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

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SSL756 ~ a very BIG moment !
Captain Rick Moore

SSL756 ~ a very BIG moment !

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...
Could I Actually Live Here? (Thailand Test Week 🇹🇭)
Sailing Doodles

Could I Actually Live Here? (Thailand Test Week 🇹🇭)

On our final day aboard the Lagoon 400 in Thailand, we sail back to the charter base and say goodbye to an incredible week on the water. But the adventure doesn’t stop there… Koh Chang has been on my radar as a potential place to spend more time — ...
$15 Beach Bungalows in Thailand?! (Sailing Into a Storm)
Sailing Doodles

$15 Beach Bungalows in Thailand?! (Sailing Into a Storm)

We woke up anchored off Ao Salat on Koh Kood after one of the calmest nights we’ve had in Thailand. From there, we pulled anchor and set sail 18 miles north toward Koh Wai… with a thunderstorm building right in our path. After dodging the weather, we ...
The Next Chapter Starts NOW!  – The Lazy Geckos Season 14
Lazy Gecko Sailing & Adventures

The Next Chapter Starts NOW! – The Lazy Geckos Season 14

In this season, we're upgrading our sailing catamaran and we're sailing through the islands! Come along for all the fun! Check out our webpage at www.thelazygeckos.com Other Links: Patreon: Become a Patreon at www.patreon.com/lazygeckos Instagram: Want...
WHERE IS THIS? #sailing
The Cruising Kiwis
SSL755 ~ Finally.. time for COPPERCOAT !!
Captain Rick Moore

SSL755 ~ Finally.. time for COPPERCOAT !!

Today is a big day for SOPHISTICATED LADY.. After 4+ Years of thinking and planning, we finally have our CopperCoat package ready to apply! The preparation work is all laid out, the guys are ready, the CopperCoat is READY.. time for a new copper infused ...
We Found a Hidden Village Built Over the Ocean in Thailand
Sailing Doodles

We Found a Hidden Village Built Over the Ocean in Thailand

Today we explore one of the most unique places we've discovered while sailing in Thailand. We start the morning anchored off Bang Bao on Koh Kood, heading ashore in search of breakfast at a beautiful beachfront resort. Unfortunately… no luck. So we rais...
⛵️SAILING Guadeloupe | Check In …or CHECK OUT?! | Hallberg Rassy 352
Sailing Joco

⛵️SAILING Guadeloupe | Check In …or CHECK OUT?! | Hallberg Rassy 352

In today's episode we visit an anchorage WELL KNOWN for Death In Paradise... we scramble around the village to check-in to the country but how long will we survive? Oh and we show you grocery shopping too :) lol the drama Thank you for all your support!!...
I Think I Want to Move to This Island in Thailand
Sailing Doodles

I Think I Want to Move to This Island in Thailand

We woke up to an incredibly calm morning anchored in a beautiful bay at Koh Mak, Thailand. With the water like glass and the jungle surrounding us, it was the perfect start to the day. After taking the dinghy ashore, Chloe and I went exploring through the...
SSL754 ~ Captain’s Update – March 11th
Captain Rick Moore

SSL754 ~ Captain’s Update – March 11th

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...
SSL753 ~ Captain’s Update – March 8th
Captain Rick Moore

SSL753 ~ Captain’s Update – March 8th

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...
Sailing Thailand! Lagoon 400 Day Sail to Koh Mak (With the Dogs!)
Sailing Doodles

Sailing Thailand! Lagoon 400 Day Sail to Koh Mak (With the Dogs!)

Today’s adventure starts with a 5 hour road trip from Pattaya down to Koh Chang, where we jump aboard a Lagoon 400 catamaran for a beautiful sail through the islands of eastern Thailand. After a quick tour of the boat, we untie the lines and head out fo...
DISCOVERING TRINIDAD WITH CATS AND DOGS
The Cruising Kiwis
Every Voyage Must End… – The Lazy Geckos Ep. 347
Lazy Gecko Sailing & Adventures

Every Voyage Must End… – The Lazy Geckos Ep. 347

Join us as we navigate the final leg of our Bahamas shakedown cruise aboard Calypso. Facing necessary upgrades and repairs, we'll prepare to re-enter US waters, discuss the challenges of cruising with a baby and address Jeremiah's health concerns. We'll a...
Should I buy this instead? Island Spirit 410 Tour
Sailing Doodles

