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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Showing 1-24 of 143 results
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 ...
“HOLD ON FOR DEAR LIFE!” 🌊😂
“HOLD ON FOR DEAR LIFE!” 🌊😂 Followed immediately by me laughing like an absolute maniac… All we were trying to do was go to the STORE. 😂 When you live on a boat, even a simple grocery run can turn into an adventure. Windy day + bumpy seas + dinghy = apparently the funniest thing I've experie...
We Followed Him Through the Boulders… 😳🏝️
Every time we thought we'd reached the end of The Baths… there was another passage to explore. 🤯 This time we're following Ashton through the sand, between enormous granite boulders, and deeper into one of the coolest places we've explored in the BVI. Around every corner: another li...
We Almost Quit Sailing
What was supposed to be a manageable overnight sail from the USVIs to St. Martin turned into one of the hardest passages we’ve experienced as a sailing family. The forecast said one thing. The ocean gave us something completely different. We found ourselves beating directly into the wind and waves...
There’s a BEACH Under These Giant Boulders?! 🤯
Just when we thought The Baths couldn't get any cooler… we found ourselves walking through soft sand UNDER these massive granite boulders. 🤯 Sunlight sneaking through the rocks, little pools of water, sand beneath our feet—it honestly feels like you're exploring another world. The Baths ...
Okay… Now We Actually Have to Get DOWN 😳🪨
Getting through the boulders was one thing… Now we actually had to climb DOWN them. 😳🪨 Exploring The Baths in Virgin Gorda, BVI definitely isn't your average beach day. Between the ladders, giant granite boulders, tight spaces and scrambling, getting there is half the adventure. And of cours...
Wait… THIS Is the Trail?! 😳🪨
Wait… THIS is the trail?! 😳🪨 Exploring The Baths in the British Virgin Islands meant climbing, squeezing, ducking and scrambling our way through massive granite boulders. Definitely not your average walk to the beach. 😂 And somehow, the kids make it look WAY easier than the adults. Would you cli...
Apparently We Have a New Crew Member… 😂🪿⛵
Apparently *Isla* has a new crew member. 😂 This pelican landed on our dolphin seat, got comfortable, and basically decided he lived here now. No rent. No chores. Just oceanfront accommodations and unlimited fishing. Honestly, he's got a pretty good setup. 😂🐟⛵ What should we name him? #Pelic...
POV: Your Kids Get to Call This Childhood 🥹⛵️
Somewhere along the way, this became normal to them. 🥹 Barefoot. Salty. Piled together on the trampoline with nothing but ocean ahead. We traded the “normal” life for more time together, more adventure, and a childhood we hope they’ll never forget. 🤍⛵️ Would you raise your kids on a boat? #Saili...
Boat Life Will Teach You Skills You Never Asked For 😂⛵
Things I never expected to learn when we decided to live on a sailboat: how to make our own cushions. 😂🧵 Boat life has a funny way of turning you into a mechanic, electrician, plumber, seamstress… or at least making you attempt all of the above. Today I’m on the dock learning one more skill to add...
This Is What Recess Looks Like When You Homeschool 🌎❤️
This is what recess looks like when you homeschool. 🌿💦 A river fed by a waterfall, a jungle to explore, and plenty of room to just be kids. We’ve been homeschooling for three years now, and while there are still books, assignments, and plenty of normal school days, some of our favorite lessons hap...
15 Years Apart… and THIS Is Their Relationship 🥹❤️
Brotherly love ❤️ Ashton and Lily swing dancing together in the salon aboard Isla is one of those little moments I never want to forget. We share a lot of big adventures here—but sometimes the smallest moments become the best memories. #SiblingLove #BigBrother #LittleSister #FamilyMoments #BoatLif...
When You Live on a Boat… You Improvise 😂🥊
No punching bag? No problem. 😂🥊 Tie a pillow to the halyard and apparently you’ve got yourself a full boat-kid boxing gym. Living aboard means getting creative with what you have—and Miles definitely understood the assignment. 😂 Would you call this genius… or peak boat-kid behavior? #BoatLife #B...
His Confidence Is UNMATCHED 😂🎣
Nobody hypes Miles up quite like… Miles. 😂🎣 He hooked a fish and immediately became his own personal coach. The confidence, the commentary, the celebration—this kid cracks us up. Fishing has become such a huge part of our life aboard Isla, but honestly, the personalities behind the catches are usu...
Our Kids Think This Is a Normal Swing… 😳⛵
Most kids have a swing set… ours have a bosun’s chair and a halyard. 😂⛵ Lily loves getting hoisted up the rigging just for fun, swinging above the boat like it’s the most normal thing in the world. Living aboard has definitely changed our kids’ definition of a playground. 🌊 Would your kids LOVE t...