Watch Sailing & Boating Adventures Around the World tagged “Caribbean” – Page 6 of 157

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Engine Fails at Sea + Spinnaker Disaster! | 60 Mile Sail Gone Wrong
Sailing Doodles

Engine Fails at Sea + Spinnaker Disaster! | 60 Mile Sail Gone Wrong

We set off on what was supposed to be a beautiful 60-mile open ocean sail aboard our classic sailing yacht—but things quickly took a turn. Out in the middle of the sea, our engine failed to start, and to make matters worse, the spinnaker got jammed and w...
Why Do I Feel so NERVOUS This Time? – The Lazy Geckos Ep. 323
Lazy Gecko Sailing & Adventures

Why Do I Feel so NERVOUS This Time? – The Lazy Geckos Ep. 323

The journey starts in Palm Harbor, where docking is tricky due to currents. Concerns about the generator lead to buying a backup. Preparations include weather checks and safety measures. Family dynamics unfold, resulting in minor accidents. A safety briefi...
Cat Island in the Bahamas has beautiful water and beaches
Sailing Doodles

Cat Island in the Bahamas has beautiful water and beaches

Set sail with us to Cat Island in the Bahamas, where our classic yacht drops anchor off stunning turquoise waters. Join our two mini labradoodles as we hike to the highest point in the country—Mount Alvernia—home to a tiny stone monastery built by a he...
SIMPLE JOB, BIG REWARD: how the engine gives us hot showers on our sailboat! DIY
Sailing Jibsea

SIMPLE JOB, BIG REWARD: how the engine gives us hot showers on our sailboat! DIY

Travis gets our Yanmar 4JH2E engine to tie in with our hot water heater. A simple DIY that has provided us with hot showers! NEW VIDEOS EVERY SUNDAY! Please subscribe and share our videos - every bit of support is much appreciated, keeps our journey going...
Ep. 66 A bug in the system?
SAILING into FREEDOM

Ep. 66 A bug in the system?

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 ...
700,000 Subscribers!  Wow!
Sailing Doodles

700,000 Subscribers! Wow!

Celebrating 700,000 subscribers on Youtube! Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ This channel is funded by v...
SSL734 ~ Captain’s Update
Captain Rick Moore

SSL734 ~ Captain’s Update

Happy Sunday Everyone! Today we send you an update of our travels the past little while that we've been missing in action.. sorry for the quiet lately but we've been enjoying some family time and traveling with new friends with families on boats also.. al...
Stranded at Cat Island! Engine Troubles Before a Perfect Sail to Paradise
Sailing Doodles

Stranded at Cat Island! Engine Troubles Before a Perfect Sail to Paradise

This morning started a little rough... Our engine wouldn’t start as we prepared to leave Cat Island in the Bahamas! ⛵⚙️ After an hour of troubleshooting and some hands-on engine work, I finally got it running. We then set sail for New Bight, a gorg...
I’m buying a NEW Catamaran! But which one?
Sailing Doodles

I’m buying a NEW Catamaran! But which one?

After 9 unforgettable years sailing across the world, I'm thrilled to announce my next big adventure — I'm getting a brand new Catamaran! In this video, I’ll take you through a journey of the incredible memories we've made together and reveal what’s...
Join me in the galley!👩🏻‍🍳⛵️#galley #boats #sailboats #cooking
Sailing Jibsea
We Set Sail in Perfect Conditions… Until I Made a Big Mistake | Sailing to Cat Island
Sailing Doodles

We Set Sail in Perfect Conditions… Until I Made a Big Mistake | Sailing to Cat Island

We finally cast off the dock and head out into perfect sailing conditions — the kind you dream about! Spirits are high as we hoist the sails, but things take a turn when I make a critical mistake that damages the boat. With some quick thinking (and a lit...
Work Hard, Party Hard: Content Creation on the Water – The Lazy Geckos Ep, 322
Lazy Gecko Sailing & Adventures

Work Hard, Party Hard: Content Creation on the Water – The Lazy Geckos Ep, 322

We're out on the water, waiting for what seems to be forever! Come see how we fill the time with content creation, chores and more! If you enjoy our videos, please SUBSCRIBE! Check out our webpage at www.lazygeckos.net Other Links: Server: Visit our p...
This Marina has a hidden DANGER…. SHARKS!!!!
Sailing Doodles

This Marina has a hidden DANGER…. SHARKS!!!!

