Watch Sailing & Boating Adventures Around the World

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SHE’S A THRILL TO SAIL! – Ep 226
Sailing Jibsea

SHE’S A THRILL TO SAIL! – Ep 226

We embark on a sail from the half French, half Dutch island of of Saint Martin/Sint Maarten to Antigua, covering 100 nautical miles across the Caribbean. We face a winch malfunction shortly after picking up anchor. See how we solve this issue on the go. We sail past a couple other Caribbean islands,...
Booby trapped TREASURE ISLAND! [Ep21 RED SEAS]
Sailing Red Seas

Booby trapped TREASURE ISLAND! [Ep21 RED SEAS]

It's time to go sailing - to a deserted island! We've been working hard on Indi and we need a break, so it's off to the island of Tintamarre to spend some time exploring off grid. Not much goes to plan, but thats par for the course with us! Come and hang out in paradise! 🙌🏻 Support u...
ep63 – Sailing Anguilla – Best Beaches Anguilla – Hallberg-Rassy 54 Cloudy Bay – Feb-Mar 2019
Sail Cloudy Bay

ep63 – Sailing Anguilla – Best Beaches Anguilla – Hallberg-Rassy 54 Cloudy Bay – Feb-Mar 2019

Sailing St.Martin to Anguila and visit its stunning beaches and resorts. Some of the best beaches in the world we would say. Anguilla is probably the best sun & sand destination in the Caribbean. Following our short trip to the island of Saba, s/v Cloudy Bay (Hallberg Rassy 54) continues the cr...
Ep 39. Sailing Anguilla to BVI & Valentines on a Desert Island
The Daley Adventure

Ep 39. Sailing Anguilla to BVI & Valentines on a Desert Island

Ep 39. Those of you guys who have been following for a while will know about our issues with our Gennaker. More precisely, that bloody sail has been a nightmare for us that culminated in the middle of the Atlantic when it split into 2 halves. The sail loft in Saint Martin were great and pointed o...
Ep 38. Sailing around the World means: Fixing things in beautiful places.  (Sailing Susan Ann II)
The Daley Adventure

Ep 38. Sailing around the World means: Fixing things in beautiful places. (Sailing Susan Ann II)

Ep 38 WE HEAR THE BABY’S HEART BEAT! At long last we’ve reached the 12 week point in Hayley’s pregnancy and head to a great Doc in St Martin and see and hear our little angel. You’ll have to watch thru to the end to see how it goes. We start this episode in Anguilla doing all the regular maintena...
Ep. 10 – The Road to The Bucketlust (Culebra, St. Thomas, St. Martin)
S/V Full Send

Ep. 10 – The Road to The Bucketlust (Culebra, St. Thomas, St. Martin)

We start heading back East towards St. Martin for The BucketLust's New Year's Eve route. We pick up a few friends in St. Thomas to make the passage with us, and have another run in with the Coast Guard. This time it's with the Dutch. Enjoy!!! Huge THANKS to our Patrons for your conti...
Ep 37.  Super Bowl Sunday, Ship Wrecks and Saint Martin.  (Sailing Susan Ann II)
The Daley Adventure

Ep 37. Super Bowl Sunday, Ship Wrecks and Saint Martin. (Sailing Susan Ann II)

Thanks for watching and continuing on our adventure with us. We know it isn’t easy with such irregular uploads but your support is very much appreciated. This episode starts on Saint Martin and we end up on Anguilla, so really we visited The Netherlands, France and the UK all in a couple of days. ...
Ep. 7 – Anguilla to BVI
S/V Full Send

Ep. 7 – Anguilla to BVI

We head off on our 80+ nautical mile crossing from Road Bay, Anguilla to the Spanish Town, Virgin Gorda, British Virgin Islands. We had almost no wind on the way over, but the 10 minutes of dolphins accompanying us more than made up for not being able to sail. Huge THANKS to our Patrons for your co...
Ep. 6 – Nevis, St. Maarten, Anguilla
S/V Full Send

Ep. 6 – Nevis, St. Maarten, Anguilla

In this episode, we head from Guadalupe to Nevis, Sint Maarten/St. Martin, and Anguilla. We get a few jobs fixed in Sint Maarten, get blown back by a passenger jet, and flip our dinghy rendering our outboard motor inoperable...... We have two more guest come aboard for the ride as well. Huge THANKS...
SSL 9 ~ THE PARTY IS OVER!
Captain Rick Moore

SSL 9 ~ THE PARTY IS OVER!

