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

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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!!...
Sailing French Polynesia: New Crew, New Boat, New Paradise
Sailing Doodles

Sailing French Polynesia: New Crew, New Boat, New Paradise

After a 15-hour flight halfway around the world, I finally arrive in French Polynesia — and it was worth every second. I charter a 40-foot Leopard catamaran and set off on an unforgettable 9-day sailing adventure through some of the most beautiful island...
The Last Sail: Why We Had to Leave the British Virgin Islands
Sailing Doodles

The Last Sail: Why We Had to Leave the British Virgin Islands

Today we wrap up an incredible week of sailing in the British Virgin Islands! ⛵🌴 We lifted anchor at Jost Van Dyke one last time and set a course toward Tortola’s beautiful West End. Soper’s Hole is one of the most colorful spots in the BVI, so w...
Perfect Day at Soggy Dollar… + Want to Join My Crew?
Sailing Doodles

Perfect Day at Soggy Dollar… + Want to Join My Crew?

Today we sail into one of the most iconic places in the entire BVI — White Bay on Jost Van Dyke, home of the world-famous Soggy Dollar Bar! It was a perfect beach day with the crew (even though I didn’t film a ton… we were having too much fun 😅). ...
Perfect Downwind Sail to Jost Van Dyke! | Bubbly Pool Adventure & Cane Garden Bay
Sailing Doodles

Perfect Downwind Sail to Jost Van Dyke! | Bubbly Pool Adventure & Cane Garden Bay

Today we had an absolutely perfect four-hour downwind sail from Anegada to Jost Van Dyke here in the beautiful British Virgin Islands. Conditions couldn’t have been better — blue water, steady breeze, and a happy crew enjoying every mile. Once we arri...
What Is The BEST Gun For Sailboat Self Defense?
Adventureman Dan

What Is The BEST Gun For Sailboat Self Defense?

What is the best firearm for self-defense on a sailboat in case of a piracy attack? As long as the weapon is legal to possess where you are: Handgun: Best for minimal space to stow &. But worst for accuracy and stopping power. I would most recommend a...
45-Foot Catamaran to Anegada | British Virgin Islands Sailing Adventure
Sailing Doodles

45-Foot Catamaran to Anegada | British Virgin Islands Sailing Adventure

Today we set sail from Virgin Gorda to the unique and beautiful island of Anegada — and it ended up being one of our fastest and most fun sails of the entire BVI trip. With perfect wind, flat seas, and the crew looking amazing on the bow, we made the cro...
BIKINI Workout While Sailing to THE BATHS!
Sailing Doodles

BIKINI Workout While Sailing to THE BATHS!

Start your day at Cooper Island, sail to one of the most iconic spots in the entire Caribbean, and wrap things up with a night you won’t forget. This was one of those PERFECT days in the BVI. We left Cooper Island early and made the short sail over to T...
⛵️SO DAMAGED! THRU HULL REPAIR DIY | Hallberg Rassy 352 | Tru Design
Sailing Joco

⛵️SO DAMAGED! THRU HULL REPAIR DIY | Hallberg Rassy 352 | Tru Design

LUCKY US - We found more damage to Joco! In this episode we complete the 4 thru hull replacements but find additional problems along the way - obviously. Spider cracks, blisters and what else....No matter, the JOCO's are on it and quickly so that we can ge...
BVI Magic: Stunning Crew Snorkels The Indians + 9-Knot Sail to Cooper Island!
Sailing Doodles

BVI Magic: Stunning Crew Snorkels The Indians + 9-Knot Sail to Cooper Island!

