Watch Sailing & Boating Adventures Around the World tagged “Sailing caribbean” – Page 8 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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A SUNKEN Wreck 15 FEET UNDER our SAILBOAT| SailAway 261
SailAway World Sailing

A SUNKEN Wreck 15 FEET UNDER our SAILBOAT| SailAway 261

ANCHORING is often an ADVENTURE. But discovering a SUNKEN SAILBOAT DIRECTLY BENEATH YOU that is UNCHARTED is a new one for us! We also show you a big slice of HOLIDAY ISLAND LIFE as we celebrate CHRISTMAS in the ISLANDS and ring in an EXCITING NEW YEAR. ...
Big Beneteau’s Big Problem – Ep 263 – Lady K Sailing
Lady K Sailing

Big Beneteau’s Big Problem – Ep 263 – Lady K Sailing

There are two sailboats boats that people buy A LOT of. They’re for more than just lake sailing though. Being near 40 feet they’re a little much for mom and pop marinas and yacht clubs. They’re weekenders. Coastal cruisers. And if you want them to be...
ENDING a CHAPTER – Catamaran Life | SailAway 260
SailAway World Sailing

ENDING a CHAPTER – Catamaran Life | SailAway 260

We're BACK in the VIRGIN ISLANDS where BIG CHANGES AWAIT us. But those changes are only an ENDS TO A MEANS with an ATLANTIC CROSSING in our sites. We show you some of our favorite sights as we gear up to GET TO WORK. Enjoy!! And be sure to SUBSCRIBE for...
BIG NEWS! Sailing Youtuber Meets Practical Sailor! – Ep 262 – Lady K Sailing
Lady K Sailing

BIG NEWS! Sailing Youtuber Meets Practical Sailor! – Ep 262 – Lady K Sailing

This week, Practical Sailor called me!!! A lowly sailing youtuber that refuses to use sailing bikini girls to get views gets a call from Practical Sailor Magazine. #sailing #bikini #sailingmagazine #sailboatreviews #boattours #sailingbahamas #sailboat Ne...
Getting READY for a CHANGE | SailAway 259
SailAway World Sailing

Getting READY for a CHANGE | SailAway 259

A NEW CHAPTER is about to begin for SAILAWAY. As we enjoy a few favorite St. Martin spots, we have to GET MOVING toward ST. THOMAS and some BIG CHANGES in our lives. But if there's one thing we've learned in this life, it's how to roll with it...change i...
Unveiling the Hunter Legend Sailboat: A Comprehensive Review, Sailing Adventure Ep261 Lady K Sailing
Lady K Sailing

Unveiling the Hunter Legend Sailboat: A Comprehensive Review, Sailing Adventure Ep261 Lady K Sailing

🌊 Set sail on a nautical journey with our latest video as we explore the captivating world of the Hunter Legend Sailboat! 🚤⚓ Are you passionate about sailing or considering a new addition to your maritime adventures? Look no further! In this in-de...
Buying a Boat in Caribbean Grenada – Taxes, Surveys, Customs! Ep 260 – Lady K Sailing
Lady K Sailing

Buying a Boat in Caribbean Grenada – Taxes, Surveys, Customs! Ep 260 – Lady K Sailing

This week we take a look at how hard it is to buy a sailboat in a Caribbean country like Grenada. Getting a broker, going to see the boat, getting a survey, and dealing with all the hurdles of keeping a boat in Grenada. Customs, Immigration, and taxes! Oh ...
New Cat SINKING, Old Cat SAILING | SailAway 258
SailAway World Sailing

New Cat SINKING, Old Cat SAILING | SailAway 258

ONCE AGAIN we find ourselves next to a SINKING CATAMARAN. As the FIGHT to SAVE THE BOAT we can't help but wonder COULD OUR CATAMARAN SINK? Considering boat is 30 YEARS OLDER than the sinking boat our conclusions are a little unexpected. We also have an ...
On The SET of a TV SHOW! – Life On A 48′ CATAMARAN | SailAway 257
SailAway World Sailing

On The SET of a TV SHOW! – Life On A 48′ CATAMARAN | SailAway 257

We've found the CROWN JEWEL of GUADELOUPE - Deshaies. Not only is this a GREAT PLACE to get STUCK, but it's also the SET of an INCREDIBLY POPULAR TV SHOW! We show you all the sites, both OFF THE BEATEN PATH and touristy as well. Enjoy!! And be sure to ...
Three Things That’ll Make You HATE Living On A Boat  – EP 259 – Lady K Sailing
Lady K Sailing

Three Things That’ll Make You HATE Living On A Boat – EP 259 – Lady K Sailing

This week we talk about needing writers for sailing articles and explore things that you can plan for and solve ahead of time before you move on a sailboat or buy a sailboat to live aboard. We talk about water makers, solar panels, electricty, and sailboat...
SAILING FAST and BREAKING STUFF | SailAway 256
SailAway World Sailing

SAILING FAST and BREAKING STUFF | SailAway 256

Our TIME is SHORT, so only PERFECT ANCHORAGES will do. We take an UNTESTED ROUTE north to GUADELOUPE for the FIRST TIME, narrowly skirting east of DOMINICA. It's a LOT OF SAILING in some STRONG and UNPREDICTABLE conditions resulting in some HARDWARE FAIL...
How Cheap is TOO Cheap? Sailboat Problems – Ep 258 – Lady K Sailing
Lady K Sailing

