Watch Sailing & Boating Adventures Around the World tagged “Caribbean” – Page 2 of 158

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 25-48 of 3775 results
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...
Wasn’t Supposed to Be This Rough… Solo to Newport, RI
Sailing Doodles

Wasn’t Supposed to Be This Rough… Solo to Newport, RI

Start speaking a new language in 3 weeks with Babbel 🎉. Get up to 55% OFF your subscription ➡️ Here: https://bit.ly/SailingDoodlesOct I set sail solo from Bridgeport, Connecticut, heading for Newport, Rhode Island — expecting a calm run up the co...
SSL747 ~ Time for a MAJOR Change
Captain Rick Moore

SSL747 ~ Time for a MAJOR Change

We're off on a new kind of adventure this time, and not sure how long it will last because life is moving in directions we never anticipated.. that ever happen to you?? Thanks for your support of our journey, and hope you enjoy this latest episode in o...
Sailing Croatia with 4 Beautiful Crew | 1.5 Hour Adventure Film
Sailing Doodles

Sailing Croatia with 4 Beautiful Crew | 1.5 Hour Adventure Film

Join me and an incredible all-female crew of four as we charter a luxury catamaran to explore the jaw-dropping Croatian coast. For seven unforgettable days, we sail from Split to the islands of Hvar, Vis, and Korčula — crystal blue water, hidden coves,...
Organized Chaos: 100 Boats Depart the Annapolis Boat Show!
Sailing Doodles

Organized Chaos: 100 Boats Depart the Annapolis Boat Show!

The Annapolis Boat Show is over, but the real work begins! At sunrise, I head back to the docks to help with the massive teardown — floating docks are being dismantled, crews are casting off lines, and nearly 100 boats start departing in a well-orchestra...
SSL746 ~ time to say Good-Bye
Captain Rick Moore

SSL746 ~ time to say Good-Bye

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...
Welcome back LAURA!  With her two kids!
Sailing Doodles

Welcome back LAURA! With her two kids!

Laura — one of the original Sailing Doodles crew and a fan favorite — joins me in Annapolis for a special reunion! This time, she’s brought her two kids along for the adventure. We head to the Annapolis Boat Show, where I show her the brand-new Isla...
Sailing for Remote Islands! – The Lazy Geckos Ep. 337
Lazy Gecko Sailing & Adventures

Sailing for Remote Islands! – The Lazy Geckos Ep. 337

We're off to search for a private beach! We'll overcome some personal issues we're having and get that watermaker going! Then an adventure in a lagoon offers a refreshing break before we're sailing away again! If you enjoy our videos, please SUBSCRIBE! C...
⛵️More BOATS & HOLES! | Genoa Track Install, CORE SAMPLE & …HOLES | Hallberg Rassy 352 MAJOR Refit
Sailing Joco

⛵️More BOATS & HOLES! | Genoa Track Install, CORE SAMPLE & …HOLES | Hallberg Rassy 352 MAJOR Refit

Another episode & more boat work! Are you sick of it yet? CUZ WE ARE! lol. Only a few more boatyard episodes to go before we splash so let's get these projects finished! Thank you for all your support!!! Business/Collab Inquiries [email protected] ...
SSL745 ~ DISMASTED
Captain Rick Moore

SSL745 ~ DISMASTED

Today's update takes us back to the boat in Cartegana, COLOMBIA, on the hard at Manzanilo Marina and Boatyard.. we spend time reviewing some of the recent issues we've found with the hull and keel bolts of "Sophisticated Lady".. and hopefully find solution...
My NEW Yacht Has Arrived! Delivering It to the Annapolis Boat Show
Sailing Doodles

My NEW Yacht Has Arrived! Delivering It to the Annapolis Boat Show

The long-awaited Island Spirit 525e hybrid-electric catamaran has finally made it to the U.S.! Hull #3 just arrived in Maryland, and since I’m getting Hull #5, I jumped aboard to help deliver her to the Annapolis Boat Show for her worldwide debut. Come ...
Boat Life Burnout Is Real — This Mom Needs Some Free Time at Atlantis!! – The Lazy Geckos Ep. 336
Lazy Gecko Sailing & Adventures

Boat Life Burnout Is Real — This Mom Needs Some Free Time at Atlantis!! – The Lazy Geckos Ep. 336

Welcome to Atlantis!! We're taking a break after several weeks on the hook! We've decided to pull into a fancy, Mega-Yacht marina and enjoy all this lovely destination has to offer! If you enjoy our videos, please SUBSCRIBE! Check out our webpage at www...
⛵️WE BOUGHT A NEW DINGHY! (for HOW MUCH?!) | Hallberg Rassy 352 | The Cost of Cruising
Sailing Joco

⛵️WE BOUGHT A NEW DINGHY! (for HOW MUCH?!) | Hallberg Rassy 352 | The Cost of Cruising

Let's find the BEST DEAL IN THE CARIBBEAN! You KNOW we've done our research when it comes to spending a huge chunk of $$ so come along as we shop for a new "car"!! First Tip: Buy in a country where there are no taxes :) Thank you for all your support!!! ...
The Ghost Crew: Sailing With Faces I Couldn’t Show
Sailing Doodles

The Ghost Crew: Sailing With Faces I Couldn’t Show

We set sail from Port Washington to Huntington Bay, Long Island — a beautiful day on the water with two amazing crew members. But after the trip, they asked not to appear in the video… so I had to blur them out. It turned into one of the most challengi...
SSL744 ~ Can a portable ECOFLOW Delta 2 Max power an AIR CONDITIONER ?
Captain Rick Moore

SSL744 ~ Can a portable ECOFLOW Delta 2 Max power an AIR CONDITIONER ?

Question I've been asked by a lot of you.. can one of these portable solar generator/power stations actually power an Air Conditioner..? Well, today we're going to find out as I run a couple of high power capacity tests on a new EcoFlow Delta 2 Max expand...
Giving Away My Sailboat to One of You!
Sailing Doodles

Giving Away My Sailboat to One of You!

🎉 BIG ANNOUNCEMENT – I’m giving away my sailboat, and YOU could be the new owner! ⚓️ This is your chance to win "SV Nauti Dogs" a 1989 Ta Chiao CT-56 bluewater cruiser, the yacht that has taken me on so many incredible adventures. Instead of se...
Boat Life Balance: Work Hard, Relax Harder – The Lazy Geckos Ep. 335
Lazy Gecko Sailing & Adventures

Boat Life Balance: Work Hard, Relax Harder – The Lazy Geckos Ep. 335

Life on our boat includes daily tasks such as making water and preparing meals afloat, we'll walk you through the process! Provisioning for these trips is also challenging, especially with grocery shopping and managing currency in a new country. We're goin...
Epic water experiences, one click away.

Something AWESOME is coming!
Be the FIRST to know⛵

Sign up for exclusive updates and be the first to hear when we go live!
Get sneak peeks, exciting announcement, and special content straight to your inbox!

We don’t spam! Read our privacy policy for more info.


WeBoating
Logo
Shopping cart