Watch Sailing & Boating Adventures Around the World tagged “Sailing caribbean” – Page 4 of 35

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.

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The AMAZING DEAL Boat to Buy in 2025 – Jeanneau Sun Odyssey 37 vs Catalina 380 vs Beneteau 37.1
Lady K Sailing

The AMAZING DEAL Boat to Buy in 2025 – Jeanneau Sun Odyssey 37 vs Catalina 380 vs Beneteau 37.1

Sailboat shopping? Want to get the best bang for your buck on a cruising sailboat in 2025? The Catalina 380 was all the rage in cheap sailboats but, they're hard to find now. The Beneteau uses glued in keel matrix strigners that can lead to keel failure. T...
NOTHING’S CHANGED – Except Our Minds | SailAway 298
SailAway World Sailing

NOTHING’S CHANGED – Except Our Minds | SailAway 298

If there's anything the SAILING LIFE has taught us, it's how to PIVOT. We've made a lot of BIG DECISIONS through the years, but likely none AS BIG as THIS ONE. We can only hope it's the RIGHT decision and plow forward FULL STEAM. Enjoy!! And be sure to...
Greatest Sailing Adventure Movie Ever! Lady K Sailing – Ep 309
Lady K Sailing

Greatest Sailing Adventure Movie Ever! Lady K Sailing – Ep 309

In 2008, a farm boy from Indiana named Alex Rust was working at The Chicago Board of Trade. He found success, but not happiness. At the age of 25 Alex quit his job and drove to Florida in search of something better. He traded his old minivan for a small sa...
Here’s To HOPIN’ Our Boat’s Still FLOATIN’! | SailAway 297
SailAway World Sailing

Here’s To HOPIN’ Our Boat’s Still FLOATIN’! | SailAway 297

A MONTH! By far the longest we've ever left Ophelia AND IN THE WATER to boot. Even with good friends keeping an eye out, there's no telling what issues may have developed while we were gone. After a LAST GASP of fun with our families and friends, it's t...
Dangerous Sailboat Myths Busted! Ep 308 – Lady K Sailing
Lady K Sailing

Dangerous Sailboat Myths Busted! Ep 308 – Lady K Sailing

How to sail safely is a complicated topic and which sailboat to buy really depends on what you plan to use the sailboat for. Sialing the Bahamas or Sailing Caribbean islands or, sailing across the ocean. We've seen too many sailing couples adventure off on...
Lost at Sea Sailing Couple From YouTube Dies in Life Raft – Ep 308 – Lady K Sailing
Lady K Sailing

Lost at Sea Sailing Couple From YouTube Dies in Life Raft – Ep 308 – Lady K Sailing

A sailing couple with a great YouTube channel sails off on an Atlantic Crossing to Portugal on their 42 foot Gib’sea ketch cruising sailboat and is lost at sea. A rescue begins and the boat is never found until they wash ashore on Sable Island in a life ...
Home AWAY From Home | SailAway 296
SailAway World Sailing

Home AWAY From Home | SailAway 296

It's been SO LONG since we both visited friends and family in the U.S. FINALLY, we're flying back for a full MONTH to catch up, decompress, and enjoy a little holiday cheer. But leaving the boat behind is stressful stuff...and so is a 17-hour travel day!...
Sailing Couple Tragic Accident At Sea – Lady K Sailing Ep 306
Lady K Sailing

Sailing Couple Tragic Accident At Sea – Lady K Sailing Ep 306

A sailing couple wants to live the dream and sail around the world on their CNB 66 foot sailing but sailing from the Caribbean islands to Bermuda and on the Nova Scotia turns deadly when a squall hits their boat and things get out of control sailing in the...
CHEAPEST Options for Young People – Ep 305 – Lady K Sailing
Lady K Sailing

CHEAPEST Options for Young People – Ep 305 – Lady K Sailing

Rent is a huge price now and the cheapest option for tiny living is usually a sprinter van or building a skoolie out of an old school bus but, living on a boat might be even better! Cheap sailboats make great homes and often are cheaper on insurance and mo...
Better To BE DRAGGED Than To DRAG | SailAway 295
SailAway World Sailing

Better To BE DRAGGED Than To DRAG | SailAway 295

PROBLEMS = DRASTIC PLAN CHANGES. We were ALL SET (sorta) to SAIL TO ST. MARTIN to catch our flight BACK TO THE U.S., but our engine had different ideas. So we scramble for a NEW PLAN. Such is life aboard. Enjoy! And be sure to SUBSCRIBE for WEEKLY CON...
SAILING ROUTE – GRENADA – GRENADINES – BEQUIA and our ANCHOR WASHDOWN BOAT HACK!
Sailing PILAR - Blue Dot Voyages

SAILING ROUTE – GRENADA – GRENADINES – BEQUIA and our ANCHOR WASHDOWN BOAT HACK!

