Watch Sailing & Boating Adventures Around the World tagged “Caribbean”
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.
We explore Sint Maarten starting on the Dutch side — from planes screaming overhead at Maho Beach to cruising the surprisingly affordable liveaboard scene on Simpson Bay Lagoon.
Living aboard here can be way cheaper than you might expect, and the vibe i...
The boat drawing is complete — and we have a winner.
The drawing was done automatically, but the reserve was not met. As promised, that meant the winner would receive the partial cash equivalent of the funds raised rather than the boat itself.
Right af...
WE ARE LEAVING ST MARTIN!!!!! But first - Provisioning Time. Come along and see a full day of shopping for random sh*t you never wanted to spend money on in the first place & we'll tell you how much it costs!
Thank you for all your support!!!
Busines...
We kick things off soaking up the sun at Nikki Beach, easing into another unreal day in Saint Barthélemy. From there it’s poolside vibes, cold drinks, and Yosaira absolutely stealing the show in a tiny bikini that turns heads everywhere we go.
That nig...
Join us as a fun day unfolds in the Bahamas with activities like snorkeling, tubing, and exploring a sunken wreck. The day highlights the joy of family bonding and adventure, concluding with reflections on creating lasting memories and preparing for their ...
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We break FREE from the boatyard AND the lagoon to anchor out in crystal clear waters...FINALLY!!! It's been 13.5 months ON THE HARD and we don't quite have our sea legs yet and we get TOSSED around like rag dolls. But there is still work to be done so we ...
We start the day soaking up French Caribbean vibes at Grand Case, spending the afternoon at the iconic Rainbow Café. From there, we set sail for a short hop over to Anse Marcel, grabbing a marina slip and enjoying a relaxed night onboard.
The next mornin...
We fly to the French side of St. Martin and kick off a brand-new sailing adventure aboard a 50-foot Leopard catamaran with an all-new crew. After provisioning and getting settled, we set sail along the coast toward the iconic anchorage at Grand Case.
Once...
It has been a LOOOOOONG 9490 HOURS IN THE BOATYARD & we are FINALLY ready to SPLASH! In this episode we do the final push to launch !!!!!!!!!!!!
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The journey starts from Nassau Harbor, where the crew prepares the boat and discusses their route. Then we're sailing away! After a stop at Chub Marina for diesel, the crew will share boating experiences. Approaching a remote anchorage, they discover an un...
Our final day in French Polynesia was one to remember. 🌴
We set out on a long hike through the jungle to some incredible waterfalls, soaking up every last bit of this amazing place before it was time to go.
That evening we shared one final night onboar...
We set sail on one of those rare, perfect days in French Polynesia—a slow, easy cruise from Tahaa to Raiatea. No rush, no schedule… just smooth water, warm sun, and island vibes.
We enjoyed lunch underway while Chloe relaxed on deck, soaking it all in...
Let's explore the daily life on a boat, focusing on meal preparation, laundry management, and the challenges of cruising. We'll share family moments and the joy of discovering new places, along with routine tasks like shopping for supplies and ensuring the...
Island hopping around Taha’a in French Polynesia turned into one of our wildest days yet. Chloe was dancing on deck in her bikini as we sailed through crystal-clear lagoons, stopped to tour a local rum distillery, and then headed out to the barrier reef ...
Ever wondered what it’s really like to charter a yacht in the British Virgin Islands? This is the complete experience.
In this full-length sailing movie, I combined all 7 episodes from our BVI charter into one 1.5-hour, start-to-finish journey showing e...
After four unforgettable nights in Bora Bora, it was finally time to set sail. Saying goodbye to one of the most beautiful places on earth is never easy, but the adventure wasn’t over yet. We enjoyed some great sailing at first, until the wind came right...
We sail to the west side of Bora Bora and pick up a mooring in one of the most beautiful spots in the lagoon, surrounded by shallow coral heads and crystal-clear water. After dropping the hook, we jump in the dinghy and head out to the reef where we snorke...
We sail from one of the most beautiful bays we have ever spent the night in on the southeast side of Bora Bora and make our way around the island through the crystal-clear lagoon. Along the way we stop at the town dock to fill up on fresh water before grab...
We leave the Bora Bora Yacht Club and sail around the island to the far side of Bora Bora—and it turns into one of the most breathtaking sails I’ve ever experienced. Unreal turquoise water, perfect conditions, and an anchorage that honestly might be th...
Meal preparation and so much more plays a crucial role in traveling on a sailboat. While Sundays are usually dedicated to family activities. today is different. We're pushing to prepare for the next passage! Then I'll take a few moments and show you some o...
We set sail from Raiatea in French Polynesia and make the unforgettable journey to the legendary island of Bora Bora. With crystal-clear water, dramatic mountain peaks, and scenery that feels unreal, this is a place most people only dream of visiting. Afte...
Join our Patreon and join our Team SSL Crew!
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To all those contributing to our ne...
Joco's are movin on up!!! We live on a brand new HR44 ... for an afternoon :) But isn't she gorgeous!? Sure beats all the projects we have going on with Joco at the moment. Like taking apart the heat exchanger.... BOATLIFE
Thank you for all your support!!...
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