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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Sailing Florida Keys Back-Country

Matt’s brother Andrew, visited Sailing Bye Felicia for his birthday. Matt and Lisa take home to downtown Key West to grab some supplies. They stock up on fishing gear and speargun equipment. And who can’t resist a pie from Kermit’s. Then they set sail to Boca Grand. This is their longest sail yet! T...

Sep 17, 2022
Language: EN
Play Time: 00:05:13

Dragging anchor and smashing into a pier in the Dry Tortugas

Back to the keys for more fun. We find and uninhabited islands for ourselves, drag anchor, and encounter my first 50kt squall! [email protected] If you’re interested in contributing, links for patreon, venmo or paypal are below: Follow me on instagram @SamHolmesSailing

Jul 06, 2020
Language: EN
Play Time: 00:17:13

For Whom the Ship’s Bell Tolls

So of course a visit to Key West must include a visit to the home of Ernest Hemingway. I also have to check out the famous (or infamous) nightlife on Duval street and I am pleased to find a vibrant live music scene. I purchase a second hand Phantom 3 drone but find out that I cannot fly it in Key...

Apr 03, 2019
Language: EN
Play Time: 00:16:55

Watch Sailing & Boating Adventures Around the World

Sailing Florida Keys Back-Country

Dragging anchor and smashing into a pier in the Dry Tortugas

For Whom the Ship’s Bell Tolls

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