Time to sail north from Grenada to Bequia. - the first leg of our journey home to SC. Getting real hot here - only 10 degrees from the equator. It’s only about 40 miles, so even though we left mid morning, we should be in Bequia before dark. TIMELINE:...
MASSIVE STORM hits Sailboat Race in Mobile Alabama – Ep 304 – Lady K Sailing
Lady K Sailing

MASSIVE STORM hits Sailboat Race in Mobile Alabama – Ep 304 – Lady K Sailing

The sailboat races to Dauphin Island Alabama was hit my a massive storm system that started in Texas and collided with a 125 entry sailboat race. In all, 40 people were rescued in this horrible sailing disaster, 8 boats lost to the sea and 6 casualties rep...
Bayesian Disaster VS New York Times – Unsinkable! Ep 303 – Lady K Sailing
Lady K Sailing

Bayesian Disaster VS New York Times – Unsinkable! Ep 303 – Lady K Sailing

Perini Navi, owners of the company who built the Bayesian Superyacht that sank in Italy in a sudden weather event are filing suit against the New York Times claiming the Bayesian was unsinkable, blaming the crew for mistakes made when the sailboat superyac...
ANOTHER Motor DOWN? | SailAway 294
SailAway World Sailing

ANOTHER Motor DOWN? | SailAway 294

The perfect time for a CRITICAL ISSUE with our ONE RUNNING MOTOR. We're just trying to LEAVE GRENADA. We have a plane to catch to the US in less than TWO WEEKS in ST. MARTIN. We have drastic plans to get TWO GOOD MOTORS back in this boat. We just have...
Junk Sailboat, or Great Cheap Boat? – Ep 302 – Lady K Sailing
Lady K Sailing

Junk Sailboat, or Great Cheap Boat? – Ep 302 – Lady K Sailing

Are you sailboat shopping? Here are some great tips to buying your firsat sailboat including how to inspect it, insure it, and own it. WHat to look for in a sailboat and what to avoid. Some sailboats are just junk and some have a lot of life left to help y...
The Moorings and Sunsail Charter Boats – Is it Worth It? Ep 301 – Lady K Sailing
Lady K Sailing

The Moorings and Sunsail Charter Boats – Is it Worth It? Ep 301 – Lady K Sailing

The Moorings and Sunsail and other charter boat companies have owners buy the boats for them, use them in the charter industry for five years, and then the owner can keep the boat. Does this financially make sense for you? Here's how charter to ownership w...
WELCOME to the JUNGLE! – Our Favorite Grenada Pastime | SailAway 293
SailAway World Sailing

WELCOME to the JUNGLE! – Our Favorite Grenada Pastime | SailAway 293

HASH TIME! In ALL the islands we've traveled, this is OUR FAVORITE LOCAL PASTIME. It's not our first. We've done MANY in years past and EVERY SINGLE ONE is different. Come see what the HASH HOUSE HARRIERS is all about. Enjoy!! And be sure to SUBSCRIBE...
A Scooter with GUSTO – iEnyrid M4PRO S+ | SailAway Review
SailAway World Sailing

A Scooter with GUSTO – iEnyrid M4PRO S+ | SailAway Review

This GO ANYWHERE scooter has serious power and speed for a GREAT price. But like all of these things, there are some quirks. Check out ALL the pros and cons. HERE! Enjoy!! And be sure to SUBSCRIBE for WEEKLY CONTENT EVERY SUNDAY! Cheers!! Thanks for ...
BAD Sailboats – What NOT to Buy – Ep 300 – Lady K Sailing
Lady K Sailing

BAD Sailboats – What NOT to Buy – Ep 300 – Lady K Sailing

Charlie the Truck is here! youtube.com/@UCxNBI1BNvOgfav6G4utfDWQ This week we look at BAD sailboats and what not to buy, how to spot problems with a sailboat before you go see it, red flags in sailboat for sale ads and boat brokers, damaged sailboats, an...
SURVIVING the HEAT in Prickly Bay | SailAway 292
SailAway World Sailing

SURVIVING the HEAT in Prickly Bay | SailAway 292

The HOTTEST MONTH we've ever experienced in GRENADA. But we've found relief in PRICKLY BAY because here we have so many OPTIONS, not just to cool down, but to make everyday life so much better. Let us SHOW YOU AROUND! Enjoy!! And be sure to SUBSCRIBE f...
Cheap Sailboat to Live On? 38 Foot Sailboat for $30,000 – Ep 299 – Lady K Sailing
Lady K Sailing

Cheap Sailboat to Live On? 38 Foot Sailboat for $30,000 – Ep 299 – Lady K Sailing

Interested in living on or buying a cheap sailboat? Today we look at sailboats for sale right now and compare different sailboat options for live aboard cruising. Want to help support Lady K Sailing? Click here to become a Patron: http://www.patreon.com/l...
ASIWO U1 SUP E-WaterScooter | SailAway REVIEWS
SailAway World Sailing

ASIWO U1 SUP E-WaterScooter | SailAway REVIEWS

A WATERSCOOTER that also doubles as a SUP MOTOR?! This is a cool TWO in ONE package you need to see to appreciate. We'll give you the UPS and the DOWNS of the innovative new WATER SPORTS PRODUCT. Enjoy!! And be sure to SUBSCRIBE for WEEKLY CONTENT EVER...
Sailboats Are Getting Fatter – Why it’s BAD – Ep 298 -Lady K Sailing
Lady K Sailing

Sailboats Are Getting Fatter – Why it’s BAD – Ep 298 -Lady K Sailing

We're almost at 100,000 subscribers! Thank you SO VERY MUCH! This week we talk about boats like the Beneteau Oceanis 40.1 and other brand new designs getting wider and wider in the beam and what that does to their sailing characteristics. How they start to...
When The GROCERIES Get Tough, The Tough Get NACHOS | SailAway 291
SailAway World Sailing

When The GROCERIES Get Tough, The Tough Get NACHOS | SailAway 291

HURRICANE SEASON on a SAILBOAT is a tricky thing, even AFTER you've reached the relative safety of GRENADA. Especially after four previous seasons here, even a couple months in the same spot feels like a LONG time. But we've figured out a few tricks to m...
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