Should I buy this instead? Island Spirit 410 Tour

Should I buy the Island Spirit 410 instead of my new 525? 🤔 In this video I take you aboard the Island Spirit 410, the smaller sister ship to the Island Spirit 525e catamaran currently being built for me here in Thailand. At first glance it’s a serio...
⛵️SAILING (off anchor) to GUADELOUPE at Sunrise! | Hallberg Rassy 352
Sailing Joco

⛵️SAILING (off anchor) to GUADELOUPE at Sunrise! | Hallberg Rassy 352

Good morning everyone! Antigua has been a blast, but our short and sweet time here has passed and at sunrise we sail off anchor towards Guadeloupe. Come with us ! Thank you for all your support!!! Business/Collab Inquiries [email protected] If you’re...
FIRST Look at Our New $1.5M Catamaran! It’s Almost Ready…
Sailing Doodles

FIRST Look at Our New $1.5M Catamaran! It’s Almost Ready…

It’s finally happening. After months of planning and waiting, we arrive in Thailand to see our brand-new catamaran for the very first time. But first… we had to get the dogs there safely — which meant flying them cargo to Bangkok. In this episode:...
SSL752 ~ Totally CRAZY !!
Captain Rick Moore

SSL752 ~ Totally CRAZY !!

If you would like to help me support my family's efforts to help families in need, here is the link, and thank-you so much! https://www.canadahelps.org/en/dn/122435?qrcode=1 Join our Patreon and join our Team SSL Crew! http://www.patreon.com/SailingSophis...
We Partied on the WORLD’S LARGEST Cruise Ship! | Groove Cruise 2026
Sailing Doodles

We Partied on the WORLD’S LARGEST Cruise Ship! | Groove Cruise 2026

We just experienced one of the wildest events we’ve ever seen… Groove Cruise 2026 — a full-blown music festival… on one of the largest cruise ships in the world. For 4 nights we sailed from Miami to Nassau and back aboard the incredible Royal Car...
Pitch Black. Open Ocean. Gulf Stream Crossing. – The Lazy Geckos Ep. 346
Lazy Gecko Sailing & Adventures

Pitch Black. Open Ocean. Gulf Stream Crossing. – The Lazy Geckos Ep. 346

Early morning starts with our crew preparing for a Gulf Stream crossing. We'll check equipment, discuss conditions, and pull up the anchor. Navigating through changing depths, we'll monitor the radar and more in pitch black conditions! We'll also express ...
SAIL TO ANTIGUA
Adventures of an old Seadog

SAIL TO ANTIGUA

Back in the Caribbean !! Thanks you for watching this episode, please give us a thumbs up and subscribe. Don't forget to click the bell next to the subscribe button to notify you of every new episode, that way you’ll never miss an adventure!! Also checko...
⛵️OUR FIRST SAIL (overnight) AFTER 395 DAYS in the BOATYARD | Hallberg Rassy 352
Sailing Joco

⛵️OUR FIRST SAIL (overnight) AFTER 395 DAYS in the BOATYARD | Hallberg Rassy 352

WERE ON THE MOVE! Finally wow ...frick... Our FIRST SAIL in over a year is fully documented, the good bad and squally :) Thank you for all your support!!! Business/Collab Inquiries [email protected] If you’re enjoying our content, please consider Jo...
Party’s Over… Last Day in St. Martin
Sailing Doodles

Party’s Over… Last Day in St. Martin

It’s our final day of this catamaran sailing charter in St. Martin… and we’re going out the right way. We drop anchor off the stunning beach in Grand Case, spend the afternoon dancing in the sand in front of the iconic Rainbow Café, and soak up eve...
You Wouldn’t Believe How HOT It Gets! – The Lazy Geckos Ep. 345
Lazy Gecko Sailing & Adventures

You Wouldn’t Believe How HOT It Gets! – The Lazy Geckos Ep. 345

Today we'll face thunderstorms while preparing for a long sailing passage. Brittany will discuss cooking onboard and managing kids amidst the heat, encountering challenges with both. Emphasizing the need for breaks and hydration, we'll reflect on our journ...
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