Watch Sailing & Boating Adventures Around the World – Page 25 of 111

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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Rescued At Sea: Boat Adrift in Open Ocean. Episode 43
Sailing Banana Pancakes

Rescued At Sea: Boat Adrift in Open Ocean. Episode 43

From Chaos to Kindness | Sailing from Dominica to Martinique (ft. Engine Trouble, Mahi & a Rescue!) We left Dominica with over 20 knots of wind and immediately broke a cleat holding the Genoa—then the Genoa took out our light. Welcome to offshore sailing! Rough seas, tangled lines, and flying f...
Gone with the Wynns Getting Rid of Their HH Catamaran! – Ep 322 – Lady K Sailing
Lady K Sailing

Gone with the Wynns Getting Rid of Their HH Catamaran! – Ep 322 – Lady K Sailing

I love watching gone with the Wynns! They’re such an amazing couple out there doing the sailing thing to the fullest extend a couple can. Like Delos, they’ve got no boundaries as they sail everywhere in the world they can find water but today, after a long and somewhat disastrous experience with the...
Komodo National Park Like You’ve Never Seen It | S4 E7
Sailing with six

Komodo National Park Like You’ve Never Seen It | S4 E7

This week on Sailing with Six, we explore Komodo National Park like you’ve never seen it—anchoring in crystal-clear waters, hiking barren island hills, snorkelling vibrant reefs, and setting out on our own DIY dinghy tour to find the elusive Komodo dragon. 🐉🏝️ We’re anchored at Pulau Sebayur Besar,...
Boat Life ⛵ She needs to Catch her Own Food! 🐟 Ep. 137
Sailing SV CUBA

Boat Life ⛵ She needs to Catch her Own Food! 🐟 Ep. 137

This is what boat life is all about! In this episode you get to see the real life of sailing around the world and how we live full time and living off-grid We're sailing around the world, and with your support, we will fund better cameras, the internet to upload videos, and of course, the occa...
I Turned 70 Today—And Here’s Why It Matters #vernalequinox #birthday #sailing #japan
Japan Solo

I Turned 70 Today—And Here’s Why It Matters #vernalequinox #birthday #sailing #japan

March 20th isn’t just another day on the calendar—it holds deep personal meaning for me. It marks the Vernal Equinox, a symbol of balance, renewal, and fresh starts. On this day 25 years ago, I began a life-changing 3,000 km bicycle journey from Sakurajima in Kyushu to Hokkaido—a personal challenge...
Sailing 500 miles to the CANARY ISLES on a small boat
Sailing Maalie

Sailing 500 miles to the CANARY ISLES on a small boat

Jump on board with us with extra content AND ad-free videos ~ Support our Production▸ After a long descent of western Europe, we are now well placed to push off in to the Atlantic Ocean and head for the first stepping stone on this route. There is a good forecast of trade-winds and we get to proper...
[Ep 3] We Moved Onto a 43 Foot Sailboat!
SmoCo Sailing

[Ep 3] We Moved Onto a 43 Foot Sailboat!

In this episode we flashback to 2023 when we sold all of our furniture (and more) and moved from our 2 bedroom apartment onto our 43 ft sailboat. This was a hectic month with Liya still recovering from ankle surgery, both of us working full-time, traveling for work, and doing military reserve duty p...
In search of The Last True Sailors of the Caribbean | Epic Journey (E.136)
Sailing SV CUBA

In search of The Last True Sailors of the Caribbean | Epic Journey (E.136)

Join us on an epic journey across the Caribbean as we track down the last true sailors—masters of the sea, tradition, and adventure. Don't miss. Follow us every week in our real life sailing adventure, as we live off grid, sail from place to place, travel from country to country discovering ne...
TERRIFYING Sailboat Rescue in Puget Sound – ep 321 – Lady K Sailing
Lady K Sailing

