Watch Sailing & Boating Adventures Around the World tagged “Caribbean” – Page 3 of 156

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 49-72 of 3730 results
Sailing Solo After Crew Drama – Peaceful Until THIS Happened!
Sailing Doodles
Sailing Solo After Crew Drama – Peaceful Until THIS Happened!
After parting ways with my crew in the last episode, I’m finally sailing solo through the beautiful Abacos. Island hopping alone has its perks—peace, quiet, and full control of the boat. But the freedom comes with a price… boat maintenance doesn’t ...
⛵️Installing our NEW LEWMAR HATCH | Hallberg Rassy 352 Sailboat REFIT
Sailing Joco
⛵️Installing our NEW LEWMAR HATCH | Hallberg Rassy 352 Sailboat REFIT
THAT'S WHAT SHE SAID! comment below if you're reading this ;) In this episode we finally...finally!!! FINALLY !!! install fixtures up on deck and close up all the holes! We also party with another Hallberg Rassy & make some tasty dumplings. But not bef...
Drama with the Crew,  Trouble in Paradise
Sailing Doodles
Drama with the Crew, Trouble in Paradise
We sail into one of the most iconic spots in the Abacos—Tahiti Beach, home to an epic floating bar and grill right on the sandbar. The vibe starts out fun, sunny, and full of tropical cocktails… but things take a turn. After some tension on board, I e...
Back on a Catamaran… and I Might Not Give It Back!
Sailing Doodles
Back on a Catamaran… and I Might Not Give It Back!
Join us as we hop aboard my friend’s Leopard 48 sailing catamaran and sail through the stunning Abacos! We anchor at one of the best snorkeling spots in the Bahamas, where the crystal-clear water is full of vibrant marine life. After reeling in a fresh m...
We Caught Tuna in the Bahamas and Sailed to Paradise!
Sailing Doodles
We Caught Tuna in the Bahamas and Sailed to Paradise!
Things are heating up on the high seas! I’m joined by 4 gorgeous bikini-clad ladies as we go deep-sea fishing—and reel in a massive tuna! The girls did all the work and looked amazing doing it. After the big catch, we set sail from Eleuthera to the stu...
⛵️I FEEL THE BURN🔥 | from BARE to BRUSHED | Hallberg Rassy 352 Sailboat Refit
Sailing Joco
⛵️I FEEL THE BURN🔥 | from BARE to BRUSHED | Hallberg Rassy 352 Sailboat Refit
We can FEEL THE BURN! Guys, it's HOT. Like - Real Hot. We keep pushin on to get these last projects done so we can leave the boatyard and in this episode we finish fiberglassing the starboard deck & ... wait for it ... PUT PAINT DOWN! It's extremely exciti...
Challenges We Face While Living Remotely on a Boat – The Lazy Geckos Ep. 328
Lazy Gecko Sailing & Adventures
Challenges We Face While Living Remotely on a Boat – The Lazy Geckos Ep. 328
We're in the islands baby! Which offer beautiful beaches and relaxation, but it also comes with challenges like a broken water maker and generator. We'll have discussions about repairs and our frustrations, while cooking plans showcase food choices and mea...
Meet My 3 New Bikini Crew! Let the Adventure Begin 🌊👙
Sailing Doodles
Meet My 3 New Bikini Crew! Let the Adventure Begin 🌊👙
Big changes aboard! In this episode, we kick things off with some deep sea fishing action and land a nice mackerel before diving into the crystal-clear waters for some epic scuba. But the real headline? I welcome three stunning new crew members to join me ...
They Just Got Here… and Now They’re Leaving?!
Sailing Doodles
They Just Got Here… and Now They’re Leaving?!
New crew joined the boat—but just as quickly as they arrived, they had to leave. I dropped them off at the ferry dock in Harbour Island so they could catch a flight home. After that, I hopped on a center console and went fishing around the beautiful wate...
Ep. 70 4.5kW of solar panels – ElCano World Challenge here we come!
SAILING into FREEDOM
Ep. 70 4.5kW of solar panels – ElCano World Challenge here we come!
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 To A HIDDEN Beach And Letting Loose With Nature.
SailorBarry
Horseback Riding on a Dream Beach in the Bahamas!
Sailing Doodles
Horseback Riding on a Dream Beach in the Bahamas!
