Watch Sailing & Boating Adventures Around the World tagged “Caribbean” – Page 2 of 157

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 3760 results
⛵️More BOATS & HOLES! | Genoa Track Install, CORE SAMPLE & …HOLES | Hallberg Rassy 352 MAJOR Refit
Sailing Joco

⛵️More BOATS & HOLES! | Genoa Track Install, CORE SAMPLE & …HOLES | Hallberg Rassy 352 MAJOR Refit

Another episode & more boat work! Are you sick of it yet? CUZ WE ARE! lol. Only a few more boatyard episodes to go before we splash so let's get these projects finished! Thank you for all your support!!! Business/Collab Inquiries [email protected] ...
SSL745 ~ DISMASTED
Captain Rick Moore

SSL745 ~ DISMASTED

Today's update takes us back to the boat in Cartegana, COLOMBIA, on the hard at Manzanilo Marina and Boatyard.. we spend time reviewing some of the recent issues we've found with the hull and keel bolts of "Sophisticated Lady".. and hopefully find solution...
My NEW Yacht Has Arrived! Delivering It to the Annapolis Boat Show
Sailing Doodles

My NEW Yacht Has Arrived! Delivering It to the Annapolis Boat Show

The long-awaited Island Spirit 525e hybrid-electric catamaran has finally made it to the U.S.! Hull #3 just arrived in Maryland, and since I’m getting Hull #5, I jumped aboard to help deliver her to the Annapolis Boat Show for her worldwide debut. Come ...
Boat Life Burnout Is Real — This Mom Needs Some Free Time at Atlantis!! – The Lazy Geckos Ep. 336
Lazy Gecko Sailing & Adventures

Boat Life Burnout Is Real — This Mom Needs Some Free Time at Atlantis!! – The Lazy Geckos Ep. 336

Welcome to Atlantis!! We're taking a break after several weeks on the hook! We've decided to pull into a fancy, Mega-Yacht marina and enjoy all this lovely destination has to offer! If you enjoy our videos, please SUBSCRIBE! Check out our webpage at www...
⛵️WE BOUGHT A NEW DINGHY! (for HOW MUCH?!) | Hallberg Rassy 352 | The Cost of Cruising
Sailing Joco

⛵️WE BOUGHT A NEW DINGHY! (for HOW MUCH?!) | Hallberg Rassy 352 | The Cost of Cruising

Let's find the BEST DEAL IN THE CARIBBEAN! You KNOW we've done our research when it comes to spending a huge chunk of $$ so come along as we shop for a new "car"!! First Tip: Buy in a country where there are no taxes :) Thank you for all your support!!! ...
The Ghost Crew: Sailing With Faces I Couldn’t Show
Sailing Doodles

The Ghost Crew: Sailing With Faces I Couldn’t Show

We set sail from Port Washington to Huntington Bay, Long Island — a beautiful day on the water with two amazing crew members. But after the trip, they asked not to appear in the video… so I had to blur them out. It turned into one of the most challengi...
SSL744 ~ Can a portable ECOFLOW Delta 2 Max power an AIR CONDITIONER ?
Captain Rick Moore

SSL744 ~ Can a portable ECOFLOW Delta 2 Max power an AIR CONDITIONER ?

Question I've been asked by a lot of you.. can one of these portable solar generator/power stations actually power an Air Conditioner..? Well, today we're going to find out as I run a couple of high power capacity tests on a new EcoFlow Delta 2 Max expand...
Giving Away My Sailboat to One of You!
Sailing Doodles

Giving Away My Sailboat to One of You!

🎉 BIG ANNOUNCEMENT – I’m giving away my sailboat, and YOU could be the new owner! ⚓️ This is your chance to win "SV Nauti Dogs" a 1989 Ta Chiao CT-56 bluewater cruiser, the yacht that has taken me on so many incredible adventures. Instead of se...
Boat Life Balance: Work Hard, Relax Harder – The Lazy Geckos Ep. 335
Lazy Gecko Sailing & Adventures

Boat Life Balance: Work Hard, Relax Harder – The Lazy Geckos Ep. 335

Life on our boat includes daily tasks such as making water and preparing meals afloat, we'll walk you through the process! Provisioning for these trips is also challenging, especially with grocery shopping and managing currency in a new country. We're goin...
SSL743 ~ some very bad news…
Captain Rick Moore

SSL743 ~ some very bad news…

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 NYC with Emma from Flying Doodles! | East River to Long Island Sound
Sailing Doodles

Sailing NYC with Emma from Flying Doodles! | East River to Long Island Sound

We set sail right through the heart of New York City! Emma, the host of Flying Doodles, and her boyfriend join me on Nauti Dogs as we cruise past Manhattan, up the East River, and into the Long Island Sound. We make it to Port Washington, where Emma and he...
⛵️from THIS to THIS! | Teak Deck/RudderRepair/Paint/TOILETS! | Hallberg Rassy 352 Sailboat REFIT
Sailing Joco

⛵️from THIS to THIS! | Teak Deck/RudderRepair/Paint/TOILETS! | Hallberg Rassy 352 Sailboat REFIT

