Watch Sailing & Boating Adventures Around the World tagged “Sailing caribbean” – Page 2 of 35

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Showing 25-48 of 832 results
3 STEPS, So easy you can SKIP ONE! Ep 340 – Lady K Sailing
Lady K Sailing

3 STEPS, So easy you can SKIP ONE! Ep 340 – Lady K Sailing

Learnign to sail in three easy steps that are so beginner and simple you can actually skip one and learn to sail a small sailboat in two simple steps. Learning how to sail doesn't have to be difficult. Let me know in the comments if this video helped you l...
EASY YouTube HOW TO MAKE SAILING VIDEOS – Ep 339 – Lady K Sailing
Lady K Sailing

EASY YouTube HOW TO MAKE SAILING VIDEOS – Ep 339 – Lady K Sailing

Last week we talked about making YouTube videos for sailing and a lot of you were interested in the DIY process of actually making a video from start to finish, how to make money and edit videos. So today, we take a tour of the life of a sailing youtube. T...
What it takes to keep this dream alive | Sailing Sitka Ep 177
Sailing Sitka

What it takes to keep this dream alive | Sailing Sitka Ep 177

Jay and Kenna have arrived at a new destination—Green Island, a stunning atoll tucked within the San Blas Islands. While this lifestyle often feels like a dream and looks like something straight off a postcard, it takes real balance to maintain it. Could...
Our boat nearly quit, but we didn’t! | Sailing Sitka Ep 176
Sailing Sitka

Our boat nearly quit, but we didn’t! | Sailing Sitka Ep 176

Jay and Kenna set sail from the sheltered anchorage of Chicheme, continuing their journey through the San Blas Islands to a remote and desolate new spot—though, unsurprisingly, not without a few hiccups along the way.
HOW TO CHECK SAILING WEATHER – Ep 337 – Lady K Sailing
Lady K Sailing

HOW TO CHECK SAILING WEATHER – Ep 337 – Lady K Sailing

Sailing safely is key and having a sail plan is critical to a good sailing day. I use Windfinder to see the wind and waves and plan my sailing trip to make sure I know what to expect, have a back up plan, and bail out points. Choosing how much wind is too...
FIVE CRITICAL Lessons to Learn BEFORE you Set Sail – Ep 336 – Lady K Sailing
Lady K Sailing

FIVE CRITICAL Lessons to Learn BEFORE you Set Sail – Ep 336 – Lady K Sailing

Dream of sailing off into the sunset? Living on a sailboat can be an exciting life but also hard. Here are five lessons I've learned along the way to help you be successful in quiting land life and living on a sailboat. Want to help support Lady K Sailing...
Lacros Pinecone Fat Tire E-Bike | SailAway Reviews
SailAway World Sailing

Lacros Pinecone Fat Tire E-Bike | SailAway Reviews

The good folks at Lacros sent us this fabulous e-bike a while back for review, and though it took us a while to get to it, the wait was worth it. Enjoy!! And be sure to SUBSCRIBE for WEEKLY CONTENT EVERY SUNDAY! Cheers!! Thanks for watching SailAway, th...
We’re BACK! And BOAT Keeps Getting BETTER | SailAway 312
SailAway World Sailing

We’re BACK! And BOAT Keeps Getting BETTER | SailAway 312

TEAK? Noooo. FAUX TEAK. Noooo. PE EVA FOAM?? Hell yes! This week we're finally upgrading our decking with TopDeck PE EVA Flooring. This is the good stuff...unlike the cheap stuff we tried just for kicks. We'll show you how it goes down and why it's becomin...
Gemini 105MC Review: The Affordable Cruising Catamaran That Actually Delivers! Ep 335 Lady K Sailing
Lady K Sailing

Gemini 105MC Review: The Affordable Cruising Catamaran That Actually Delivers! Ep 335 Lady K Sailing

Looking for a smart, budget-friendly catamaran that’s actually comfortable, capable, and fun to sail? Meet the Gemini 105MC—one of the most popular American-built catamarans ever made! In this video, we dive deep into what makes this 34-foot catamaran ...
BAGGYWRINKLE? NEED to KNOW Sailing Words – Ep 334 – Lady K Sailing
Lady K Sailing

BAGGYWRINKLE? NEED to KNOW Sailing Words – Ep 334 – Lady K Sailing

Learing how to sail can be hard, but learning the ridiculous vocabulary makes sailing scary! Today we cover some of the need to know words you need to learn if you're going to be learning how to sail. Learn how to use the TELL TALES to TRIM a sail, which s...
The INSANE PRICE of a Beneteau Sense 50! – Ep 333 – Lady K Sailing
Lady K Sailing

The INSANE PRICE of a Beneteau Sense 50! – Ep 333 – Lady K Sailing

Why Is the Beneteau Sense 50 So Expensive? Used Sailboat Prices Explained In this video, we dive into the world of the Beneteau Sense 50, a luxury cruising sailboat that still commands a steep price tag—even when it's over a decade old. What makes this ...
Learn to SAIL for FREE! Or Find Good Crew Here! Ep 332 – Lady K Sailing
Lady K Sailing

