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 1-6 of 6 results
SHE CRASHED IT!!! Sailing the Virgin Islands – Chase the Story 23
Chase the Story

SHE CRASHED IT!!! Sailing the Virgin Islands – Chase the Story 23

SHE CRASHED IT!!! Sailing the Virgin Islands - Chase the Story 23 We sailed Cheeky Monkey into St. John in the US Virgin Islands with a mission to run the 8 Tuff Miles road race and also to finally get our Swellpro Splash Drone off the ground and flying! The drone was a bit of a disaster but the r...
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 ...
Trailer: Sailing Around the World (Chase the Story)
Chase the Story

Trailer: Sailing Around the World (Chase the Story)

Sailing Around the World - Chase the Story Channel Trailer Turf to Surf sailing blog link: Sailing across the Atlantic was a success! We've had a blast putting together all 21 episodes taking us from La Rochelle, France to the Mediterranean and to the Caribbean. And now it's time for ...
ATLANTIC CROSSING: STUCK IN A WIND HOLE! – Chase the Story 20
Chase the Story

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...
I CAUGHT A BIG ONE!!! – Chase the Story 12
Chase the Story

I CAUGHT A BIG ONE!!! – Chase the Story 12

Things get fishy on board Cheeky Monkey as we sail across the Mediterranean from Palma de Mallorca to Gibraltar. ***SUBSCRIBE TO OUR YOUTUBE CHANNEL!!*** There were a lot of firsts on this trip, but we didn't think catching our first fish was going to be one of them! Tuna...it's what...
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, sail for two days across calm seas - sailing ...
WeBoating
Logo
Shopping cart