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 US VIRGIN ISLANDS: Sun, Sea, Snorkels & Cocktails! Ep-169
Leading the Escapade

SAILING THE US VIRGIN ISLANDS: Sun, Sea, Snorkels & Cocktails! Ep-169

Set sail to St. Croix with us in this week's adventure! After two months in St. Martin, we celebrate Janaye's 33rd birthday with beach time, Caribbean cocktails, and a sail to one of the top 10 snorkelling spots in the world! Get the sleep you deserve with up to 35% off Dream. Click and ...
We invited complete STRANGERS to join our BOAT crew! CASTAWAYS…
Sail Stillwater

We invited complete STRANGERS to join our BOAT crew! CASTAWAYS…

Call us crazy, but we recently invited some complete strangers on our upcoming bareboat charter trip! In this video we fly to Ft. Myers beach, Florida to meet up with some Castaways who will be joining our boat crew in November as we island hop throughout the British Virgin Islands on a 45' Fou...
The HARDEST Part of Cruising | See you later, Grenada!
Holly and Ray

The HARDEST Part of Cruising | See you later, Grenada!

Hurricane season is over, and we are back on the move! We officially left Grenada and made our first small hop north.⛵️The wind angle made for a bumpy trip running the engines, but crew morale was high! We dropped our anchor just before a storm arrived, causing a boat to drag anchor overnight. The s...
Boat Trip to Willy T’s! – S7:E32
Sailing Doodles

Boat Trip to Willy T’s! – S7:E32

We take a day charter sail from tortola to the World Famous Willy t's floating restaurant and bar! thanks to: This channel is funded by viewers like you. Please help us keep this channel creating great content by becoming a patron Donate Via Paypal to help
First Sailing Trip of the Year (PART 3): Sailing to an Island // Blue Moon Life Ep. 38
Blue Moon Life

First Sailing Trip of the Year (PART 3): Sailing to an Island // Blue Moon Life Ep. 38

In part 3 of this mini-series, we had another beautiful day for a sail while we traveled to our final destination!
Scuba diving Thailand Episode 181 (Sailing Catalpa)
Sailing Catalpa

Scuba diving Thailand Episode 181 (Sailing Catalpa)

This week some of us swim with a whale shark and we end up in a caves under the water. Thanks so much for joining us 🤙 To comment go to our community post on Our YouTube Page or our FaceBook Page Remember likes and shares help us out so SHARE it and SUBSCRIBE Thanks!!! Help us bring the Captain...
13 year old Captain while the family  SCUBA dives Episode 179 (Sailing Catalpa)
Sailing Catalpa

13 year old Captain while the family SCUBA dives Episode 179 (Sailing Catalpa)

This episode we dive one of the best dive sites in Thailand Richelieu Rock. We nearly don't dive and we to take turns diving leaving Catalpa adrift. Thanks so much for joining us 🤙 To comment go to our community post on Our YouTube Page or our FaceBook Page Remember likes and shares help us...
Testing Out The Sailing Lifestyle – Ep02
Breaking Waves

Testing Out The Sailing Lifestyle – Ep02

Continuing on with our sailing trip around the Gulf Islands, finding out if I could love the sailing lifestyle as much as Ben does! Keep up to date on Instagram Music: Kings of the summer - Ayokay Wildfire by John Mayer
Exploring Cayman Island: Mount Trashmore & The Crystal Caves – Untie The Lines II #55
WhiteSpotPirates

Exploring Cayman Island: Mount Trashmore & The Crystal Caves – Untie The Lines II #55

Jeff & Kim let me stay at their place in Cayman with Karl safely tied up on their dock. And I think they deserve the award for the best hosts ever because they made sure I got to see a lot from the island: the good and the bad actually. Enjoy & Ahoy, Nike & Karl Visit for more info ab...
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