Watch Sailing & Boating Adventures Around the World

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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10 reasons your next vacation should be a sailing charter!
Sail Stillwater

10 reasons your next vacation should be a sailing charter!

10 reason why we think your next vacation should be a sailing charter. A sailing charter could be the ultimate way to escape the ordinary and experience a truly unforgettable vacation on the water. In this video, we reveal 10 reasons why a sailing charter should be your next vacation—from explorin...
The Trinidad You Should Get to Know!
Travel Sketch

The Trinidad You Should Get to Know!

In our opinion, Trinidad's natural beauty is massively under rated! When it comes to Caribbean jungle and waterfalls, and in fact jungle landscapes in general, it's world class. When our new crew member Lukasz arrived in Trinidad to join us living aboard our sailboat, we knew we wanted to...
Ultimate SAILING Itinerary for Antigua
Sail Stillwater

Ultimate SAILING Itinerary for Antigua

In this video we are chartering a Sunsail 46' monohull out of English Harbor and sailing the beautiful Caribbean islands of Antigua and Barbuda. We'll bring you along as we hit all of the hot spots and show you the best anchorages and things to do on the islands. With stops like Green Is...
We Traded the Ocean for the Mountains | Our Journey to Minca, Colombia
Sailing Big Lost

We Traded the Ocean for the Mountains | Our Journey to Minca, Colombia

We’re a family sailing full-time, exploring the Caribbean and Central America aboard our sailing catamaran Big Lost. New episodes every Tuesday at 10:30 AM ET. In this episode of Sailing Big Lost, we head inland for a change of scenery—trading the Caribbean coast for the lush mountains of Minca, Co...
Sailing Liberty E85- Retiring on $20 a month in Boot Key Harbor on a Sailboat
Sailing Liberty

Sailing Liberty E85- Retiring on $20 a month in Boot Key Harbor on a Sailboat

Instagram Facebook Page Sailing Liberty Wish List: SUPPORT US ON PAYPAL: [email protected] This video from Sailing Liberty provides an in-depth look at living on a sailboat in Boot Key Harbor, Florida, showcasing the affordable lifestyle and ongoing boat maintenance. The crew hig...
Grenada to Bonaire: Dolphins, Mahi & Midnight Chaos!
Sailing Big Lost

Grenada to Bonaire: Dolphins, Mahi & Midnight Chaos!

We set sail from Grenada to Bonaire on our Vision 444 catamaran for the final leg of our passage west. The trip begins as smooth downwind sailing—perfect conditions, fresh mahi on the grill, dolphins dancing at the bow, and plenty of laughs with our buddy boat. But of course, no sail is complete wi...
Cruising Grenada | Friendships, Challenges & Boat Life
Sailing Big Lost

Cruising Grenada | Friendships, Challenges & Boat Life

This week we share some of the ups and downs of life aboard while waiting for a weather window to sail west. One of the greatest gifts of boat life has been meeting incredible cruising families and watching our kids form lasting friendships—learning to stay connected across distances and rekindling ...
Sailing the Top Island Destinations of Belize
Sailing Banana Pancakes

Sailing the Top Island Destinations of Belize

⛵️Episode 2 of our Belize-Sailing Vacation. We lifted anchor after a rough night of Easton getting impaled by the catfish. He was up bright and early the next morning fishing again. We loaded up in the dinghy and headed into town to get ice as our fridge and freezer were not working. Once we got b...
St Lucia Adventure: Exploring the Majestic Pitons! Episode 45
Sailing Banana Pancakes

St Lucia Adventure: Exploring the Majestic Pitons! Episode 45

Sailing St. Lucia After the Storm | Anniversary, Chocolate & Mud Baths! | Ep. 45| Banana Pancakes We’re back with another unforgettable episode of our sailing adventure—and this one’s packed with tropical storms, wedding anniversaries, chocolate EVERYTHING, volcanic mud baths, and a wild ride t...
The raw and rugged REMOTE ISLANDS you WANT to be STRANDED on – Ep 229
Sailing Jibsea

The raw and rugged REMOTE ISLANDS you WANT to be STRANDED on – Ep 229

Join us on boat life adventures as we island hop sailing from Antigua to Barbuda, exploring endless picture-perfect pink sand beaches before facing the challenge and thrill of getting stranded ashore. We embark on an impromptu overnight sail in our aluminum sailboat to explore the private and remot...
SHE’S A THRILL TO SAIL! – Ep 226
Sailing Jibsea

SHE’S A THRILL TO SAIL! – Ep 226

We embark on a sail from the half French, half Dutch island of of Saint Martin/Sint Maarten to Antigua, covering 100 nautical miles across the Caribbean. We face a winch malfunction shortly after picking up anchor. See how we solve this issue on the go. We sail past a couple other Caribbean islands,...
TEAK & THROTTLE: Custom Yacht Interior & Tohatsu 2 Stroke vs 4 Stroke – Ep 225
Sailing Jibsea

TEAK & THROTTLE: Custom Yacht Interior & Tohatsu 2 Stroke vs 4 Stroke – Ep 225

We're in St. Martin/Sint Maarten in the Caribbean while cruising on our custom aluminum sailboat and working on the teak restoration and varnishing. After restoring the cockpit, we're tackling the wooden interior of our tiny home with final touches. We also celebrate a birthday onboard wh...
Sleeping in a Jungle Treehouse: The Ultimate Adventure! Episode 21
Sailing Banana Pancakes

