Watch Sailing & Boating Adventures Around the World – Page 10 of 144

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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The RAGGED ISLANDS have it all [E360]
Wildly Intrepid Sailing

The RAGGED ISLANDS have it all [E360]

The remote islands in the Bahamas are hidden gems. We enjoy all sorts of activities from snorkeling, spearfishing, wing foiling, potlucks, dinghy adventures, pigeon tours and so much more. Hog Cay, Raccoon Cay and Ragged Island are amazing places to cruise to. Filmed Winter 2025. If you like what y...
What goes overboard? Sailing to & checking into Costa Rica
Sailing Catalpa

What goes overboard? Sailing to & checking into Costa Rica

This week we are sailing to check in to Costa Rica it’s a chaotic sail where something goes overboard. Need a ESIM Get a 5% discount with Holafly here To get 20% off Florence Marine use the code 20CATALPA072 Cheers everyone for watching!! Subscribe @SailingCatalpa Become a Patron To DONA...
ROBBED! How We Were Targeted by Thieves
Gone with the Wynns

ROBBED! How We Were Targeted by Thieves

We’ve traveled for over a decade without anything like this ever happening… until now. Robbed in Amsterdam. ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video Gear 📷 📱Socials INSTAGRAM: FACEBOOK: 📧EMAIL notifications, so you never miss a video🍦 🎶 MUSIC for vids. 2 Months...
It all changed so fast… [E359]
Wildly Intrepid Sailing

It all changed so fast… [E359]

We've stumbled onto paradise at Hog Cay, from hikes to paddleboarding and epic spearfishing this island has it all. However a short sail over to Ragged Island turns into a very eventful day! Filmed Winter 2025. If you like what you see don't forget to give us the thumbs up! #sailing #sai...
Living on my Sailboat Changed how I see the World! E163 – This is Where I Live Today!
Sailing SV CUBA

Living on my Sailboat Changed how I see the World! E163 – This is Where I Live Today!

Living aboard my sailboat has completely transformed my perspective on life! ⛵ In this Episode, I take you on a tour of where I live today and share what it’s like to embrace the sailing lifestyle, live full-time on a sailboat, and explore the world from the water. Wish to support our journey so w...
Trinidad Yacht Life: Navigating Geopolitical Tension while Upgrading Our Sailboat
Travel Sketch

Trinidad Yacht Life: Navigating Geopolitical Tension while Upgrading Our Sailboat

Despite the backdrop of geopolitical tension, boat life goes on with the continuing construction of our custom carbon fiber yacht tables. Now that they've been painted with gel coat, it's time for me to get sanding, shaping the gel coat. As always though, nothing on a sailing boat is simpl...
Back in the Water! From Boatwork to Tan Lines — Sailing Life Returns  E.162
Sailing SV CUBA

Back in the Water! From Boatwork to Tan Lines — Sailing Life Returns E.162

After weeks in the boatyard, our sailboat is finally back in the water! In this episode, we leave the nonstop boatwork behind and return to real cruising life—sunshine, tan lines, and the freedom of sailing again. Join us as we relaunch, test everything onboard, and get back to exploring the islands...
Sohamo M3 Fat Tire Ebike | SailAway Reviews
SailAway World Sailing

Sohamo M3 Fat Tire Ebike | SailAway Reviews

An all-around workhorse of an off-road fat tire e-bike! Enjoy!! Thanks for watching SailAway, the travel documentary of an adventurous sailing couple, kid and dog, sailing the world! [JOIN OUR CREW] Appreciate our videos? Then join our crew as a Patreon Patron and get FREE SailAway GEAR plus o...
TST Carrier E-bike | SailAway Reviews
SailAway World Sailing

TST Carrier E-bike | SailAway Reviews

The SUV of ebikes! Enjoy!! Thanks for watching SailAway, the travel documentary of an adventurous sailing couple, kid and dog, sailing the world! [JOIN OUR CREW] Appreciate our videos? Then join our crew as a Patreon Patron and get FREE SailAway GEAR plus other perks, all while helping us stri...
Fun times at Double-Breasted Cay and Buenavista [E358]
Wildly Intrepid Sailing

Fun times at Double-Breasted Cay and Buenavista [E358]

When two girls meet up it's adventure time. After a rough night and morning at Water Cay, we sail South with dolphins to Buenavista in the Ragged Islands. There we find yet another paradise for snorkeling, spearfishing and wing boarding. We reunite with a family we've met back at the marin...
We Won A $2M Boat At Auction
Gone with the Wynns

We Won A $2M Boat At Auction

We bought an Explorer Yacht on AUCTION! Go to or use code WYNNS at checkout to get 4 extra months of Surfshark VPN! ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video Gear 📷 📱Socials INSTAGRAM: FACEBOOK: 📧EMAIL notifications, so you never miss a video🍦 🎶 MUSIC for vids. ...
When Your Sailing Plans and Budget Corrode in front of You – E.161 – Sailing SV CUBA
Sailing SV CUBA

When Your Sailing Plans and Budget Corrode in front of You – E.161 – Sailing SV CUBA

Our safety, sailing plans, budget and nerves are crumbling in this episode, but you gotta suck it up and keep smiling, with the hope that things will get better.
[Ep 38] Jib Furler Saga Finale & Farewell to Baja (For Now)
SmoCo Sailing

[Ep 38] Jib Furler Saga Finale & Farewell to Baja (For Now)

Episode 38 If you've followed us since around episode 20 when we had our rigging professionally replaced in San Diego, you've seen us struggle with the jib furler. It's crazy that it's taken us this long to figure out the solution and how many jib halyards we shredded before ever...
What Happens If You Drop Anchor in the Wrong Spot?
Dylan Magaster

What Happens If You Drop Anchor in the Wrong Spot?

