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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We are battling the ferries of the Aegean around Despotiko! (Sailing Dakini – Leave to Roam Ep. 82)

After a couple of nights with friends in Sifnos in the Cyclades we sail east to an amazing anchorage between Despotiko and Antiparos. This move is prompted by the weather but we are stunned by our strongest winds ever while underway at 38kts. We end up dumping the main completely but we do make it s...

Feb 20, 2026
Language: EN
Play Time: 00:20:53

Sailing across the Cyclades in March – Cold, stormy & AMAZING! Winter / off season in Greece (Ep 14)

We finally launch Wishful Thinking in Leros, Greece, ready for our second sailing season. We're nervous about our launch as we've done lots of work below the waterline and found a leak after launching last year. Our friends (along with their cat, Chicho) invite us over for a boat tour of t...

Jul 19, 2024
Language: EN
Play Time: 00:16:22

Watch Sailing & Boating Adventures Around the World

We are battling the ferries of the Aegean around Despotiko! (Sailing Dakini – Leave to Roam Ep. 82)

Sailing across the Cyclades in March – Cold, stormy & AMAZING! Winter / off season in Greece (Ep 14)

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