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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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 ...
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 days in Las Palmas, Gran Canaria, partying, d...
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 S/V Cheeky Monkey tied to th...
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 beautiful downwind sailing, a wind hole due to a...
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, sail for two days across calm seas - sailing ...
WE SHOULDN’T BE HERE – Chase the Story 10
We dropped our friends in Portocolom, Mallorca and sailed to Palma de Mallorca for a chance to discover the glitzy side of the Balearic Islands as we travel around the world. SAILING TO PALMA DE MALLORCA, SPAIN Story by Tasha Hacker (featuring Ryan Horsnail) Music from Soundcloud: I Got U Baby -...
CHAMPAGNE BOTTLE VS. SABRE: A BOAT IS BORN – Chase the Story 8
Our friend Kari flew to Menorca to spend her birthday sailing, so we put the boat repairs aside to have some fun and name the boat. It was a christening that turned quite elaborate when friends turned up with a champagne sabre to gallantly sheer the top off a bottle! SUBSCRIBE TO OUR YOUTUBE CHANNEL...