We set sail from Spanish Wells to the stunning Harbour Island, home of the world-famous Pink Sands Beach! 🐢 Along the way, we discover a magical bay where dozens of sea turtles swim right up to us—and even eat out of our hands! Then we welcome back re...
What REALLY Happens When You’re STUCK at Anchor – The Lazy Geckos Ep. 327
Lazy Gecko Sailing & Adventures
What REALLY Happens When You’re STUCK at Anchor – The Lazy Geckos Ep. 327
The crew express excitement about being in the islands but face frustration due to weather delays affecting their plans. Safety lessons and techniques are shared, and reflections on their anchorage reveal mixed feelings. All before maintenance issues arise...
SSL735 ~ Burnout is REAL
Captain Rick Moore
SSL735 ~ Burnout is REAL
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...
⛵️YOU WON’T BELIEVE WHAT WE FOUND! Cleaning Our SAILBOAT Water Tank – AGAIN | Hallberg Rassy 352
Sailing Joco
⛵️YOU WON’T BELIEVE WHAT WE FOUND! Cleaning Our SAILBOAT Water Tank – AGAIN | Hallberg Rassy 352
WE'RE TIRED! But, the show must go on and there are plenty of things happening on Joco this week. Including finding & fixing a long time problem with our water tank - You won't believe what we found!!! Thank you for all your support!!! Business/Col...
Sailing Bahamas to USA, crossing the Gulf Stream
Igor Stropnik
Sailing Bahamas to USA, crossing the Gulf Stream
Sailing from Ragged Islands, Bahamas to USA, crossing the Gulf Stream on Leopard 50 Sailing Catamaran. http://www.alivesailing.com/ https://www.instagram.com/skipper_igor/
Can We Survive the Yellow Bank Mine Field?
Sailing Doodles
Can We Survive the Yellow Bank Mine Field?
In this episode of Sailing Doodles, we set sail from Highbourne Cay in the Exumas and journey 60 miles across to the stunning Eleuthera island chain. But between us and paradise lies one of the most dangerous passages in the Bahamas—the Yellow Bank. This...
Ep. 69 A Mock-up of the deck gear for very special crew
SAILING into FREEDOM
Ep. 69 A Mock-up of the deck gear for very special crew
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 ...
⛵️EXPOSED!! What Lies BENEATH 40 YEAR OLD Teak Decks (its different)| Hallberg Rassy 352 Sailboat
Sailing Joco
⛵️EXPOSED!! What Lies BENEATH 40 YEAR OLD Teak Decks (its different)| Hallberg Rassy 352 Sailboat
What Lies Beneath - That's kinda scary! We've completed the port side teak deck removal & remediation of Joco but now it's time to do starboard. And what we find is a biiiit different...... Thank you for all your support!!! Business/Collab Inquiries ...
Exploring a Real Cartel Plane Wreck Underwater!
Sailing Doodles
Exploring a Real Cartel Plane Wreck Underwater!
We sail to the legendary Norman’s Cay—once the hideout of the Medellín Cartel—where a drug smuggler’s plane still lies wrecked in the shallow turquoise water. We snorkel the eerie site, then discover a tiny private island that we have completely t...
Sailing from Caribbean to Bahamas
Igor Stropnik
Sailing from Caribbean to Bahamas
Sailing from Caribbean to Bahamas on Leopard 50 Sailing Catamaran. http://www.alivesailing.com/ https://www.instagram.com/skipper_igor/
HORRIBLE?? These are the realities of cruising on a sailboat. – The Lazy Geckos
Lazy Gecko Sailing & Adventures
HORRIBLE?? These are the realities of cruising on a sailboat. – The Lazy Geckos
A sailing trip brings a mix of emotions, from anxiety during rough passages to the joy of cooking a vegetable and pasta dinner. Bug bites create discomfort, prompting discussions on remedies and their effects on daily life. Family roles come into play, hig...
We Found a Secret River in the Bahamas!
Sailing Doodles
We Found a Secret River in the Bahamas!
We set sail from the stunning Warderick Wells to another gem of the Exumas—Shroud Cay. This place is pure magic. We take the dinghy through a unique tidal river that fills with crystal-clear Bahamian water each day, making it feel like we’re flying thr...
The day has finally come 😢 #endofanera #thischangeseverything #nextchapter #newbeginnings
Sailing Honu Time

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