TERRIFYING Sailboat Rescue in Puget Sound – ep 321 – Lady K Sailing

Mayday 7 p.m. on Monday, Feb. 3 In a news release, the Coast Guard noted there was snowy conditions and 25 to 30 mph winds with 4 to 6-foot seas that night. "As Coast Guard crews were attempting the rescue, the sailboat ran aground. After the mast of the vessel collapsed, the aircrew was able t...
FOR SAIL: Beneteau Oceanis 40 – 2007, 2 cabins version
Ryan & Sophie Sailing

FOR SAIL: Beneteau Oceanis 40 – 2007, 2 cabins version

They say that the happiest days of boat ownership are when you buy your boat and when you sell it. Well, let us tell you: this is wrong! ;) Read more about Polar Seal at: We are a little sad about our decision to part with our girl, but life is currently taking us in a direction that doesn’t allo...
We SAILED to a creepy ABANDONED Hotel on the Brazilian Coast — Sailing Yabá 263
Sailing Yabá

We SAILED to a creepy ABANDONED Hotel on the Brazilian Coast — Sailing Yabá 263

Episode 263 | Sailing to an abandoned haunted hotel ⛵ *Hop aboard & follow our journey* → SUBSCRIBE 💙 *Support the adventure:* 📖 *Grab our book* → 🌊 *Join our crew on Patreon* → Exclusive content here: ☕ *Send us a drink* → via PayPal: 🧢 *Shop our gear* → Coolest T-shirts and hats here: ...
From Famine to Feast – Did We Just Teleport Here?! | S4 E6
Sailing with six

From Famine to Feast – Did We Just Teleport Here?! | S4 E6

From Famine to Feast – Did We Just Teleport Here?! After weeks in remote Indonesia, where supplies were scarce and luxuries nonexistent, we sailed into a whole new world—Flores. Suddenly, we had access to fresh produce, coffee, and foods we hadn’t seen in months! Join us as we explore the vibrant t...
Exploring the Island of Dominica: Hikes, Waterfalls, River Boat tour. Episode 42
Sailing Banana Pancakes

Exploring the Island of Dominica: Hikes, Waterfalls, River Boat tour. Episode 42

Exploring Dominica: Waterfalls, Jungle Hikes & Our Last Adventure! 🌿💦⛰️ Join us for our last day in the lush jungle of Dominica! We started our morning packing up our VRBO and heading out for an adventure. First stop: Emerald Pool—a stunning waterfall with crystal-clear water. While Steve and t...
Painting Over Wood, No Turning Back. Making Huge Progress On Our Boat Interior Renovation.
SailorBarry

Painting Over Wood, No Turning Back. Making Huge Progress On Our Boat Interior Renovation.

Welcome to season 3 of Sailor Barry & Hailly This week we’re making huge changes down below decks, come check it out! Support: Patreon: PayPal: Buy Us A Beer!!: Total Boat X Sailor Barry Affiliate Link Wet edge topside paint Gleam Varnish - Barry - Hailly Amazon WishList!: #boa...
🌊 Living the Ocean Nomad Life – Discovering a Hidden Island Paradise! 🏝️✨ E.135
Sailing SV CUBA

🌊 Living the Ocean Nomad Life – Discovering a Hidden Island Paradise! 🏝️✨ E.135

Join me on an epic adventure as I embrace the ocean nomad life, sailing to a hidden island paradise! 🏝️🌊 Crystal-clear waters, untouched beauty, and pure freedom. Let’s explore! 🚤✨ Follow us every week in our real life sailing adventure, as we live off grid, sail from place to place, travel from co...
The INSANE Aft Cabin Center Cockpit Hunter Passage 420
Lady K Sailing

The INSANE Aft Cabin Center Cockpit Hunter Passage 420

Caribbean and Bahamas live aboard sailing take a long time to plan but, what if you could buy a great cruising sailing today in Florida and be in the Bahamas tomorrow? This week we look at a sailboat for sale right now fully outfitted and rigged for Caribbean live aboard sailing you can buy for less...
Leaving Okinawa for Kyushu by Sailboat #sailing #okinawa #japan
Japan Solo

