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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Ep 39 Ominous Weather Vibes (Sailing Leixoes, Portugal)
Sailing Talisman

Ep 39 Ominous Weather Vibes (Sailing Leixoes, Portugal)

Leixoes, Portugal: The Doc dog is settling in nicely and we visit the city of Porto to see the Graham's port distillery. But our plans for departure are interrupted.
DIRTY DANCING AND SAILING IN THE CARIBBEAN – Chase the Story 27
Chase the Story

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...
BRAZILIAN ON BOARD! Sailing St. Martin – Chase the Story 26
Chase the Story

BRAZILIAN ON BOARD! Sailing St. Martin – Chase the Story 26

Check out our new website: (ok, it's still a work-in-progress, but it's still awesome :) And support us on Patreon: St. Martin is famous in the Caribbean for getting your boat spruced up and a place to go for much needed repairs. So we set off from Virgin Gorda in the British Virgin Isl...
THEY GOT NAKED! Sailing and Partying in the BVIs – Chase the Story 25
Chase the Story

THEY GOT NAKED! Sailing and Partying in the BVIs – Chase the Story 25

Sailing & Partying in the BVIs: THEY GOT NAKED! - Chase the Story 25 Track us across oceans in REAL TIME here: www.gtctrack.com/anonymous/turftosurf (We transmit our position from our satellite phone when we're at sea, so you can follow us at our tracker link to see where in the world Che...
WINDSURFING IN PARADISE! St. John, USVI – Chase the Story 24
Chase the Story

WINDSURFING IN PARADISE! St. John, USVI – Chase the Story 24

Windsurfing in Paradise: St. John, USVI - Chase the Story 24 Edited by Tasha Hacker & Ryan Horsnail Check out our new website! If there's one thing that's true of the crew of Cheeky Monkey, it's that we love watersports and are always willing to learn new sports! Sitting in b...
SAILING THE SPANISH VIRGIN ISLANDS!! – Chase the Story 22
Chase the Story

SAILING THE SPANISH VIRGIN ISLANDS!! – Chase the Story 22

Sailing the Spanish Virgin Islands (Puerto Rico): In this story Ryan and Tasha return from a brief trip to New York to collect two new members of crew and head out on a sailing adventure from the US Virgin Islands to the amazing Culebra Island, which is part of the Spanish Virgin Islands, which are ...
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