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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The Pros and Cons of Sailing in Anguilla

Anguilla should be on all sailor's lists to visit, if only for a short stay. Pristine beaches and beautiful coastlines make it worthwhile. Learn how to sail Anguilla while keeping the costs down in this video. Why did we go to Anguilla ? Anguilla is not a popular destination for sailors, b...

Jun 06, 2026
Language: EN
Play Time: 00:11:28

DIRTY DANCING AND SAILING IN THE CARIBBEAN – Chase the Story 27

DIRTY DANCING AND SAILING IN THE CARIBBEAN -- Chase the Story 27 Edited by Bruna Toledo de Arcangelo -- she is a professional videographer and you can find all her other amazing works here: / Instagram: @brunaatoledo We took a little break from all the boat work on Cheeky Monkey to sail to Anguil...

Jun 16, 2016
Language: EN
Play Time: 00:15:17

Watch Sailing & Boating Adventures Around the World

The Pros and Cons of Sailing in Anguilla

DIRTY DANCING AND SAILING IN THE CARIBBEAN – Chase the Story 27

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