Leaving Okinawa for Kyushu by Sailboat #sailing #okinawa #japan

The journey north begins! After 15 months, my boat is finally back in Kyushu, marking the start of Chasing the Cherry Blossom 2 – a voyage following Japan’s iconic Sakura season by sea. Leaving Itoman, I planned to sail overnight to Amami, but as I passed Ieshima, in discussion with Ian, I decided t...
Sailing 50 Tons Upwind: Can We Even Make It? (Honest Review) — Sailing Yabá 262
Sailing Yabá

Sailing 50 Tons Upwind: Can We Even Make It? (Honest Review) — Sailing Yabá 262

Episode 262 | Sailing our 50-ton boat upwind for the first time. Will that work? ⛵ *Hop aboard & follow our journey* → SUBSCRIBE 💙 *Support the adventure:* 📖 *Grab our book* → 🌊 *Join our crew on Patreon* → Exclusive content here: ☕ *Send us a drink* → via PayPal: 🧢 *Shop our gear* → Coole...
Worst STORM We’ve Had – 40+knots and BARE POLES | S4 E5
Sailing with six

Worst STORM We’ve Had – 40+knots and BARE POLES | S4 E5

From Calm to Chaos—We Did NOT See This Coming! It's the worst storm we’ve had with 40+knots and running off with bare poles. This was supposed to be a straightforward passage—two nights at sea, motoring across glassy waters, dodging the usual FADs (fish aggregating devices). But then, out of n...
[Ep 1] Buying a Sailboat: Will We Sail Away or Sink Deep Into Regret?
SmoCo Sailing

[Ep 1] Buying a Sailboat: Will We Sail Away or Sink Deep Into Regret?

We’re 2000 miles into our journey, but we’re backtracking on Youtube to give our friends and family a glimpse into how our crazy idea turned into a plan, then into reality. In this episode we flashback to purchasing the first sailboat we saw and the 200 mile sail to bring her home to Monterey where ...
We Sailed to the Most Unexplored Island in the Caribbean – THE WILD QUEEN 🌋🩵E.134
Sailing SV CUBA

We Sailed to the Most Unexplored Island in the Caribbean – THE WILD QUEEN 🌋🩵E.134

Secure your privacy with Surfshark! Go to for an extra 4 months Follow us every week in our real life sailing adventure, as we live off grid, sail from place to place, travel from country to country discovering new adventures. *Want to support us?" Patreon: Buy Salsa a Coffee☕🧡: Amazon Wis...
Grenada Sailboat HIJACKING – Ep 319 Lady K Sailing
Lady K Sailing

Grenada Sailboat HIJACKING – Ep 319 Lady K Sailing

Learning from tragedy is important. Two Americans, a sailing couple are presumed dead after they vanished from their yacht in Grenada, leaving behind evidence of a bloody struggle, police in nearby St. Vincent and the Grenadines said Monday. While loved ones of Kathy Brandel and Ralph Hendry are hop...
Living the Dream⛵🌊 Sailing, Diving, Kitesurfing… and endless Boat Work!— Sailing Yabá 261
Sailing Yabá

Living the Dream⛵🌊 Sailing, Diving, Kitesurfing… and endless Boat Work!— Sailing Yabá 261

Episode 261 | Sailing, diving, kitesurfing and... fixing stuff! ⛵ *Hop aboard & follow our journey* → SUBSCRIBE 💙 *Support the adventure:* 📖 *Grab our book* → 🌊 *Join our crew on Patreon* → Exclusive content here: ☕ *Send us a drink* → via PayPal: 🧢 *Shop our gear* → Coolest T-shirts and h...
Parasailor vs. Spinnaker – which is the BEST for Sailing the WORLD?
Sailing with six

Parasailor vs. Spinnaker – which is the BEST for Sailing the WORLD?

Parasailor vs. Spinnaker - which is the BEST for Sailing the WORLD? Is a Parasailor really the ultimate downwind sail, or have we been missing out on something better? In this episode, we put our beloved Big Red (Parasailor) head-to-head with a brand-new Purple (Cruising Spinnaker) to see which one...
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