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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ep44 – Sailing Long Island – Greenport, Huntington & New York – HR54 Cloudy Bay – Sep 2018
Sail Cloudy Bay

ep44 – Sailing Long Island – Greenport, Huntington & New York – HR54 Cloudy Bay – Sep 2018

After a night in Orient Bay near Greenport NY, s/v Cloudy Bay (Hallberg-Rassy 54) leaves the quiet anchorage at sunrise with a long day sail to Huntington NY. So this sailing trip takes us along the north shore of Long Island, from the north fork to Huntington. Once in Huntington we take a mooring b...
ep42 – Sailing Long Island – Sag Harbor & The Hamptons – Hallberg-Rassy 54 Cloudy Bay – Sep 2018
Sail Cloudy Bay

ep42 – Sailing Long Island – Sag Harbor & The Hamptons – Hallberg-Rassy 54 Cloudy Bay – Sep 2018

s/v Cloudy Bay (Hallberg-Rassy 54) leaves Fisher Island CT on a foggy morning and has a slow and calm sailing trip to the south fork of Long Island NY. Not the most thrilling sailing adventure, but it was nevertheless a very pleasant sail. We anchor in Sag Harbor, where we wait for the sky to clear....
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