Watch Sailing & Boating Adventures Around the World tagged “Caribbean”

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Dutch vs French St. Martin: Cheap Lagoon Living… Then We LEFT
Sailing Doodles

Dutch vs French St. Martin: Cheap Lagoon Living… Then We LEFT

We explore Sint Maarten starting on the Dutch side — from planes screaming overhead at Maho Beach to cruising the surprisingly affordable liveaboard scene on Simpson Bay Lagoon. Living aboard here can be way cheaper than you might expect, and the vibe i...
Who Won My Boat?
Sailing Doodles

Who Won My Boat?

The boat drawing is complete — and we have a winner. The drawing was done automatically, but the reserve was not met. As promised, that meant the winner would receive the partial cash equivalent of the funds raised rather than the boat itself. Right af...
⛵️PROVISIONING for 6 MONTHS SAILING the CARIBBEAN! How Much$$| Hallberg Rassy 352
Sailing Joco

⛵️PROVISIONING for 6 MONTHS SAILING the CARIBBEAN! How Much$$| Hallberg Rassy 352

WE ARE LEAVING ST MARTIN!!!!! But first - Provisioning Time. Come along and see a full day of shopping for random sh*t you never wanted to spend money on in the first place & we'll tell you how much it costs! Thank you for all your support!!! Busines...
Tiny Bikinis, Big Vibes | Wild Night in St. Barts
Sailing Doodles

Tiny Bikinis, Big Vibes | Wild Night in St. Barts

We kick things off soaking up the sun at Nikki Beach, easing into another unreal day in Saint Barthélemy. From there it’s poolside vibes, cold drinks, and Yosaira absolutely stealing the show in a tiny bikini that turns heads everywhere we go. That nig...
Anchored on an Uncharted Wreck… Then He Took Me Tubing While Mad 😳 – The Lazy Geckos Ep. 344
Lazy Gecko Sailing & Adventures

Anchored on an Uncharted Wreck… Then He Took Me Tubing While Mad 😳 – The Lazy Geckos Ep. 344

Join us as a fun day unfolds in the Bahamas with activities like snorkeling, tubing, and exploring a sunken wreck. The day highlights the joy of family bonding and adventure, concluding with reflections on creating lasting memories and preparing for their ...
SSL750 ~ Return to CHAOS…
Captain Rick Moore

SSL750 ~ Return to CHAOS…

Join our Patreon and join our Team SSL Crew! http://www.patreon.com/SailingSophisticatedLady Come and join us realtime at: http://www.facebook.com/groups/SSLBackstage http://www.instagram.com/SailingSophisticatedLady To all those contributing to our ne...
⛵️LEAVING THE BOATYARD BEHIND | New SAILING ADVENTURES begin NOW! (starting with seasick🤢)
Sailing Joco

⛵️LEAVING THE BOATYARD BEHIND | New SAILING ADVENTURES begin NOW! (starting with seasick🤢)

We break FREE from the boatyard AND the lagoon to anchor out in crystal clear waters...FINALLY!!! It's been 13.5 months ON THE HARD and we don't quite have our sea legs yet and we get TOSSED around like rag dolls. But there is still work to be done so we ...
From French Chic to St. Barts Heat 🔥 | Caribbean Sailing Gets Wild
Sailing Doodles

From French Chic to St. Barts Heat 🔥 | Caribbean Sailing Gets Wild

We start the day soaking up French Caribbean vibes at Grand Case, spending the afternoon at the iconic Rainbow Café. From there, we set sail for a short hop over to Anse Marcel, grabbing a marina slip and enjoying a relaxed night onboard. The next mornin...
New Crew, New Catamaran & a Wild Night in St. Martin
Sailing Doodles

New Crew, New Catamaran & a Wild Night in St. Martin

We fly to the French side of St. Martin and kick off a brand-new sailing adventure aboard a 50-foot Leopard catamaran with an all-new crew. After provisioning and getting settled, we set sail along the coast toward the iconic anchorage at Grand Case. Once...
⛵️after 9490 HOURS IN THE BOATYARD… | SPLASH DAY! | Hallberg Rassy 352
Sailing Joco

⛵️after 9490 HOURS IN THE BOATYARD… | SPLASH DAY! | Hallberg Rassy 352

It has been a LOOOOOONG 9490 HOURS IN THE BOATYARD & we are FINALLY ready to SPLASH! In this episode we do the final push to launch !!!!!!!!!!!! Thank you for all your support!!! Business/Collab Inquiries [email protected] If you’re enjoying our ...
The Sailing Dream: This is what “SOMEDAY” looks like!  – The Lazy Geckos Ep. 343
Lazy Gecko Sailing & Adventures

The Sailing Dream: This is what “SOMEDAY” looks like! – The Lazy Geckos Ep. 343

The journey starts from Nassau Harbor, where the crew prepares the boat and discusses their route. Then we're sailing away! After a stop at Chub Marina for diesel, the crew will share boating experiences. Approaching a remote anchorage, they discover an un...
We’re Leaving French Polynesia… What’s Next?
Sailing Doodles

We’re Leaving French Polynesia… What’s Next?