Get Captain's Salve: A routine sailing trip quickly became a challenge when swim bouys were laid directly in front of the boat, tangling the anchor rope. This video captures the intricate process of trying to retrieve the anchor while ensuring the boat remains stationary and the tow float unha...
We are Boatless… NOW WHAT?! | Sailing Sunday Vlog 301
Sailing Sunday

We are Boatless… NOW WHAT?! | Sailing Sunday Vlog 301

With “Sunday” officially sold, we pack up our little family, squeeze into a 5th wheel and hit the road from Florida to the Annapolis Boat Show. It’s our first big trip as boatless sailors. Just us, the baby, the dog and a whole lot of “what now?!” We explore the Boat show, hug our Patreons and Sub...
Hammerheads and Tiger Sharks [E357]
Wildly Intrepid Sailing

Hammerheads and Tiger Sharks [E357]

A fascinating array of sea life, including hammerheads, tiger sharks, and numerous fish, was not what we expected in the Jumentos Islands. There are also ocean holes and stunning beaches, which are great for kids to play on and offer perfect conditions for paddleboarding. Our time at Water Cay is fl...
We Sold Our Boat After 7 Years in Our Tiny Home on Water | Sailing Sunday Vlog 300
Sailing Sunday

We Sold Our Boat After 7 Years in Our Tiny Home on Water | Sailing Sunday Vlog 300

Seven years aboard our Tiny Home on Water sailing 45,000+ nautical miles, in five minutes, It was Sold!!! That’s how long it took for a subscriber to buy our floating home after we advertised "Sunday" For Sale! BUT, Today it’s official! the survey, sea trial, the signatures and our hardest...
New Boat, Baja 1000 & Sailing Antarctica!
Gone with the Wynns

New Boat, Baja 1000 & Sailing Antarctica!

BIG Adventures Ahead! Shop Beam’s Black Friday Sale! Get up to 50% off with my link: (limited time only!). No code needed - discount will auto apply at checkout! Sailing Antarctica! More about Captain Cathrine and our Expedition to Antarctica: Baja 1000 If you want to see the schedule and race m...
Sailing to REMOTE Jumentos Islands [E356]
Wildly Intrepid Sailing

Sailing to REMOTE Jumentos Islands [E356]

We escape the hustle and bustle of Georgetown and make a run to Long Island. Hiding from 30+ knots winds in Thompson Bay makes it the perfect place to reunite with some friends. Soon after we finally cross to the remote islands of the Jumentos. A few minutes after dropping anchor and we are already ...
E355 Happiness is best when shared in the BAHAMAS
Wildly Intrepid Sailing

E355 Happiness is best when shared in the BAHAMAS

Trying to tell someone how we live full-time on a sailboat and what it feels like is nearly impossible. The best solution is to share it. And we couldn't be luckier because we just get to do this with Alex's brother, nephew and niece. We give them the real Bahamian cruising life experience...
Our Tiny Home on Water: THE LAST SAIL | St. Marys, Georgia Vlog: 299
Sailing Sunday

Our Tiny Home on Water: THE LAST SAIL | St. Marys, Georgia Vlog: 299

We have been living aboard for 7 years, sailing half way around the world over 40,000nm and this week we head off shore for our final passage with our tiny home sailing into St. Marys, Georgia, USA to meet the (potential) new owners! But, before anything’s “official,” we arrive and explore the stree...
I Came Home… and He Was Gone | Sailing Avocet
Sailing Avocet

I Came Home… and He Was Gone | Sailing Avocet

Marissa left for California to get some work and snowboarding in, then returned home to a boat without Chris! @KesselUnderway sailed away to La Cruz, leaving Marissa alone aboard for a week where she quickly realized she is bad at being alone, and even worse at learning to love the isolation of the ...
Another Boat Problem, Another Lesson Learned – E.159 – Sailing SV CUBA
Sailing SV CUBA

Another Boat Problem, Another Lesson Learned – E.159 – Sailing SV CUBA

Another boat fix, another story to tell. Nothing goes to plan — but that’s sailing for you! You buy a sailboat and dream of sailing around the world, but end up fixing your sailboat all over the world. ☹️ Did I miss something?
[Ep 34] Sailing into Turquoise Waters & Exploring Islands in the Sea of Cortez
SmoCo Sailing

[Ep 34] Sailing into Turquoise Waters & Exploring Islands in the Sea of Cortez

Episode 34: Exploring Ensenada el Cardonal on Isla Partida & Ensenada del Gallo on Espiritu Santo After leaving La Paz, we sail north into the wild side of the Sea of Cortez. Our first stop: Ensenada del Gallo, a quiet anchorage surrounded by mangroves and tidal flats where strong winds keep us...
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