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

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Goodbye Chloe… Hello New Crew | Thailand Road Trip to Hua Hin & Phuket
Sailing Doodles

Goodbye Chloe… Hello New Crew | Thailand Road Trip to Hua Hin & Phuket

Thanks to CyberGhost for supporting this video! Head over to sign up and get yourself protected today! https://cyberghostvpn.com/SailingDoodles This one is full of big changes… We hit the road from Pattaya to Hua Hin, one of the places I could actually...
We Ditched Our Watermaker…Here’s Why – The Lazy Geckos Ep. 349
Lazy Gecko Sailing & Adventures

We Ditched Our Watermaker…Here’s Why – The Lazy Geckos Ep. 349

We've had it! After years of rebuilds, failing on us at the worst possible times, we've torn the Spectra Watermaker out of Calypso and are going with a new brand! We'll also get the new trampolines in and get them installed! Car Seat Info: 🛒 Travel C...
⛵️Sailing (on purpose) to an ACTIVE VOLCANO🌋 | Hallberg Rassy 352
Sailing Joco

⛵️Sailing (on purpose) to an ACTIVE VOLCANO🌋 | Hallberg Rassy 352

Three thousand years ago, following a large pumice eruption, the Étang Sec (French for Dry Pond) caldera was then formed. The 1902 eruption took place within the Étang Sec crater. This eruption formed many pyroclastic flows and produced a dome that fille...
Unexpected Powerboat Races in Thailand! Sailing from Koh Sichang to Monkey Island
Sailing Doodles

Unexpected Powerboat Races in Thailand! Sailing from Koh Sichang to Monkey Island

After two nights at anchor at Koh Sichang near Pattaya, we pull up anchor and sail back toward mainland Thailand. Just south of Pattaya, we find a beautiful anchorage and head ashore, only to discover we’ve landed in the middle of an unexpected powerboat...
SSL762 ~ the BIGGEST surprise you NEVER saw coming…
Captain Rick Moore

SSL762 ~ the BIGGEST surprise you NEVER saw coming…

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...
I Got Sick in Thailand… So Chloe Took Over
Sailing Doodles

I Got Sick in Thailand… So Chloe Took Over

After a peaceful night at anchor off Koh Larn, we woke up to the bay filling with jet skis and tour boats, so it was time to move on. Unfortunately, I was already feeling terrible from something I ate the night before. We got the boat underway and made th...
SSL761 ~ Our little Ricci needs your HELP
Captain Rick Moore

SSL761 ~ Our little Ricci needs your HELP

If you want to help our little Ricci qualify for the Ranger Rick Jr Ranger competition, please find the link below.. https://jr-ranger.org/2026/riccardo-1ecb But be advised, it is a Facebook link, so if you are already logged in to your Facebook profile...
This Brand New Catamaran Isn’t Mine… But I Took It Anyway
Sailing Doodles

This Brand New Catamaran Isn’t Mine… But I Took It Anyway

After months of waiting for my new catamaran… I finally got out on the water. The team at Island Spirit handed me the keys to their brand new 410 catamaran for a full shakedown cruise here in Thailand — and I couldn’t wait to see what it could do. ...
SSL760 ~ our 2nd BIG SURPRISE
Captain Rick Moore

SSL760 ~ our 2nd BIG SURPRISE

Stage 2 of our major transformation in the appearance of Sophisticated Lady involves a full wrap of 3M pearlescent white color shifting vinyl that will reflect the colors of a seashell when in the sun.. blues, pinks, greens, turquiose, they're all there! ...
Delivery Day… But My Boat Still Isn’t Ready 😬
Sailing Doodles

Delivery Day… But My Boat Still Isn’t Ready 😬

I showed up expecting my new $1.5M electric catamaran to be finished… but something wasn’t right. The boat looks nearly complete — and honestly, it’s incredible to see how far it’s come. In this video, I take you inside the Island Spirit factory...
I Don’t Even Know Where to Start! New Season, New Problems! The Lazy Geckos – Ep. 348
Lazy Gecko Sailing & Adventures

I Don’t Even Know Where to Start! New Season, New Problems! The Lazy Geckos – Ep. 348

The first episode of Season 14! We're back onboard after a few months away and are busy getting Calypso set up to cruise! We'll find out what condition she's in from sitting still and we'll get those trampolines started! Check out our webpage at www.thela...
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!!...
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