Watch Sailing & Boating Adventures Around the World tagged “Caribbean” – Page 2 of 160
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Showing 25-48 of 3827 results
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
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
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!)
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...
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
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
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…
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 !!
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
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
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
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
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
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
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...
SSL751 ~ A Potential new GAME CHANGER for SAILING ?
Today we are back in the boatyard with the ongoing re-fit of SOPHISTICATED LADY.. lots of projects on the go these days, including one today where we install a new set of Alpha Display Touchscreens from RayMarine, that are potentially a new GAME CHANGER fo...
Dutch vs French St. Martin: Cheap Lagoon Living… Then We LEFT
We explore Sint Maarten starting on the Dutch side — from planes screaming overhead at Maho Beach to cruising the surprisingly affordable liveaboard scene on Simpson Bay Lagoon. Living aboard here can be way cheaper than you might expect, and the vibe i...
Who Won My Boat?
The boat drawing is complete — and we have a winner. The drawing was done automatically, but the reserve was not met. As promised, that meant the winner would receive the partial cash equivalent of the funds raised rather than the boat itself. Right af...
⛵️PROVISIONING for 6 MONTHS SAILING the CARIBBEAN! How Much$$| Hallberg Rassy 352
WE ARE LEAVING ST MARTIN!!!!! But first - Provisioning Time. Come along and see a full day of shopping for random sh*t you never wanted to spend money on in the first place & we'll tell you how much it costs! Thank you for all your support!!! Busines...
Tiny Bikinis, Big Vibes | Wild Night in St. Barts
We kick things off soaking up the sun at Nikki Beach, easing into another unreal day in Saint Barthélemy. From there it’s poolside vibes, cold drinks, and Yosaira absolutely stealing the show in a tiny bikini that turns heads everywhere we go. That nig...
Anchored on an Uncharted Wreck… Then He Took Me Tubing While Mad 😳 – The Lazy Geckos Ep. 344
Join us as a fun day unfolds in the Bahamas with activities like snorkeling, tubing, and exploring a sunken wreck. The day highlights the joy of family bonding and adventure, concluding with reflections on creating lasting memories and preparing for their ...
SSL750 ~ Return to CHAOS…
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...
⛵️LEAVING THE BOATYARD BEHIND | New SAILING ADVENTURES begin NOW! (starting with seasick🤢)
We break FREE from the boatyard AND the lagoon to anchor out in crystal clear waters...FINALLY!!! It's been 13.5 months ON THE HARD and we don't quite have our sea legs yet and we get TOSSED around like rag dolls. But there is still work to be done so we ...
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