Finding Our Isla Sailing
We’re a family of five who left traditional life and moved full-time onto our sailboat, Isla. This channel shares the real side of family boat life. What it actually costs, how we homeschool while traveling, the challenges no one talks about, and the moments that make it all worth it. We live aboard full-time in the Caribbean and document life afloat with kids: • the finances behind this lifestyle • daily routines and homeschooling on the water • the hard days, the growth, and the joy • choosing time, connection, and freedom over stuff No highlight reels (okay... maybe a few) No pretending it’s perfect. Just honest life on the water. If you’ve ever wondered what it takes to make a big life change... or you’re dreaming of a different way to live, you’re in the right place. 🌊 Full sails. Full hearts. Full-time family life.
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Finding Our Isla Sailing Latest Episode
We’re a family of five who left traditional life and moved full-time onto our sailboat, Isla.
This channel shares the real side of family boat life. What it actually costs, how we homeschool while traveling, the challenges no one talks about, and the moments that make it all worth it.
We live aboard full-time in the Caribbean and document life afloat with kids:
• the finances behind this lifestyle
• daily routines and homeschooling on the water
• the hard days, the growth, and the joy
• choosing time, connection, and freedom over stuff
No highlight reels (okay... maybe a few)
No pretending it’s perfect.
Just honest life on the water.
If you’ve ever wondered what it takes to make a big life change... or you’re dreaming of a different way to live, you’re in the right place.
🌊 Full sails. Full hearts. Full-time family life.
Finding Our Isla Sailing Journey and Videos Locations
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Watch Finding Our Isla Sailing's Latest Videos
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Showing 1-24 of 166 results
We Tore Apart Our Floating Home!
We finally got our sailboat back in the water… so WHY are we already tearing apart our floating home?! 😳⛵ Just when we thought we were getting closer to sailing away, the projects aboard Isla started piling up! Kasey's tearing into the floors, I'm learning how to sew brand-new exterior cu...
When Your Big Brother Has Your Back… 🥹❤️
Sometimes it's the smallest moments that mean the most. ❤️ While exploring the zoo, Miles couldn't quite see everything, so Krew stepped in and lifted him up for a better view. No big production. Just a big brother looking out for his little brother. 🥹 Of all the incredible things our k...
“There’s a Stray GOAT Over There…” 😂🐐
Just Miles enjoying his ice cream when suddenly… “There's a stray goat over there.” 🐐😂 No explanation. No context. Just a very important announcement in the middle of his ice cream break. Life with this kid is never boring. 🤣❤️ Please tell me your kids say completely random things like this...
He Calls This PARKOUR… 😂
Miles has apparently taken up parkour. 😂 Is it technically parkour? Debatable. Is he having the time of his life? Absolutely! 🤣 One thing about this kid… he's never short on confidence or entertainment. And we wouldn't have it any other way. ❤️ #Parkour #FunnyKids #BoatKids #FamilyAdv...
Even Flamingos Have a Love Life! 😂🦩❤️
Well, apparently love is in the air! 😂🦩❤️ Are these two adorable or what?! 🥹💕 #Flamingos #FlamingoLove #CuteAnimals #Birds #Wildlife #AnimalShorts #NatureLovers #FamilyAdventure #FindingOurIsla #TravelShorts
These Birds Were NOT Shy! 😂🐦
Apparently we made a few new friends today… and they were HUNGRY! 😂🐦 One of the things we love most about traveling as a family is getting to experience wildlife up close. Sometimes the simplest little moments turn into the best memories. These guys definitely weren't shy! Are you a bird per...
We Had NO IDEA What Was Ahead… 🌴👀
Some families go for a walk around the neighborhood… we somehow end up wandering through the jungle. 😂🌴 You never quite know what you'll discover when you head off exploring! #JungleAdventure #FamilyAdventure #TravelWithKids #SailingFamily #Worldschooling #BoatLife #FindingOurIsla #AdventureK...
Would YOU Cross This Bridge?! 😳🌴
Exploring the jungle sounded like a great idea… until we came across THIS rope bridge! 😳🌴 There's something about walking across a suspended bridge surrounded by jungle that makes you question just how adventurous you really are. 😂 One of our favorite things about traveling as a family is dis...
The Hardest Part of Living in Paradise
Living in paradise sounds like a dream… until it's time to get your boat ready to actually enjoy it! 😂⛵ After spending the summer back in Idaho, our family is finally back in Grenada and ready to kick off Season 2 aboard our Lagoon 450 catamaran, Isla! But before we can return to the beautifu...
Are we making a MISTAKE?
