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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Did Our Charter Gambit Work? | Mid Season Update
BoatFools Sailing

Did Our Charter Gambit Work? | Mid Season Update

@boatfools #sailboatcharter #bareboatcharter #morgan382 #morgan384 #sailingmaine Did Our Charter Gambit Work? | Mid Season Update Was putting our own sailboats into charter a brilliant idea—or a terrible mistake? We're halfway through our first charter season, and it's time for an hone...
  • Aug 22, 2026
  • Language: EN
  • Play Time: 00:09:18
Fish ON! Sailing the deep waters of St. Croix. Day #2
Sail Stillwater

Fish ON! Sailing the deep waters of St. Croix. Day #2

Sailing Charter Day 2 | St. John to St. Croix | Rough Seas, Fishing & Christiansted Harbor and Boardwalk. Day 2 of our Virgin Islands sailing charter takes us offshore as we leave St. John, USVI and sail across deep open water to St. Croix. With rough seas and steady wind, this passage was a t...
  • Dec 26, 2025
  • Language: EN
  • Play Time: 00:11:21
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