Watch Sailing & Boating Adventures Around the World tagged “Caribbean”
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.
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...
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...
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...
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’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...
Come with us on a typical Boat Life Day - Sailing to New Tropical Places...TO DO BOAT WORK! :)
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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...
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...
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...
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...
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 ...
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...
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This one is full of big changes…
We hit the road from Pattaya to Hua Hin, one of the places I could actually...
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Come and join us realtime at:
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To all those contributing to our ne...
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...
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...
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...
Join our Patreon and join our Team SSL Crew!
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Come and join us realtime at:
http://www.facebook.com/groups/SSLBackstage
http://www.instagram.com/SailingSophisticatedLady
To all those contributing to our ne...
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...
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...
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.
...
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! ...
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...
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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