Watch Sailing & Boating Adventures Around the World – Page 2 of 2

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 25-38 of 38 results
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...
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...
The Atlantic Crossing Promo (Sailing – Chase the Story)
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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
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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
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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 -...
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...
RESCUED AT SEA – Chase the Story 7
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RESCUED AT SEA – Chase the Story 7

THE ONE WHERE I GET RESCUED BY HELICOPTER ROWING ACROSS THE MEDITERRANEAN. Subscribe to our YouTube Channel to follow our story!!! Sailing 1400 miles from La Rochelle, France to Ibiza, Spain clearly wasn't enough of a challenge for Tasha, so she signed up this challenge: rowing 300 miles acro...
WE NEED TO GET TO BARCELONA – Chase the Story 6
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WE NEED TO GET TO BARCELONA – Chase the Story 6

Ryan & Tasha go sailing from Ibiza to Barcelona on a mission to get to Port Vell before the start of the Shoreseeker Challenge. SUBSCRIBE TO OUR YOUTUBE CHANNEL FOR UPDATES!!! Marina in Barcelona: OneOcean Port Vell ( Rowing Race from Barcelona to Sardinia: Shoreseeker Challenge ( Story by Ta...
WE WON’T GIVE UP, SAILING ONWARDS TO IBIZA! – Chase the Story 4
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WE WON’T GIVE UP, SAILING ONWARDS TO IBIZA! – Chase the Story 4

Having had to stop in Southern Spain due to terrible weather, we head out again on our journey across the Mediterranean to Ibiza. SUBSCRIBE TO FOLLOW THE STORY! Cheeky Monkey completes the 1400-nautical-mile shakedown cruise, sailing from La Rochelle, France to Ibiza, Spain. Film by Tasha Hacker ...
SAILING FROM FRANCE TO SPAIN: SHAKEDOWN CRUISE – Chase the Story 3
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SAILING FROM FRANCE TO SPAIN: SHAKEDOWN CRUISE – Chase the Story 3

With the new boat ready to leave the dock, we attempt a 1,400 mile passage to test the systems and in search of warmer weather. SUBSCRIBE TO NEW EPISODES!!! After a month of hanging out in La Rochelle, France, doing post-factory work on our new Fountaine-Pajot Helia 44, it is time to put her to th...
THE MAKING OF A SAILBOAT – Chase the Story 1
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THE MAKING OF A SAILBOAT – Chase the Story 1

We're super excited as we head to France to see the first stages of our new sail boat that is going to take us on our world voyage! Don't forget to subscribe to our new channel!! Sailing Around the World. Cheeky Monkey is the name of the sailboat. Tasha & Ryan are the captains. The a...
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