Watch Sailing & Boating Adventures Around the World tagged “Travel vlogs” – Page 4 of 4

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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2. How NOT to buy a sailboat in Greece!! | Buying a Sailboat in Europe |
Sailing Sunday

2. How NOT to buy a sailboat in Greece!! | Buying a Sailboat in Europe |

Heading to Greece from Australia to survey a sailboat in hopes to purchase, only to find out its falling apart!!!!
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 pa...
ATLANTIC CROSSING – ARE WE READY? – Chase the Story 18
Chase the Story

ATLANTIC CROSSING – ARE WE READY? – Chase the Story 18

The crew prepare for their first ocean crossing on Cheeky Monkey - approximately 20 days of open sea sailing across the Atlantic. ***ENJOY THE VIDEO? SUBSCRIBE TO OUR CHANNEL!*** Preparing to sail across the Atlantic - Sailing Cheeky Monkey After five d...
CANARY ISLANDS: HORSING AROUND – Chase the Story 17
Chase the Story

CANARY ISLANDS: HORSING AROUND – Chase the Story 17

Once we'd recovered from celebrating Kristi's birthday, we set out on an adventure across the barren hills of Gran Canaria, Spain. ***SUBSCRIBE TO OUR YOUTUBE CHANNEL!!!*** Sailing over from Morocco, we'd arrived in Gran Canaria a few days before. Leaving...
The Atlantic Crossing Promo (Sailing – Chase the Story)
Chase the Story

The Atlantic Crossing Promo (Sailing – Chase the Story)

Sailing Adventure: The crew of Cheeky Monkey - now three Americans, two French and a Brit - head out across the Atlantic for one hell of a ride. Leaving Morocco and heading to the Caribbean, with just one stop in the Canary Islands, the crew encounter beau...
WAKEBOARDING IN PARADISE – Chase the Story 11
Chase the Story

WAKEBOARDING IN PARADISE – Chase the Story 11

Sailing across the Mediterranean: wakeboarding. The Cheeky Monkey crew leave Palma, Mallorca, and set off east across the Mediterranean in search of the perfect beach for wakeboarding. New crew members Kristi and Meg, along with friends John and Chris, s...
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