Watch Sailing & Boating Adventures Around the World tagged “Caribbean” – Page 2 of 160

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 3840 results
SSL759 ~ Introducing our new SECRET WEAPON
Captain Rick Moore

SSL759 ~ Introducing our new SECRET WEAPON

Lots of things going on today, including the arrival of the first 3 of our new SECRET WEAPON solar panels onboard Sophisticated Lady! You all know we strive to run Sophisticated Lady entirely from solar power, so one of the main objectives of changing to ...
My $1.5M Catamaran STILL Isn’t Done…
Sailing Doodles

My $1.5M Catamaran STILL Isn’t Done…

My $1.5M electric catamaran is finally making progress… but somehow it still doesn’t look like it. In this episode I head back to the Island Spirit factory in Thailand for a full behind-the-scenes update on the build. It’s been a couple weeks since ...
SSL758 ~ 1st BIG surprise UNLEASHED !
Captain Rick Moore

SSL758 ~ 1st BIG surprise UNLEASHED !

Today we install our first of several new big surprise additions to Sophisticated Lady that will dramatically change/enhance her appearance.. we'll be installing a new radar antenna tower from SeaView Global marine systems! This one is designed to accommo...
SSL757 ~ Stage 2, Complete !
Captain Rick Moore

SSL757 ~ Stage 2, Complete !

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 Retire on Koh Chang? Week One Reality Check
Sailing Doodles

Could I Actually Retire on Koh Chang? Week One Reality Check

I spent a week on Koh Chang, Thailand to answer a real question: **could I actually retire here?** Not just visit for a few days—but really live here full-time without getting bored, running out of good restaurants, or feeling stuck on an island. In thi...
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...
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