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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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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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 + ...
Nobody Taught Her to Hike Like This 😂
When the trail turns into one giant muddy slide… you improvise. 😂 Lily decided the safest strategy was to straddle it and bounce her way down the mountain one side at a time. Honestly? Can't argue with the technique. 😂 Life with this girl is NEVER boring. Would you call this hiking… or cont...
One of Our Worst Nights at Sea 🌊
“That was terrible.” After a long night of getting tossed around at sea, I think Kasey's face pretty much said it all. 🌊😳 The forecast hadn't prepared us for what we experienced, and by morning we were exhausted and VERY ready for this night sail to be over. Sailing isn't always su...
Our Family Car Doesn’t Have Wheels 😂
Just a normal family car ride… except our “car” is a dinghy and the road has WAVES. 😂🌊 Everyone bouncing around, hanging on and somehow still having the best time. After living aboard, I'm pretty sure our kids have completely forgotten what a normal commute looks like. 😂 Would your family LO...
Would YOU Go This High on a Sailboat?! 😳⛵
That's Ashton… at the TOP of our mast. 😳⛵ When you live on a sailboat, sometimes somebody has to go up—and apparently Ashton drew the short straw. 😂 The view might be incredible, but I'm perfectly happy watching from down here. Would you go to the top? #Sailing #BoatLife #Sailboat #Sai...
Our 5 YEAR OLD did…
She’s FIVE. 😂🌊 Lily put on her snorkel, dove underwater and casually did FOUR flips in a row while holding her breath. Meanwhile, I’m watching from above wondering how she still has air left. 😂 Boat kids really are built differently. How many flips did you count? 👇 #Snorkeling #BoatKids #Underw...
All He Wanted Was My Phone Number… 😂
All he wanted was my phone number… 😂 Fast-forward 29 years and Kasey is walking home from a hike with Lily over one shoulder and a giant bundle of leaves from our sugar plantation tour in the other hand. Pretty sure this isn't what 13-year-old Kasey thought he was signing up for. 😂❤️ But hey...
Our Drinks Don’t Get Much Fresher Than This 🥥🌴
Does it get any fresher than this? 🥥🌴 Fresh coconut water, straight from the coconut, enjoyed aboard our floating home. Sometimes it's the simplest moments that make us stop and think… yep, this life is pretty incredible. ❤️⛵ Coconut water: LOVE IT or leave it? 👇 #BoatLife #IslandLife #Coco...
He Wasn’t So Sure About This… 😂🎣
Catching the fish was exciting… Taking it OFF the hook? Miles wasn't quite as sure about that part. 😂🎣 Thankfully, Nana was right there beside him, showing him what to do and giving him the confidence to try. One of our favorite parts of having Nana and GoGo aboard was watching them teach ou...
This Is What Chores Look Like When You Live on a Boat 😂🌊
Today's chore: clean the bottom of the house. 😂 Except when your house floats, that means grabbing a mask, jumping into the ocean and scrubbing the bottom of the boat. 🌊⛵ Krew definitely has a different chore list than most kids. Would YOUR kid volunteer for this one? 😂 #BoatLife #BoatKids ...