Day 2 sailing through the British Virgin Islands and it was absolutely perfect. This morning we left Norman Island and sailed over to The Indians, one of the most breathtaking snorkel sites in the entire BVI. The water was crystal clear, the coral was vibr...
Heartbreak Behind the Bikini… Dealing With Loss While Cruising – The Lazy Geckos Ep. 340
Lazy Gecko Sailing & Adventures

Heartbreak Behind the Bikini… Dealing With Loss While Cruising – The Lazy Geckos Ep. 340

Life on a boat involves unique challenges such as homeschooling while cruising, dealing with weather conditions, and managing solar power issues. The narrative reflects on the emotional toll of losing a family member while away from home. It also covers th...
New Crew, New Catamaran… and a Wild First Day in the BVI!
Sailing Doodles

New Crew, New Catamaran… and a Wild First Day in the BVI!

Join me as we kick off an incredible week-long sailing charter in the British Virgin Islands! We fly into the BVI to meet up with two new beautiful crew members and a returning favorite — Lauryn. After hopping aboard a brand-new Fountaine Pajot Elba 45, ...
The Last Sail of Nauti Dogs?
Sailing Doodles

The Last Sail of Nauti Dogs?

I’m sailing the boat down the East Coast for the final time before hauling her out of the water and storing her on land while the Nauti Dogs prize competition finishes up! In this episode I make the run from Atlantic City to Cape May, then across the De...
Sooo… We Got Busted Skinny Dipping 😅 – The Lazy Geckos Ep. 339
Lazy Gecko Sailing & Adventures

Sooo… We Got Busted Skinny Dipping 😅 – The Lazy Geckos Ep. 339

If you enjoy our videos, please SUBSCRIBE! Check out our webpage at www.thelazygeckos.com Other Links: Patreon: Become a Patreon at www.patreon.com/lazygeckos Instagram: Want more LGS? Follow our public Instagram @lazygeckosailing Follow Brittany's pe...
⛵️HOW TO STOP YOUR BOAT FROM SINKING | UNEXPECTED Thru Hull Replacement – TruDesign
Sailing Joco

⛵️HOW TO STOP YOUR BOAT FROM SINKING | UNEXPECTED Thru Hull Replacement – TruDesign

Here we go again with MORE HOLES in the boat! We're never going back in the water.... We discover some faulty Thru Hulls at the very last minute before launch and get busy QUICK to replace them. Only problem is we've never done it before Thank you for all...
Living on a Boat in Manhattan for a Week!
Sailing Doodles

Living on a Boat in Manhattan for a Week!

Docked right in the heart of Manhattan at the iconic Chelsea Piers Marina, I got to experience New York City like never before — from the deck of my sailboat! I launched the dinghy and cruised down the Hudson River, exploring the skyline and even making ...
Sailing Into New York City! Docking My Boat in the Heart of Manhattan
Sailing Doodles

Sailing Into New York City! Docking My Boat in the Heart of Manhattan

I sailed Nauti Dogs from Long Island Sound down the East River, under some of the most iconic bridges in the world, and right past the Manhattan skyline. From there, I rounded the southern tip of the island, cruised up the Hudson River, and docked right in...
SSL748 ~ Testing a BEAST!
Captain Rick Moore

SSL748 ~ Testing a BEAST!

Some of you might remember my other two sons, Justin and Brenden.. they are both on hand for todays video, and if you also remember that Brenden used to edit our SSL videos, you'll be happy to know that he edited todays video! Today we're having some fun ...
Sailing South for the Winter: Solo Leaving Block Island
Sailing Doodles

Sailing South for the Winter: Solo Leaving Block Island

After leaving Newport, Rhode Island, I set sail solo—just me and the dogs—toward Block Island. It’s one of the most beautiful spots on the East Coast, but when the weather turned, it became a wild few days riding out a storm at anchor. Once the skies...
Halloween Special! Our Spookiest Halloween Yet: We Slept in a Haunted Hotel Room! – The Lazy Geckos
Lazy Gecko Sailing & Adventures

Halloween Special! Our Spookiest Halloween Yet: We Slept in a Haunted Hotel Room! – The Lazy Geckos

We're staying in a HAUNTED MANSION that offers unique decor and handmade details. Adventure Suites in North Conway, NH features a flagship haunted castle room with asylum decor and jump scares. The hotel, rich in history, has been renovated by a family ove...
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