WOW this has been a TRIP guys! We're nearing the end of our ONE YEAR REFIT with final touches being done on the topsides, interior upgrades & below the waterline repairs. We are so thankful to have all of you continuing to cheer us along for every mile...
Sailing Italy’s Amalfi Coast: Naples to Capri (Full Journey Documentary)
Sailing Doodles

Sailing Italy’s Amalfi Coast: Naples to Capri (Full Journey Documentary)

Join us for an unforgettable sailing adventure along Italy’s Amalfi Coast and surrounding islands. Starting from Naples, we cruise through the colorful fishing villages of Procida, soak in the hot springs of Ischia, sail past the dramatic cliffs of Capri...
Goodbye Lauryn, Hello Emma | Sailing to NYC & Aerial Hoop Show at the Statue of Liberty
Sailing Doodles

Goodbye Lauryn, Hello Emma | Sailing to NYC & Aerial Hoop Show at the Statue of Liberty

We set sail from Atlantic City for our final leg with Lauryn, heading up the coast to New York City. The sail takes us right past the Statue of Liberty before we dock in Brooklyn, where it’s time to say goodbye to Lauryn… and hello to Emma from @Flying...
SSL742 ~ a very BIG hole in the Boat
Captain Rick Moore

SSL742 ~ a very BIG hole in the Boat

More projects with our refit today as we tackle some old thru-hulls that are way overdue for replacement.. including the mounting of our new 3D sonar transducer with a sneak peak at one of our next major upgrades from RayMarine for Sophisiticated Lady... t...
SSL741 ~ Testing the BRAND NEW Bluetti RV Solar 48V Power System
Captain Rick Moore

SSL741 ~ Testing the BRAND NEW Bluetti RV Solar 48V Power System

Learn more about the BRAND NEW Bluetti RV5 Off-Grid Energy System at: http://bit.ly/3V5wM4Q If you are interested to order one, use code: Rick5off to save an extra 5% off sitewide BLUETTI RVSolar 48V Power System: http://bit.ly/4pa4TWW Join our Patre...
TRAPPED in a rough anchorage & a Sweet Escape! – The Lazy Geckos Ep. 334
Lazy Gecko Sailing & Adventures

TRAPPED in a rough anchorage & a Sweet Escape! – The Lazy Geckos Ep. 334

We'll experience more excitement at sea including dealing with thunderstorms and challenges in our anchorage due to wind and swell. We'll plan along with you to wait for better weather before moving. Then we're on an offshore passage where we'll catch a SW...
The HOTTEST SAILOR on the YouTube
Sailing Doodles

The HOTTEST SAILOR on the YouTube

@Lost_Lauryn is probably the most beautiful sailing on youtube today! We have engine problems as soon as we pull up anchor at Cape May and we are drifting with the wind and current. I take quick action to get the motor started and then we sail 40 miles u...
We Sailed From Freezing To Bikini Weather In One Day!
Sailing Doodles

We Sailed From Freezing To Bikini Weather In One Day!

We set sail at dawn from the C&D Canal bundled up in the morning chill, but by midday it turned into perfect bikini weather! With a steady breeze at our backs, we enjoyed an epic downwind run down Delaware Bay and made landfall in Cape May, New Jersey....
Ep. 78 Line guides and rabbit feast
SAILING into FREEDOM

Ep. 78 Line guides and rabbit feast

Give it a thumbs up if you liked this episode! Get your Sailing Into Freedom Crew T-shirt: https://teespring.com/stores/sailing-into-freedom Want more? Became our patron and get access to exclusive content. https://www.patreon.com/sailingintofreedom If ...
SSL739 ~ we NEVER expected THIS..!
Captain Rick Moore

SSL739 ~ we NEVER expected THIS..!

If you'd like to see more about Clara and Hubert, our best crew ever, find their Instagram page at: http://www.instagram.com/morrisandlea and be sure and tell them we said Hi! :) Our friend Roxanne also does private bookings for her music anywhere in the...
Haul Out Prep on Panama’s Caribbean Coast (the countdown is on) | Sailing Sitka Ep 185
Sailing Sitka

Haul Out Prep on Panama’s Caribbean Coast (the countdown is on) | Sailing Sitka Ep 185

As Jay and Kenna spend their final week at anchor in Linton Bay, Panama, they prepare their Cheoy Lee Offshore 41’ for life on the hard. It’s never easy saying goodbye to this chapter—long days of work, tough decisions, and the bittersweet feeling of...
Best Boats at Newport Boat Show 2025 | Hylas, Beneteau & Lagoon
Sailing Doodles

Best Boats at Newport Boat Show 2025 | Hylas, Beneteau & Lagoon

Join me at Day One of the Newport International Boat Show 2025! I dive into the latest electric motor technology and tour some incredible yachts, including: Hylas 57 – luxury bluewater cruiser Kufner 57 – sleek performance yacht Beneteau Swift Trawl...
SSL739 ~ a LASER for our REFIT ??
Captain Rick Moore

SSL739 ~ a LASER for our REFIT ??

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...
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