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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Shaking It Out – Sailing in the Keys
Gone with the Wynns

Shaking It Out – Sailing in the Keys

After our last day of skinny water sailing, an unexpected squall and a bad anchorage today is pretty darn awesome! Join the Crew on Patreon: Read the full story and get the extra deets: We "woke" up from our zero sleep night and for some crazy reason we decided not to start the engine...
Hurricane Delays & Greeted By Dolphins – Now We’re Sailing!
Gone with the Wynns

Hurricane Delays & Greeted By Dolphins – Now We’re Sailing!

Hurricanes obviously don't follow our website and don't care we're embarking on our shakedown cruise. Read the full story and get the extra deets: Join the Crew on Patreon: About a week ago we attempted to sail to the keys but the hurricanes started brewing in the Atlantic and we ...
Learn How To Sail || Our First Solo Sail Part 2 (s/v Curiosity)
Gone with the Wynns

Learn How To Sail || Our First Solo Sail Part 2 (s/v Curiosity)

Everything doesn't go as planned and we end up on a nail biting adventure! Join the Crew and get more involved on Patreon: See the post that goes with this video: Today our plan is to sail from Lake Worth Inlet (West Palm Beach, FL) to the St. Lucie Inlet (Stuart, FL). Our planned depar...
Learn How To Sail || Our First Solo Sail Part 1 (s/v Curiosity)
Gone with the Wynns

Learn How To Sail || Our First Solo Sail Part 1 (s/v Curiosity)

It's our first solo sail and we pretty much nailed it...or maybe not, but I'd still call it a success. We're going coastal baby! Join the Crew and get more involved on Patreon: Subscribe to get the latest Videos: See the post that goes with this video: We've finally done it...
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