote in their journals every day. We tried to do the home school thing, but Rob kept reassuring me not to worry about it. The first couple of months we were trying to be structured. Rob’s like “we’re on vacation” and I finally just decided to let go. That was a big moment of growth for me. I slowed down and got into yoga, music, health, relaxation, and on a journey to spiritual wellness. It was all about finding balance.

travel with kids

travel with kids
Paddle board yoga anyone?


What was your daily routine like?

Rob: There would be howler monkeys making noise at 5:30 in the morning, and I’d just usually get up by myself first and head down to the beach to get in a surf session and work my way back. I’d get home at 7 or 8am, make some coffee, fresh fruit smoothies, and breakfast. Then everyone would head down to the beach and surf for like 3 hours, then head back and have lunch and work on the property and maybe do some school or art and what not. Definitely did a lot of work on the property… And then we would go back and get in another surf session in the afternoon again.

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Rob hacking away on the property


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Heading to the beach… again

Cheryl: Haha, we definitely were on vacation and we’re paying for it a bit now. But in the end we got really good quality time together, not distracted by anything.

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Quality family and friends time at Lake Atitlan, Guatemala

Rob: Then we’d go back out for sunset. It was awesome… I’d grab the machete and go chop through the trees on our lot, the kids would go build forts or go to the neighbors for wi-fi, it was all so fun.

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A day in the life of Rob, yet another sunset session


How long were you in Costa Rica?

Rob: We were gone like 14 months altogether. Two months to get down there, ten months actually in Costa Rica, and then a couple months catching up with family in Colorado and what not afterwards.

Cheryl: Yeah, it was nice to have a couple months re-acclimating into society.

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Cheryl and some legit coconut water


Did you drive back?

Rob: No, we left the van there. Our property is a one minute dirt bike ride from the nearest break. We bought it 15 years ago for pretty cheap. It’s a perfect family neighborhood, peaceful and quite, a real cool tight knit community. The beach itself is all mangroves, there’s only one restaurant.

travel with kids

travel with kids


Did you have phones?

Rob: We used a basic flip phone for emergencies and for having friends’ numbers. We’d just buy minutes at the grocery store as needed.


So what’s next? Are you planning to go again?

Rob: We have plans to go back and forth until the kids are in college. We could do it right now, but we want or kids to have the same education and opportunities that we had growing up.

Rob: Yeah, I could go right now and could just live in the jungle and be a surf bum… But I don’t want to force my choices and lifestyle on them.

travel with kids


What did your kids think about the trip in the end?

Cheryl: It was very cool hearing it from our daughter. Towards the end of our trip she was thanking us for taking them; she loves Costa Rica, surfing, nature, and the simple life. She can’t wait to go travel the world and go on surf trips with her friends.

travel with kids


What was the hardest thing about coming back?

Rob: Don’t even get me started, I can’t even do it. I want to go back so bad.

Cheryl: We had a nice re-acclimation period to adjust to the faster pace of life.

Rob: The hardest thing for me is my surf trunks that I wore down there I can’t even fit into anymore. We were so fit, surfing like 5 hours a day.

Cheryl: Yeah, we ate fresh fish and sushi every day, and slept so good. We’d go to bed at dark and wake up to the birds and howler monkeys in the morning.

travel with kids

Rob: I surfed in one week down there as much as I’ve surfed since we’ve been back. It’s almost been a year! And everyone is all mean and aggro in the lineup here compared to the vibes in the water down there, you just have to get in your own zone. And it’s cold.

travel with kids


How did your family, friends, and people in general react when you shared your plans with them?

Rob: 90% of people said don’t do it, you guys are crazy. A lot of people are gonna tell you you’re crazy. My parents were all about it though; they were always big on traveling.


What advice do you have for parents considering an extended family trip?

Cheryl: It’s definitely something that I would highly recommend after taking the experience with my kids and my family. Just plan the trip with your family and make it happen. Even if it’s just for a week, a month, or however long you can afford to go. Go somewhere you’ve never been. Find a place in the world that you’d like to go, get your kids’ input, and do some research as far as what the culture is like. Ask yourself questions like: How can I be involved in the community, participate in rituals, traditions, and festivals, etc?