Learn to SAIL for FREE! Or Find Good Crew Here! Ep 332 – Lady K Sailing

Are you interested in learning how to sail for free? Or looking for crew for your sailboat for free? Join us on crewfinder for the east coast or the Great Lakes so learn to sail, teach people how to sail, or get help sailing your sailboat! East coast crew...
TOP 3 Small Sailboats You Can Sail AROUND THE WORLD! Ep 331 – Lady K sailing
Lady K Sailing

TOP 3 Small Sailboats You Can Sail AROUND THE WORLD! Ep 331 – Lady K sailing

This week we look at the top three small sailboats you can sail around the world. 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 roller furling to sailboat toilets to sailboat en...
HOCKEY in GRENADA & BEER in a SHOE | SailAway 311
SailAway World Sailing

HOCKEY in GRENADA & BEER in a SHOE | SailAway 311

GRENADA is FULL of SURPRISES! Even when we've LIVED HERE on and off for nearly 6 YEARS. This is a very SAILBOAT LIFE video, but we pack in a lot of unexpected tasks and past times. Enjoy!! And be sure to SUBSCRIBE for WEEKLY CONTENT EVERY SUNDAY! Cheers...
Sabre 38’s Cored Hull – Excellent sailboat, or one to stay away from? – Lady K Sailing – ep 330
Lady K Sailing

Sabre 38’s Cored Hull – Excellent sailboat, or one to stay away from? – Lady K Sailing – ep 330

Join us for an in-depth look at the Sabre 38 sailboat, a timeless cruiser-racer known for its quality craftsmanship, solid performance, and enduring appeal. In this video, we take you on a full tour above and below deck, explore its sailing characteristics...
No More Anchoring in Florida?! – Ep 329 – Lady K Sailing
Lady K Sailing

No More Anchoring in Florida?! – Ep 329 – Lady K Sailing

Are you sailing to the Bahamas? New laws in progress in Florida may make it much harder to sail the east coast and on the the Caribbean! Anchoring in Flroida is a pivotal part of the boat life cruising experience on the east coast and these laws could chan...
Exorcising DEMONS | SailAway 310
SailAway World Sailing

Exorcising DEMONS | SailAway 310

It's SPLASH TIME! Which means HIGH ANXIETY. With a NEW ENGINE and TWO MONTHS of boat yard work behind us, we're crossing fingers and toes that nothing goes wrong when dropped in the water and placed into service. And then it's the FIRST PASSAGE since a ste...
Sailing Mexico to California: Couple Disappears on Sailboat – Ep 328 – Lady K Sailing
Lady K Sailing

Sailing Mexico to California: Couple Disappears on Sailboat – Ep 328 – Lady K Sailing

John's channel, Far Reach Voyages is here: @FarReachVoyages John's video for Miliatry vets is here: www.youtube.com/watch?v=fBGEhZWm1I4&t Searchers on Monday and Tuesday said they found no sign of the sailing vessel Ocean Bound, which was sailing fr...
Sailing to the Bahamas on a Budget – Ep 327 – Lady K Sailing
Lady K Sailing

Sailing to the Bahamas on a Budget – Ep 327 – Lady K Sailing

The beauty of the Bahamas is explored on a cheap sailboat. How to sail to the Bahamas and which boat to use. How to outfit a sailboat to liveaboard and sail it to the Bahamas from Florida or the Great Lakes to the ocean. I had this dream to quit work and b...
It’s ALIVE It’s ALIVE!! | SailAway 309
SailAway World Sailing

It’s ALIVE It’s ALIVE!! | SailAway 309

Well, MOSTLY. There were SO MANY STEPS leading up to actually installing our NEW ENGINE. But there's still SO much to do to make it ACTUALLY RUN. Not to mention the REST of our long list of jobs to complete, including BOTTOM PAINT. And the clock is ticking...
EASY 40 Foot Sailboats Selling CHEAP – Ep 326 –  Lady K Sailing
Lady K Sailing

EASY 40 Foot Sailboats Selling CHEAP – Ep 326 – Lady K Sailing

Are you looking for a 40 foot sailboat to live aboard? A great couples sailboat or single handed sailboat? This week, we look at cheap and easy to live with 40 footers like Beneteau and Jeanneau and answer questions about sailboats ont he hunt for the best...
Like a VERY TIGHT GLOVE | SailAway 308
SailAway World Sailing

Like a VERY TIGHT GLOVE | SailAway 308

For nearly 3000 MILES we sailed Ophelia WITHOUT a PORT ENGINE. Today, we're finally remedying that issue. We just have to cram a BIG ENGINE through a SMALL HATCH to get it done. Enjoy!! And be sure to SUBSCRIBE for WEEKLY CONTENT EVERY SUNDAY! Cheers!! ...
RACING AGAINST THE CLOCK: How we nearly missed our chance to sail away – Ep 233
Sailing Jibsea

RACING AGAINST THE CLOCK: How we nearly missed our chance to sail away – Ep 233

Go to https://surfshark.com/jibsea or use code JIBSEA at checkout to get 4 extra months of Surfshark VPN! Join us as we finally leave Sint Maarten and set off on an 80 nautical mile night sail to the British Virgin Islands! After days of prepping, provis...
BEST Bluewater Are NOT What You Think! Ep 325 – Lady K Sailing
Lady K Sailing
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