After spending our first season sailing the Caribbean as a family, we returned home to Idaho... and suddenly, going back to boat life didn't feel quite as simple as we thought it would. Being home meant family, friends, mountains, camping, birthdays, Yellowstone, and everything we had left beh...
We Didn’t Know If We’d Ever Sail Again
After our first year of sailing the Caribbean as a family, we sailed our Lagoon 450 south to Grenada to haul her out for hurricane season. But as we prepared to leave our floating home behind, we honestly didn’t know if we’d ever come back. Our final sail takes us from Martinique past the incredibl...
“Somebody Forgot to Fill the Gas Up…” 😂
“Somebody forgot to fill the gas up…” 😂 Thank you, Lily, for the status update. We were supposed to take the dinghy into town. Slight problem: no gas. So the boys got to work rowing us to shore so we could find fuel and THEN continue our trip. Nothing turns a simple trip to town into an adventure...
We Found the WILDEST Island in the Caribbean
We thought we knew what Caribbean adventure looked like… then we got to Dominica. This island completely blew us away. We chased waterfalls through the rainforest, swam beneath one of them, explored the famous Indian River, stepped into a filming location from Pirates of the Caribbean, and somehow ...
Morning Coffee Hits Different Out Here ☕️⛵
Morning coffee while Isla sails along… then I pan over and find Lily living her absolute best life on the nets. ☕️⛵️😂 Some days aboard are chaotic. Some are filled with boat projects. And then there are mornings like this. ❤️ I don't think this view will ever get old. #BoatLife #SailingFami...
Imagine Waking Up to THIS… 🌊❤️
Some mornings don't need much of a caption. 🌊❤️ Calm water. A quiet anchorage. Everyone still waking up aboard Isla. Three years into this adventure, and mornings like this still make us stop and appreciate where we get to call home. Could you wake up here every day? #BoatLife #Liveaboard #...
Most Kids His Age Aren’t Doing This… ⛵😳
Miles has spent years learning that everyone has a job when it’s time to sail. ⛵ Today he's helping pull out the genoa while we get Isla underway. One of my favorite parts of raising our kids this way isn't just the places they get to see—it's watching them learn real skills, take r...
Boat Life Still Requires Iced Coffee 😂☕️
Living on a sailboat changes a lot of things… Iced coffee is NOT one of them. 😂☕️⛵ Just another delivery from the onboard mom café. #BoatLife #IcedCoffee #SailingFamily #Liveaboard #BoatKids #SailingLife #FindingOurIsla #FamilyAdventure #LifeAtSea
Our Gym Has the BEST Cool Down 🌊😂
Our Monday, Wednesday, Friday workout routine comes with a pretty great reward. 😂🌊 Workout on the boat. Get hot and sweaty. Then everybody jumps straight into the ocean. I'm not sure we could ever go back to a normal gym after this. ❤️ Would this motivate you to work out? #BoatLife #Sailing...
He Was NOT Giving Up 😂🦀
Apparently we went crab fishing. 😂🦀 This little guy spotted the food on our hook and was DETERMINED to get it. Watching those tiny claws try to hang on might be way more entertaining than actually fishing. 😂 Are you rooting for the crab or us? 👇 #Crab #Fishing #BoatLife #OceanLife #SailingFamily...
Eastern Caribbean Was NOT What We Expected
This was NOT the Caribbean we expected. Sailing south through the Eastern Caribbean brought us to Guadeloupe—and what we found completely surprised us. After leaving St. Kitts and Nevis and making a quick stop in Montserrat, we sailed Isla into Deshaies, Guadeloupe, ready to get off the boat and e...
Our Ride Home Looks a Little Different… 🌅⛵
There's something pretty special about heading home at sunset… when home is floating somewhere out there. 🌅⛵ All five of us piled into the dinghy, salty, tired and watching the sky change colors as we made our way back to Isla. Three years into this adventure, and moments like this still don&...
I Was SO Confident Too… 😂
I was SO confident. 😂 Kasey was looking for fuel stabilizer, and I was positive he was digging through the cleaning supplies. “It's not in there.” Narrator: It was, in fact, in there. 🤦♀️😂 Living on a boat means knowing exactly where everything is stored… until apparently you don't. ...
We Went Up to FIX Something… Then Broke THIS 😳⛵
Nothing is ever just ONE project on a sailboat. 😂⛵ Ashton headed up the mast to inspect the rigging and make sure everything looked good. Then, because apparently the boat felt like our project list wasn't long enough… we broke the electric winch. 🤦♀️ Boat project math: 1 thing to check + ...