Watch Sailing & Boating Adventures Around the World tagged “Astipalea”

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

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) i...
Sailing from the Cyclades to the Dodecanese Islands, Greece (Ep 6)
Sailing Wishful Thinking

Sailing from the Cyclades to the Dodecanese Islands, Greece (Ep 6)

We sail Wishful Thinking from the Cyclades to the Dodecanese Islands, making our way to eastern Greece ready to head to Turkiye. We stop at Naxos, Koufonisia, Astipalea, Kos, Tilos and Alimia along the way. We'd planned to check out of Greece in Kos, but d...
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