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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New England sailing adventure! Hoist the Maine!
Sail Stillwater

New England sailing adventure! Hoist the Maine!

Join us aboard SV Kleos as we sail the Maine coast from Kittery, Maine to Old Orchard Beach and back on an unforgettable New England sailing adventure. If you watched Brian’s previous Bermuda to New Hampshire sailing trip, you may recognize SV Kleos — this is the same Amel Super Maramu sailboat he ...
  • Aug 16, 2026
  • Language: EN
  • Play Time: 00:19:25
ep35 – Sailing Portsmouth NH to Gloucester & Cape Cod MA – Hallberg-Rassy 54 Cloudy Bay – Aug 2018
Sail Cloudy Bay

ep35 – Sailing Portsmouth NH to Gloucester & Cape Cod MA – Hallberg-Rassy 54 Cloudy Bay – Aug 2018

s/v Cloudy Bay (Hallberg-Rassy 54) continues the sailing adventure southwards. In this video we are sailing Cloudy Bay from Portland ME to Portsmouth NH, where we have an overnight. We visit Portsmouth briefly in the evening - it is a very beautiful town and we wished we had time to see more of it. ...
  • Sep 06, 2018
  • Language: EN
  • Play Time: 00:23:56
ep34 – Sailing Maine – Camden, Boothbay Harbor, Portland – Hallberg-Rassy 54 Cloudy Bay – Jul 2018
Sail Cloudy Bay

ep34 – Sailing Maine – Camden, Boothbay Harbor, Portland – Hallberg-Rassy 54 Cloudy Bay – Jul 2018

From Camden, s/v Cloudy Bay (Hallberg-Rassy 54) motored in thick fog to Boothbay Harbor, where the boat was moored for 3 weeks while we took a trip to Europe. We returned from our vacation to lots of deliveries and had a few days of boat maintenance, before sailing to Portland, our last port in Main...
  • Sep 04, 2018
  • Language: EN
  • Play Time: 00:15:01
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