Our final day in French Polynesia was one to remember. 🌴 We set out on a long hike through the jungle to some incredible waterfalls, soaking up every last bit of this amazing place before it was time to go. That evening we shared one final night onboar...
A Perfect Lazy Sail in Paradise | Tahaa to Raiatea
Sailing Doodles

A Perfect Lazy Sail in Paradise | Tahaa to Raiatea

We set sail on one of those rare, perfect days in French Polynesia—a slow, easy cruise from Tahaa to Raiatea. No rush, no schedule… just smooth water, warm sun, and island vibes. We enjoyed lunch underway while Chloe relaxed on deck, soaking it all in...
Cruising Life: Is it REALLY that much work? See our daily routine! – The Lazy Geckos Ep. 342
Lazy Gecko Sailing & Adventures

Cruising Life: Is it REALLY that much work? See our daily routine! – The Lazy Geckos Ep. 342

Let's explore the daily life on a boat, focusing on meal preparation, laundry management, and the challenges of cruising. We'll share family moments and the joy of discovering new places, along with routine tasks like shopping for supplies and ensuring the...
Bikini Dancing, Rum & Sharks | Sailing French Polynesia
Sailing Doodles

Bikini Dancing, Rum & Sharks | Sailing French Polynesia

Island hopping around Taha’a in French Polynesia turned into one of our wildest days yet. Chloe was dancing on deck in her bikini as we sailed through crystal-clear lagoons, stopped to tour a local rum distillery, and then headed out to the barrier reef ...
Sailing the British Virgin Islands | The Ultimate 7-Day Yacht Charter Movie (Full Trip)
Sailing Doodles

Sailing the British Virgin Islands | The Ultimate 7-Day Yacht Charter Movie (Full Trip)

Ever wondered what it’s really like to charter a yacht in the British Virgin Islands? This is the complete experience. In this full-length sailing movie, I combined all 7 episodes from our BVI charter into one 1.5-hour, start-to-finish journey showing e...
Leaving Bora Bora Was Hard… But This Made It Worth It
Sailing Doodles

Leaving Bora Bora Was Hard… But This Made It Worth It

After four unforgettable nights in Bora Bora, it was finally time to set sail. Saying goodbye to one of the most beautiful places on earth is never easy, but the adventure wasn’t over yet. We enjoyed some great sailing at first, until the wind came right...
Sailing Bora Bora: Sharks, Coral Reefs & a Perfect Downwind Run
Sailing Doodles

Sailing Bora Bora: Sharks, Coral Reefs & a Perfect Downwind Run

We sail to the west side of Bora Bora and pick up a mooring in one of the most beautiful spots in the lagoon, surrounded by shallow coral heads and crystal-clear water. After dropping the hook, we jump in the dinghy and head out to the reef where we snorke...
Sailing Bora Bora + Meet Chloe | Paradise at Sea
Sailing Doodles

Sailing Bora Bora + Meet Chloe | Paradise at Sea

We sail from one of the most beautiful bays we have ever spent the night in on the southeast side of Bora Bora and make our way around the island through the crystal-clear lagoon. Along the way we stop at the town dock to fill up on fresh water before grab...
This Might Be the Most Beautiful Sail on Earth (Bora Bora)
Sailing Doodles

This Might Be the Most Beautiful Sail on Earth (Bora Bora)

We leave the Bora Bora Yacht Club and sail around the island to the far side of Bora Bora—and it turns into one of the most breathtaking sails I’ve ever experienced. Unreal turquoise water, perfect conditions, and an anchorage that honestly might be th...
Before the Day Gets Going: Our Roles, Our Routine & a Fun Bikini Haul – The Lazy Geckos Ep. 341
Lazy Gecko Sailing & Adventures

Before the Day Gets Going: Our Roles, Our Routine & a Fun Bikini Haul – The Lazy Geckos Ep. 341

Meal preparation and so much more plays a crucial role in traveling on a sailboat. While Sundays are usually dedicated to family activities. today is different. We're pushing to prepare for the next passage! Then I'll take a few moments and show you some o...
Sailing to Bora Bora: Dolphins, Crystal Waters & Paradise
Sailing Doodles

Sailing to Bora Bora: Dolphins, Crystal Waters & Paradise

We set sail from Raiatea in French Polynesia and make the unforgettable journey to the legendary island of Bora Bora. With crystal-clear water, dramatic mountain peaks, and scenery that feels unreal, this is a place most people only dream of visiting. Afte...
SSL749 ~ The state of the Lady…
Captain Rick Moore

SSL749 ~ The state of the Lady…

Join our Patreon and join our Team SSL Crew! http://www.patreon.com/SailingSophisticatedLady Come and join us realtime at: http://www.facebook.com/groups/SSLBackstage http://www.instagram.com/SailingSophisticatedLady To all those contributing to our ne...
⛵️The FUTURE of JOCO: HALLBERG RASSY 44 BOAT TOUR | & taking apart the heat exchanger
Sailing Joco

⛵️The FUTURE of JOCO: HALLBERG RASSY 44 BOAT TOUR | & taking apart the heat exchanger

Joco's are movin on up!!! We live on a brand new HR44 ... for an afternoon :) But isn't she gorgeous!? Sure beats all the projects we have going on with Joco at the moment. Like taking apart the heat exchanger.... BOATLIFE Thank you for all your support!!...
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