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Cheryl getting involved with the local community and debriefing for their beach event

Don’t just hang out in your hotel. Do your research, anything is possible! What’s amazing is that there are so many travelers, so many families, so many couples out there doing it, people who are experiencing life and what the world has to offer, and what other cultures have to offer because they just chose to. Like anywhere, things are going to happen. You’re not always guaranteed your day is going to go as planned, and why limit yourself from what’s out there if you don’t decide to go?

travel with kids

Rob: Do you mean as far as keeping them safe and what not? Some people will just never go. But like Cheryl said and for her too, just researching and reading blogs and mapping things out is a good start. Getting the trip on paper and a rough plan visually in her mind really helped her a lot. I guess people would just have to look into it if it is something that they want to do. For me, I was just ready to pack our bags and the car and get south of the border and figure it out as we go. It helps that I speak Spanish but I believe that people are pretty much genuine and kind for the most part everywhere you go. 

travel with kids

People need to just travel with some common sense. Don’t put yourself in sketchy areas doing sketchy things. Stay away from traveling around at night and in bad parts of town. We met so many girls traveling around solo, being smart about it and they were doing just fine. And in our experience, people everywhere we went embraced and looked after kids. So kids could be your biggest asset in a way, because people tend to gravitate towards them and take you in. And people are generally good and mean well.

travel with kids


So there you have it! It might not be for everyone, but gosh darn it we have proof that you can travel with kids–even in a van through Central America.


travel with kids

In addition to being super cool parents and adventurers, Rob and Cheryl are the founders of The Shine Project Foundation, an organization focused on bridging the gap between local communities and families with children with special needs. While they were in Costa Rica they coordinated an awesome event for local kids, and they just had their second beach fun day event back home in Encinitas.

To learn more about The Shine Project Foundation or volunteer for an upcoming event, visit their website.

travel with kids

A huge thanks to Rob and Cheryl for sharing their family travel wisdom!

Here’s a few more sweet sweet surf pics for your viewing pleasure… 🙂

travel with kids


travel with kids
Rob at Ollie’s Point


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Kai at Ollie’s Point


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travel with kids
Kirra on a nice one!


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Playa Negra


travel with kids


We hope this has inspired you to start planning the trip of your dreams! Leave a comment and let us know what they are!

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9 thoughts on “Travel with Kids / One Family’s Surfing Road Trip from California to Costa Rica”

  1. Amazing and Inspiring story! I’m preparing to have kids soon and start a family of my own, but I’m nervous because I love traveling so much and want to get as much in before I have kids. This was truly inspiring as something I’d like to do with my husband.. and soon to be family that traveling- and long destination surf/road trips are totally possible with children. Thank you so much for sharing! I’d love to follow Cheryl’s personal blog or story if she has one. She’s an inspiration mom for sure!

    • Thanks for sharing your thoughts, Jen! We agree, the Williams’ family trip is super inspiring and an awesome example of the great surf travel adventures to be had with a family (and dog!) in tow.

  2. Hey really great piece. My family hasn’t pulled the plug on our real lives yet, but it’s something I’ve wanted to do since before we became parents. Now that our girls are getting to the right age, I’m stepping up my planning. These folks are super brave! I’m not confident enough to drive through Mex. New Zealand is on my list. I also am interested in Sri Lanka and other parts of Indonesia, though the terrorism threat seems pretty real. Thanks for an inspiring story!

  3. Amazing adventure! You are very brave for a long journey. Absolutely fantastic, I can not necessarily do that. Did not you want to come to Bali and try adventurous there? And we have schools that also gives surfers adventure to a few places. That is very fun. Gain experience and the ride was very amazing! Check this site and make sure you get a better experience.

  4. Unbelievable! What an awesome story. Good on ya for dropping in big and taking on this challenge and trip of a lifetime. What a wonderful experience for all of you. Thanks for sharing, for having the guts to do it, and giving back to the communities and lives you touched along the way.

  5. What a trip! Congrats on your adventures! Our crew is headed to Costa next month from North Florida- thanks for the insight. It’s a big leap for us and our three kids, but here we go… ✌?️


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