We sail our classic yacht to Cape Eleuthera where we get a marina for the first time in more than a month. But this Marina has a dangerous secret... It is patrolled by lots of BULL SHARKS that make falling in the water very dangerous! This channel is fu...
Ep. 65 Nav station, saloon design and sails
SAILING into FREEDOM

Ep. 65 Nav station, saloon design and sails

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 ...
Sailing Off-Grid in One of the World’s Last Untouched Paradises | Sailing Sitka Ep 164
Sailing Sitka

Sailing Off-Grid in One of the World’s Last Untouched Paradises | Sailing Sitka Ep 164

In this episode, Jay and Kenna welcome aboard their friends from Canada and give them the full tropical, sailing experience by island hopping and cruising through the San Blas islands. We are sailing off-grid between sand spit islands in search for adventu...
She might hate me after this!
Sailing Doodles

She might hate me after this!

We kick things off with some epic wing foiling sessions in the crystal-clear waters of Governor's Harbour, Bahamas! Then it's time to weigh anchor and head south to Rock Sound, where we do a little land exploring—and stumble upon a cave full of bats! Thi...
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...
New Crew Drama & Dangerous Sailing Through a Treacherous Cut!
Sailing Doodles
Ep. 64 Sailing into Freedom goes INTERNATIONAL !
SAILING into FREEDOM

Ep. 64 Sailing into Freedom goes INTERNATIONAL !

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 ...
Blue Holes, Caves, Bikinis & Big Waves at the Queen’s Bath!
Sailing Doodles

Blue Holes, Caves, Bikinis & Big Waves at the Queen’s Bath!

In this episode of Sailing Doodles, we explore the stunning island of Eleuthera in the Bahamas! We hike through ancient caves, brave the massive waves crashing at the Queen’s Bath, and visit the iconic Glass Window Bridge. The adventure heats up when the...
Stir-Crazy Crew! Trapped on a Boat for DAYS! –  The Lazy Geckos Ep. 321
Lazy Gecko Sailing & Adventures

Stir-Crazy Crew! Trapped on a Boat for DAYS! – The Lazy Geckos Ep. 321

The crew has been stuck aboard for days while waiting on a weather window in order to cross the Gulf Stream to the Bahamas! We're going a little crazy over here, come see how we fill the time! If you enjoy our videos, please SUBSCRIBE! Check out our webp...
Getting my crew to help me sail our classic yacht!
Sailing Doodles

Getting my crew to help me sail our classic yacht!

We pull anchor in beautiful Harbour Island and set our course through the infamous Devil’s Backbone—a tricky and narrow passage known for testing even seasoned sailors. Things get rough along the way, but with some teamwork and steady hands, we make it...
Cleaning the Boat, Caribbean Style – In the Rain! ⛵️🏝️  #sailing #boatlife #paradise
PAT | FRANKIE

Cleaning the Boat, Caribbean Style – In the Rain! ⛵️🏝️ #sailing #boatlife #paradise

When life gives you rain, dance in it! ☔️ While anchored in paradise, Frankie turned a rainy day into a bikini boat-cleaning dance party. #makethebestofit Our computer is not ready yet, but we have to share this short 😂
MEASURE 3 TIMES, CUT ONCE! – Tackling what most wouldn’t dare🫣 – Ep 231
Sailing Jibsea

MEASURE 3 TIMES, CUT ONCE! – Tackling what most wouldn’t dare🫣 – Ep 231

We take on one of the most intimidating DIY boat projects, shortening the boom of our aluminum sailboat while docked in the stunning French and Dutch island if St Martin/Sint Maarten in the eastern Caribbean. It’s the kind of job most cruisers wouldn’t...
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