Watch Sailing & Boating Adventures Around the World tagged “Caribbean” – Page 2 of 156
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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It’s our last day in Greece aboard the charter catamaran, sailing from the beautiful island of Agistri back to Athens. As we entered the marina, a line of a couple dozen boats all tried to dock at once with the wind picking up—things got a little hecti...
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On our next-to-last day sailing in Greece with Sailing Miss Lone Star, we had some of the best moments of the trip! 🌊⛵
We pushed the boat hard in brisk winds on the way to the beautiful Greek town of Poros, flying across the water under sail. The fol...
Join us for a short but beautiful downwind sail from Aegina to Agistri, where things get interesting as I attempt a creative (and slightly unusual) mooring. After some relaxing beach time, we head to the Jamaica Yacht Club for an unforgettable Greek BBQ an...
We continue our Greek island adventure with Sailing Miss Lone Star as we sail from Vathy to Aegina. Along the way we stumble across something unusual on the cliffsides… but the day finishes in true Mediterranean style — with a dip in crystal-clear wate...
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We're island hopping, I finally get some time to enjoy my MS Bikinis! We've had it rough lately but this was the ah-ha moment!! Come enjoy it with us!
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We’re back sailing in Greece with Miss Lone Star aboard a Lagoon 38 catamaran! 🌊⛵️
With the wind blowing over 20 knots, we reefed down twice and still flew along at 8 knots on our way from Aegina to one of my favorite harbors in the Saronic Island...
We’re in Greece! 🇬🇷
In this episode, I fly into Athens to meet up with fellow YouTuber Sailing Miss Lone Star! @SailingMissLoneStar our very first collaboration. We chartered a beautiful catamaran and set sail on our maiden voyage together. Joinin...
After weeks of hard work keeping my boat in shape, I finally wrap up the last round of repairs and set sail for Maryland. Along the way, I enjoy the last miles of the trip before hauling the boat out of the water, where it will be stored safely for the sum...
I set out from Charleston, South Carolina, on a solo sailing journey of nearly 500 miles—rounding the notorious Cape Hatteras and heading up into the Chesapeake Bay. Along the way, I face changing weather, long nights at the helm, and the beauty (and cha...
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In this one we'll navigate the challenges of boat maintenance and the stresses of living remotely. Then we'll hike to the Blue Hole and jump right in!
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After sailing more than 400 miles from the Bahamas to Charleston, SC, it’s time to tackle all the boat work I’ve been putting off. In the Bahamas, it’s nearly impossible to get the parts and materials you need—but now that I’m stateside, it’s f...
We sail more than 400 nautical miles across open ocean, leaving the Bahamas behind and heading back to the U.S. coast — destination: Charleston, South Carolina. The weather throws us some surprises, the seas don’t make it easy, and morale is tested. Bu...
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Experience a day filled with exciting water activities like snorkeling and exploring shark alley. We deal with ongoing issues with our water maker, showcasing frustrations and last ditch efforts to find solutions.
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Beautiful Jennifer rejoins the crew just in time for one last unforgettable beach day in the Bahamas! We sail up to stunning Spanish Cay, soaking in the final days of sunshine, clear blue water, and tropical vibes before setting our course back to the USA....
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Sailing solo through the stunning Abacos, I make my way from Great Guana Cay up to Green Turtle Cay in the Bahamas. But along the way, I spot something totally unexpected — a yacht, wrecked and abandoned on the beach with no one in sight.
Curiosity gets...
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We complete our loop; Antigua, Sint Maarten, British Virgin Islands, USVI, St Croix, and Guadeloupe.
This trip is always bittersweet, given that it marks our return home to Antigua. We love Antigua, and it’s our home base, but it means the adventure sa...
In this episode, we’re dealing with one of the most frustrating parts of liveaboard life—ongoing boat repairs that never seem to end. Our watermaker decides to act up right when we need it most, and no matter how many parts we replace or seals we glue,...
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