Sleeping in a Jungle Treehouse: The Ultimate Adventure! Episode 21

“Boat Engine Fails, Jungle Adventures, and a Surf Crush? Dominican Republic Chaos!” Description Rewrite: In this episode, everything goes wrong—and then totally right! 🚤 Our sailboat engine overheats, the anchor won’t drop, and we’re forced to sail back to the marina. But the adventure doesn’t stop...
Let’s BEAT The HEAT- Part 2 –  EZ SNAP (Barefoot Travels S6 E7)
Barefoot Travels

Let’s BEAT The HEAT- Part 2 – EZ SNAP (Barefoot Travels S6 E7)

Barefoot Travels episode shares installing DIY EZ SNAP sun shades to beat the heat in boat windows, reduce UV damage, protect and beautify the interior while keeping it cooler inside.
WE SAILED TO MARTINIQUE FOR CARNIVAL! EP-137
Leading the Escapade

WE SAILED TO MARTINIQUE FOR CARNIVAL! EP-137

CARNIVAL CELEBRATIONS IN MARTINIQUE BY BOAT, WE UNCOVER THE SAD REALITY OF THE RECENT STORM SURGE WITH BOATS WASHED UP ON THE BEACH AND ROCKS, WE DIVE SOME UNDERWATER MERMAID SCULPTURES AND WE SAIL TO DOMINICA! LOVE OUR CONTENT?? Here are the many ways you can support us! 🛍️ Check out our Official...
213. Top Destinations in the BVI’s | Sailing Sunday
Sailing Sunday

213. Top Destinations in the BVI’s | Sailing Sunday

Ahoy, fellow sailors and travelers! Set sail with us on a sun-soaked adventure through the stunning British Virgin Islands, where the crystal clear waters are just the beginning of the excitement! Join us, as we navigate the Caribbean waters of the British Virgin islands, visiting the coolest beach ...
SSL 681~ SwellPro SplashDRONE 4 – Full Review
Captain Rick Moore

SSL 681~ SwellPro SplashDRONE 4 – Full Review

The Ultimate SSL 681~ What the heck is that ?!? Today we test the newest edition of the SwellPro SplashDrone 4 waterproof drone.. will it finally meet expectations where others have failed in the past? Let's find out! ✅Join our Patreon and join our Team SSL Crew! ✅Come and join us realtime...
SSL 680 ~ what’s happened to the Captain?
Captain Rick Moore

SSL 680 ~ what’s happened to the Captain?

In this video, we'll explore the SSL 680 'what's happened to the Captain?' topic. Since the Captain was last seen on the surface of the sun, many questions have arisen. What happened to the Captain? Is he still alive? And where is he? In this video, we'll explore the SSL 68...
Sailing Ama-gi  ⛵️ The island of DEVASTATION 🌋 and BEAUTY 🏝 EPISODE 7 Montserrat    HD 1080p
Sailing Ama-gi

Sailing Ama-gi ⛵️ The island of DEVASTATION 🌋 and BEAUTY 🏝 EPISODE 7 Montserrat HD 1080p

Once a very popular island for tourists, Montserrat is now a shadow of its former self. Join us to see the absolute DEVASTATION and BEAUTY of the island of Montserrat. #sailing #caribbean #montserrat #family #sailingfamily #downsyndrome #ms #livingthedream #bucketlist #followyourdreams #devastat...
Sailing  Ama-gi ⛵️ STUCK IN PARADISE EPISODE 4   HD 1080p
Sailing Ama-gi

Sailing Ama-gi ⛵️ STUCK IN PARADISE EPISODE 4 HD 1080p

⛵️DISASTER averted and #sail DIVERTED to PARADISE. 🏝️Come join us on our attempt to sail from #saintjohn to 🇻🇮 #stmaarten 🇫🇷This #family does NOT give up.💕 #abilities #caribbean #downsyndrome #family #sailing #sailingfamily #ms #travel #travelingfamily
New Catamaran Owners Trust “the Professionals”… – Ep 81
Sailing Jibsea

New Catamaran Owners Trust “the Professionals”… – Ep 81

We help new sailors and Lagoon 440 owners tow their catamaran from the Dutch Caribbean island of St. Maarten to the French island of Saint Martin. Their catamaran has no auxiliary power, meaning it has no engines. We go through shallow spots, dodge ship wrecks and use small inflatable dinghies to t...
Why Living on a Sailboat does NOT mean Living off the Sea…Plus: Dinghy Repair – Ep 77
Sailing Jibsea

Why Living on a Sailboat does NOT mean Living off the Sea…Plus: Dinghy Repair – Ep 77

This week we tour a popular tourist destination and cruise ship port in Philipsburg, Sint Maarten where we explore the famous duty-free boardwalk before returning back to our monohull sailboat and show the challenges in cooking in the galley and what living on a sailboat can bring. Lastly, we show ...
Sailing to TEENY TINY ISLANDS we Never Knew Existed in GUADELOUPE! – Ep 70
Sailing Jibsea

Sailing to TEENY TINY ISLANDS we Never Knew Existed in GUADELOUPE! – Ep 70

Thanks to Skillshare for sponsoring this episode. The first 1,000 people to use this link will get a 1 month free trial of Skillshare: We enjoy a beautiful sail our Hunter sailboat to a group of small (and some uninhabited) islands we never knew existed! We hike, explore ruins, penitentiaries and...
Quarantining Didn’t Go As Expected, UNDERWATER ART & BOAT WORK – Sealing a LEAKING HATCH – Ep 42
Sailing Jibsea

Quarantining Didn’t Go As Expected, UNDERWATER ART & BOAT WORK – Sealing a LEAKING HATCH – Ep 42

We've arrived in Grenada where we will be spending most of hurricane season. We initiate the check in and quarantine process in Grenada They lost our PCR test samples so we're stuck on our boat for much longer than we're supposed to be! We should have only quarantined for 2 days, b...
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