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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Rained Out in San Blas
Sailing Big Lost

Rained Out in San Blas

We’re a family sailing full-time, exploring the Caribbean and Central America aboard our sailing catamaran Big Lost. New episodes every Tuesday at 10:30 AM ET. We’ve had rain off and on since arriving in Panama, and as we begin exploring the San Blas—now learning their true name, the Guna Yala Isla...
  • Dec 02, 2025
  • Language: EN
  • Play Time: 00:20:53
Journey to the most protected bay in Costa Rica | Sailing Sitka Ep 153
Sailing Sitka

Journey to the most protected bay in Costa Rica | Sailing Sitka Ep 153

In this episode of Sailing Sitka, Jay and Kenna sail the squally and sloppy seas from Quepos to Golfito, down the pacific costa of Costa Rica. After having numerous encounters with rolley anchorages, we finally make landfall in a bay that is often mistaken for a lake, thats how protected it is. Some...
  • Feb 02, 2025
  • Language: EN
  • Play Time: 00:25:15
Work hard, PLAY HARDER – Boys surf trip to El Salvador – Episode 40
Sailing Parlay Revival

Work hard, PLAY HARDER – Boys surf trip to El Salvador – Episode 40

After working full time for 5 weeks straight on our hurricane damaged catamaran, grinding fibreglass in the Guatemalan heat, we take a well deserved boys trip to El Tunco, in El Salvador, where we make a bunch of new friends and surf local spots Bocana, Bocanita, Sunzal and Punta Roca. We then get b...
  • Nov 06, 2019
  • Language: EN
  • Play Time: 00:16:27
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