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

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I Met Her Yesterday… Now She’s Sailing With Me
Sailing Doodles

I Met Her Yesterday… Now She’s Sailing With Me

I met Olivia on Bumble, and she was supposed to fly home to Poland today… but somehow I talked her into skipping her flight and coming sailing with me instead. Before we head out, I wanted to take her to the Island Spirit factory here in Thailand and gi...
SSL767 ~ Installing and testing the new SHADE TOLERANT flexible TopCon solar panels from BougeRV
Captain Rick Moore

SSL767 ~ Installing and testing the new SHADE TOLERANT flexible TopCon solar panels from BougeRV

After many months in the design stage, we are finally ready to install and test our new SECRET WEAPON.. our new Flexible fiberglass TopCon Arch Pro 200 watt solar panels from BougeRV.. in fact, we are installing 12 of them for a total output power rating o...
She’s Catching Rays…He’s Catching Problems – The Lazy Geckos Ep. 350
Lazy Gecko Sailing & Adventures

She’s Catching Rays…He’s Catching Problems – The Lazy Geckos Ep. 350

Follow the installation and commissioning of a new Blue Water Voyager watermaker aboard Calypso. This comprehensive video details the process, from initial setup and troubleshooting to achieving optimal performance. Witness the team's dedication as they ov...
SSL766 ~ Can’t go anywhere…
Captain Rick Moore

SSL766 ~ Can’t go anywhere…

Help us get Riccardo Jr into the finals for the Ranger Rick Jr Ranger competition.. he's almost there.. you guys helped him move from #11 to #2 last month so he is now in the semi-finals, but he's slipped down to #3 as competition is fierce.. lets see if w...
I Found the Island I Want to Retire On in Thailand
Sailing Doodles

I Found the Island I Want to Retire On in Thailand

I’ve traveled all over Thailand, but there’s one island that keeps standing out to me: Koh Chang. In this episode, I take the truck on a 5-hour road trip across Thailand, hop on the ferry, and head over to the island that I could honestly see myself r...
⛵️BOAT LIFE: Sailing & ENGINE MAINTENANCE TIME!
Sailing Joco

⛵️BOAT LIFE: Sailing & ENGINE MAINTENANCE TIME!

Come with us on a typical Boat Life Day - Sailing to New Tropical Places...TO DO BOAT WORK! :) Thank you for all your support!!! Business/Collab Inquiries [email protected] If you’re enjoying our content, please consider Joining Our Patreon! We appr...
My New Boat Was Damaged… 12 Days Before Launch!
Sailing Doodles

My New Boat Was Damaged… 12 Days Before Launch!

My new Island Spirit 525 electric catamaran is finally getting close to leaving the factory! In this episode, I head back to the Island Spirit factory in Thailand to check on the progress of my boat build, and it looks like we are only about 12 days away f...
Bad News About My New Boat… Again
Sailing Doodles

Bad News About My New Boat… Again

We spent our last day aboard the Island Spirit 525e charter boat, making the most of a beautiful day on the water before sailing her back to the marina. We hit the beach, enjoyed one last cruise, and the girls soaked up the sun before heading home. But af...
SSL765 ~ Uh oh… What happens next ?!?
Captain Rick Moore

SSL765 ~ Uh oh… What happens next ?!?

YES, it's FINALLY LAUNCH DAY... Yaaayyy! It's been a long haul but today 'Sophisticated Lady' finally made it back in the water, after 6 months of solid time spent refitting her, she is finally ready to stretch her legs on the ocean again... almost... Jo...
Back to Ao Po… Where My Boat Dragged Anchor
Sailing Doodles

Back to Ao Po… Where My Boat Dragged Anchor

In this episode of Sailing Doodles, we explore some of the most famous spots in Phang Nga Bay, Thailand. We begin in the floating village of Koh Panyi, where we hire a traditional Thai longtail boat and head through the mangroves and sea caves. Then we sai...
My Boat Isn’t Ready… So We Took This One Instead
Sailing Doodles

My Boat Isn’t Ready… So We Took This One Instead

We’re still a few weeks away from my own Island Spirit 525 being ready, so instead of sitting around waiting, we head to Phuket and jump aboard Island Spirit 525 Hull 4 for an amazing sailing adventure. In this video, I give you a full tour of the boat ...
SSL764 ~ yet ANOTHER delay..
Captain Rick Moore

SSL764 ~ yet ANOTHER delay..

This was such an amazing day, I can't even begin to explain.. special thanks to our friend Juan Carlos for the anniversary gift of a helicopter tour around Cartagena Harbor, it was truly a special moment for all of us, including Ricci! If you are in the a...
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...
SSL763 ~ Well, we ALMOST made it…
Captain Rick Moore

SSL763 ~ Well, we ALMOST made it…

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...
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...
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