Thanks so much to all our new supporters on Patreon! If you'd like to support our SSL Videos on Patreon, find us here! To view our new extended version SSL episodes AD-FREE with previously deleted scenes, full length interviews, dive scenes, drone aerials and more, visit our new Vimeo On Dema...
SSL 7 ~ Road Bay Sunset Tour ~ Anguilla Island, CARIBBEAN!
Captain Rick Moore

SSL 7 ~ Road Bay Sunset Tour ~ Anguilla Island, CARIBBEAN!

Thanks so much to all our new supporters on Patreon! If you'd like to support our SSL Videos on Patreon, find us here! To view our new extended version SSL episodes AD-FREE with previously deleted scenes, full length interviews, dive scenes, drone aerials and more, visit our new Vimeo On Dema...
SSL 6 ~ We LOVE You Sandy Island! ~ Part 2 of Anguilla, CARIBBEAN
Captain Rick Moore

SSL 6 ~ We LOVE You Sandy Island! ~ Part 2 of Anguilla, CARIBBEAN

Thanks so much to all our new supporters on Patreon! If you'd like to support our SSL Videos on Patreon, find us here! To view our new extended version SSL episodes AD-FREE with previously deleted scenes, full length interviews, dive scenes, drone aerials and more, visit our new Vimeo On Dema...
SSL 5 ~ Bye Bye Jessie, HELLO ANGUILLA!
Captain Rick Moore

SSL 5 ~ Bye Bye Jessie, HELLO ANGUILLA!

Thanks so much to all our new supporters on Patreon! If you'd like to support our SSL Videos on Patreon, find us here! To view our new extended version SSL episodes AD-FREE with previously deleted scenes, full length interviews, dive scenes, drone aerials and more, visit our new Vimeo On Dema...
DIRTY DANCING AND SAILING IN THE CARIBBEAN – Chase the Story 27
Chase the Story

DIRTY DANCING AND SAILING IN THE CARIBBEAN – Chase the Story 27

DIRTY DANCING AND SAILING IN THE CARIBBEAN -- Chase the Story 27 Edited by Bruna Toledo de Arcangelo -- she is a professional videographer and you can find all her other amazing works here: / Instagram: @brunaatoledo We took a little break from all the boat work on Cheeky Monkey to sail to Anguil...
Crazy Anguilla Sailboat Race
Distant Shores TV

Crazy Anguilla Sailboat Race

We tangled our mast in their rigging. We nearly sank! We had an amazing day! Anguilla Boat Racing is VERY exciting and I was very lucky to get to be aboard one of the island sloops for the first major race of the season. The boats are packed with 21 crew, 2 of whom spent most of the race bailing...
Chasing the Story in Anguilla (EP 15 – Monday Never Sailing)
Monday Never

Chasing the Story in Anguilla (EP 15 – Monday Never Sailing)

This is what happens when you get too many people who live on boats together and put them on an island during the biggest fish festival of the year. In this episode, we get to hang out with some of our favorite cruiser friends Ryan and Tasha and their amazing crew Kristi and Bruna. We sail to Anguil...
Most Dangerous Airport in the World! (Sailing La Vagabonde) – Ep. 10
Sailing La Vagabonde

Most Dangerous Airport in the World! (Sailing La Vagabonde) – Ep. 10

Checked out one of the most dangerous airports in the world in Saint Maarten. Got sand blasted on the beach and it hurt. Explored an abandoned hotel. We love the Caribbean and seafood! Sailing a bit of St Martin, Anguilla & St Barts. Slowly making our way down towards Grenada for the hurricane s...
St Maarten, SXM – LIVING IN THE ISLANDS – Trip To Anguilla, CARIBBEAN!
Captain Rick Moore

St Maarten, SXM – LIVING IN THE ISLANDS – Trip To Anguilla, CARIBBEAN!

Video filmed in St Maarten, SXM, and Anguilla in the CARIBBEAN. Song "LIVING IN THE ISLANDS" by our friend Brian Neale but he sure sounds like Jimmy Buffett doesn't he? And actually, Brian has played on stage with Jimmy Buffett before! A very entertaining song, Brian has his own un...
Mes Amis Villa, St Martin, SXM
Captain Rick Moore

Mes Amis Villa, St Martin, SXM

First cut of a new villa video for the most extravagent villa on all of St Martin, Mes Amis. 7 acres of beautifully landscaped property with an 11-bedroom villa situated on top of a cliff overlooking the Caribbean Sea with Anguilla in the distance.
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