Watch Sailing & Boating Adventures Around the World

Explore sailing, boating, and water sports through our curated video archive. From epic sea voyages to serene diving escapes, discover unforgettable adventures from top YouTube creators. Start your journey. Dream big. Sail far.

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We Found the WILDEST Island in the Caribbean
Finding Our Isla Sailing

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 ...
Eastern Caribbean Was NOT What We Expected
Finding Our Isla Sailing

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...
We Went Up to FIX Something… Then Broke THIS 😳⛵
Finding Our Isla Sailing

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 + ...
We Almost Quit Sailing
Finding Our Isla Sailing

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...
The Greatest Gift My Parents Gave Us Wasn’t a Thing
Finding Our Isla Sailing

The Greatest Gift My Parents Gave Us Wasn’t a Thing

Sometimes the greatest gifts aren't things—they're the lessons and memories that stay with you forever. ❤️ This week aboard Isla, Nana and Gogo join our family to celebrate my 40th birthday, and what started as a family visit became one of our favorite weeks of boat life. We waste no tim...
This Didn’t End the Way We Hoped… 🎣💔
Finding Our Isla Sailing

This Didn’t End the Way We Hoped… 🎣💔

What started as an exciting fight turned into a tough lesson. Krew and I battled a huge barracuda in rough seas, but the hook was swallowed too deeply. We did everything we could to safely release it, but we don’t think it survived. Moments like this remind us that fishing isn’t just about the exc...
Our First Overnight Sail as a Family
Finding Our Isla Sailing

Our First Overnight Sail as a Family

Our first overnight sailing passage took us from St. Martin to the U.S. Virgin Islands aboard our Lagoon 450 catamaran—and honestly, it wasn't what we expected. As a family of six living aboard full-time, sailing through the night with our kids was one of the biggest milestones of our journey....
My Son Had To Retrieve His Spear… While Sharks Circled 😳🦈
Finding Our Isla Sailing

My Son Had To Retrieve His Spear… While Sharks Circled 😳🦈

One of those moments that reminds you we’re visitors in their world. 🦈 Krew speared a fish, but it became lodged in the rocks. Within seconds, two sharks showed up and started circling. We left the water immediately and came back later to retrieve the spear. The sharks were still there. The missi...
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