How Cheap is TOO Cheap? Sailboat Problems – Ep 258 – Lady K Sailing

#cheapboat #sailboat #sailing #boatshop How cheap of a sailboat is too cheap? Can you replace an engine? Recore a deck? When do we walk away of cut a sailboat up? Buying a sailboat can be hard, but it doesn't have to be! Things to look for buying a boat, ...
Top 5 Small Sailboats You Can Live On! Ep 257 – Lady K Sailing
Lady K Sailing

Top 5 Small Sailboats You Can Live On! Ep 257 – Lady K Sailing

#tinyhouse #tinyliving #offthegridliving #sailing #sailboat This week we look at the top five small sailboats you can live on. What makes a good off the grid liveaboard sailboat? What do you NEED to have on a sailboat to live on, sail alone solo, from rol...
Anchor Chain FOULED 100m from SHORE | SailAway 255
SailAway World Sailing

Anchor Chain FOULED 100m from SHORE | SailAway 255

A BOULDER on the ocean floor WRAPS our CHAIN in a CRAZY KNOT. We're only 100m from shore with GUSTING and VARIABLE WIND and CURRENTS. Time for Eric to GO DIVING! We also happen to be at the foot of a MASSIVE VOLCANO in the captivating town of Sainte Pie...
We LEFT THE RAT RACE for a LIFE AT SEA! – Classic Catamaran Restoration | SailAway 254
SailAway World Sailing

We LEFT THE RAT RACE for a LIFE AT SEA! – Classic Catamaran Restoration | SailAway 254

We GAVE UP EVERYTHING to SAIL THE WORLD FULL TIME. Then we traded our MONOHULL for a 30 year old CATAMARAN. We've sailed several passes of the WEST INDIES, PUERTO RICO, and the BAHAMAS, including a round trip of over 3500 miles from GRENADA to the US and...
Make a $#!T Load of Money from a Boat! And Boat Vocabulary Explained – Ep 256 – Lady K Sailing
Lady K Sailing

Make a $#!T Load of Money from a Boat! And Boat Vocabulary Explained – Ep 256 – Lady K Sailing

How to make money working from a boat while sailing is a BIG question - and no, we don't mean a YouTube channel. There are ways to make money living on a boat, work remotely from anywhere in the world, and companies that will hire you knowing full well you...
Big Heavy Sailboats Are Bad – Ep 255 – Lady K Sailing
Lady K Sailing

Big Heavy Sailboats Are Bad – Ep 255 – Lady K Sailing

This week we discuss big heavy sailboats for sailing the Bahamas and Caribbean, living on a sailboat, and why while they hold their value and can sail oceans and big waves, they might not be the right choice to retire on a sailboat or sail from Bimini Bah...
PIRATE ANXIETY – Mystery Boat AT SEA | SailAway 253
SailAway World Sailing

PIRATE ANXIETY – Mystery Boat AT SEA | SailAway 253

CONCERN about PIRACY on an OPEN OCEAN PASSAGE is unavoidable, even though we all know it's uncommon. We've been seemingly closely followed several times while at sea. When a non-descript power vessel follows your track for hours with no land in sight, how...
A RADICAL Solution For Our DEAD MOTOR | SailAway 252
SailAway World Sailing

A RADICAL Solution For Our DEAD MOTOR | SailAway 252

7 MONTHS and we STILL haven't FIXED OUR MOTOR. That's because we're considering an UNUSUAL SOLUTION. It'll be a lot of work, much of it custom, but we think ELECTRIC may be the answer. We'll explain why, PLUS it's finally time for us to set sail again. ...
Worst Sailboats – What Not To Buy – Ep 254 – Lady K Sailing
Lady K Sailing

Worst Sailboats – What Not To Buy – Ep 254 – Lady K Sailing

This week we take a look at a couple of the worst sailboats you can buy if your boat shopping to go cruising or live aboard in the Bahamas or Caribbean. The bad sailboats that are actually being used as live aboard cruisers right now. Sailboat problems, ba...
Giving BACK To GRENADA – LIFE on a CLASSIC CAT | SailAway 251
SailAway World Sailing

Giving BACK To GRENADA – LIFE on a CLASSIC CAT | SailAway 251

A STERN CONCERT for a GREAT CAUSE and...are our GENERATOR ISSUES OVER?? Plus, waterfalls, a chocolate museum, and a fish market...with Chris and Mary arriving, Loren's birthday upon us, and our departure imminent, we're squeezing in as much of the good st...
Are Sailing Youtubers Just Drunk? Ep 253 – Lady K Sailing
Lady K Sailing

Are Sailing Youtubers Just Drunk? Ep 253 – Lady K Sailing

This week we talk about alcohol on boats and how never meeting your heroes might be sage advice when it coems to sailing youtubers. We look at drinking and boating, alcoholism and boating, bahamas rum drinking and sailing, bikini grils in the bahamas, and ...
TOP 5 Essential Boat Shopping Tips – Ep 252 – Lady K Sailing
Lady K Sailing

TOP 5 Essential Boat Shopping Tips – Ep 252 – Lady K Sailing

Historsea episode on the America's Cup: https://www.youtube.com/watch?v=Mgv9YfWOGoI&t Need a consult? Click here to drop a message: https://ladyksailing.com/consults/ Want to help support Lady K Sailing? Click here to become a Patron: http://www.patr...
LEAVING Our CATAMARAN For A TINY HOUSE | SailAway 250
SailAway World Sailing

LEAVING Our CATAMARAN For A TINY HOUSE | SailAway 250

LIVING on a 30-year-old CATAMARAN can be EXHAUSTING. We finally hit a point where we NEEDED a change of pace, somewhere on LAND. And since we're in the LAND of CHOCOLATE here in Grenada, what better spot than a CHOCOLATE PLANTATION?! We spend 3 days (an...
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