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.

Showing 1-9 of 9 results
SAILING THE SPANISH VIRGIN ISLANDS!! – Chase the Story 22
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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: WE MADE IT!! – Chase the Story 21
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Atlantic Crossing: WE MADE IT!! – Chase the Story 21

We made it! Sailing across the Atlantic Ocean after 20 days at sea, sailing vessel Cheeky Monkey finally arrives to the Caribbean to the beautiful island of Antigua. It was a test of time for our six crew on board - did we make it with empty diesel tanks? Did we make it before Christmas? Did we make...
ATLANTIC CROSSING: STUCK IN A WIND HOLE! – Chase the Story 20
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ATLANTIC CROSSING: STUCK IN A WIND HOLE! – Chase the Story 20

Atlantic Crossing: Stuck in a Wind Hole! (Story 20) Sailing across the Atlantic Ocean comes with the challenge of tracking the weather and plotting a course that will take us across to the Caribbean with maximum wind and minimum motoring. When a storm on the north Atlantic sucks all the wind out o...
SAILING THE ATLANTIC: SHE WENT OVERBOARD!! – Chase the Story 19
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SAILING THE ATLANTIC: SHE WENT OVERBOARD!! – Chase the Story 19

Sailing the Atlantic with Cheeky Monkey is finally here! Our first sailing video of Cheeky Monkey racing against the clock across the Atlantic Ocean to the Caribbean. ***WANT MORE?? SUBSCRIBE TO OUR CHANNEL!*** The time for preparing is over! We slip lines from the Canary Islands to adventure i...
ATLANTIC CROSSING – ARE WE READY? – Chase the Story 18
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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
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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...
WE COULDN’T FIND THE TURKEY – Chase the Story 16
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WE COULDN’T FIND THE TURKEY – Chase the Story 16

We set out in across the Atlantic and our first meal at sea is prepared by the Americans on board. ***SUBSCRIBE TO OUR YOUTUBE CHANNEL FOR UPDATES!!!*** Turf to Surf Blog Link: On November 26, 2015, the six crew of sailing vessel Cheeky Monkey set out with two missions - 1) show our French crew m...
20,000 MILE JOURNEY BEGINS – Chase the Story 9
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20,000 MILE JOURNEY BEGINS – Chase the Story 9

After months of prepping Cheeky Monkey to start her journey sailing around the world, she is finally ready! We are off sailing to Mallorca, and the voyage beings with some impromptu guests on board. Film by Tasha Hacker Links: Turf to Surf Blog: Chase the Story Instagram: Chase the Story Google+...
CHAMPAGNE BOTTLE VS. SABRE: A BOAT IS BORN – Chase the Story 8
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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...
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