Watch Sailing & Boating Adventures Around the World – Page 4 of 67

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 73-96 of 1594 results
Rugged expedition meets cozy liveaboard comfort: UPDATED CUSTOM BOAT TOUR – Ep 269
Sailing Jibsea

Rugged expedition meets cozy liveaboard comfort: UPDATED CUSTOM BOAT TOUR – Ep 269

This episode is an updated boat tour of our custom designed aluminum sailboat Jibsea II after owning her for almost two years. We detail how we've refit her and showcase the marine upgrades we've made to ensure creature comforts while full time cruising anywhere in the world, from sailing ...
Solo Sailing to the Cave of the Apocalypse | Patmos
Dylan Magaster

Solo Sailing to the Cave of the Apocalypse | Patmos

Today I am solo sailing through the aegean sea to the island of Patmos, Greece. This single-handed sailing adventure is about 40 nautical miles beating to windward and a rough sail. Support on Patreon: Support with Bitcoin: 1C2GuZPscVskvzScBJSQpdeXqGz2moJHaC Follow Dylan Magaster: Business inqui...
Why Would Anyone Want a Trimaran?
Lady K Sailing

Why Would Anyone Want a Trimaran?

Why would anyone choose a trimaran over a monohull? In this video, we compare the Dragonfly 36 trimaran vs a Beneteau Oceanis 40.1 to answer one of sailing’s biggest questions: are trimarans better than monohulls? We break down trimaran vs monohull pros and cons, including speed, stability, comfort,...
Why Are Whales Sinking Sailboats?
Lady K Sailing

Why Are Whales Sinking Sailboats?

Why are whales sinking sailboats? Over the last few years, reports of orcas attacking sailboats have exploded across the sailing world, particularly off the coasts of Spain, Portugal, and the Strait of Gibraltar. Sailors have reported killer whales targeting rudders, disabling steering, and in some ...
Why Most People Quit Living on a Sailboat
Lady K Sailing

Why Most People Quit Living on a Sailboat

Living on a sailboat sounds amazing… until reality sets in. In this video, we talk honestly about why most people quit living on a sailboat. Not the romantic Instagram version. The real, day-to-day challenges that catch people off guard and slowly wear them down. If you’re thinking about: • living o...
Sailing and Spearfishing at the Edge of the World
Dylan Magaster

Sailing and Spearfishing at the Edge of the World

Support on Patreon: Support with Bitcoin: 1C2GuZPscVskvzScBJSQpdeXqGz2moJHaC Follow Dylan Magaster: Business inquires or music submissions: [email protected] Music: Filmed by Dylan Magaster: Edited by Dylan Magaster:
The Cheapest Modern Sailboats You Can Actually Live On
Lady K Sailing

The Cheapest Modern Sailboats You Can Actually Live On

Can you live on a sailboat if you’re not a sailor? Yes. And it doesn’t have to be expensive, old, or uncomfortable. In this video, we’re talking about the cheapest modern sailboats you can actually live on. Not performance boats. Not ocean-crossing yachts. Just modern, affordable, floating homes tha...
Free Sailboat Living The Only Way It Actually Works
Lady K Sailing

Free Sailboat Living The Only Way It Actually Works

Can you really live on a sailboat for free? Not the Instagram fantasy version — the real, practical version. In this video, we break down how people actually live on sailboats for little to no monthly cost, using real systems that work in the real world. This isn’t about hacks or shortcuts. It’s ab...
A $5,000 Sailboat Can Cost You $40,000 – Ep 371 – Lady K Sailing
Lady K Sailing

A $5,000 Sailboat Can Cost You $40,000 – Ep 371 – Lady K Sailing

So you found a $5,000 sailboat. It floats. It has a mast. The owner says “just needs a little TLC.” What could possibly go wrong? In this episode of Lady K Sailing, we break down the real numbers behind “cheap” sailboats. Standing rigging replacement, new sails, chainplates, soft deck repairs, bu...
Sailing and Spearfishing in the Aegean Sea | Koufonisia
Dylan Magaster

Sailing and Spearfishing in the Aegean Sea | Koufonisia

Join us on a sailing trip around the stunning Naxos and Koufounissia in the Cyclades, Greece, showcasing the beautiful "sailing cyclades" experience. We navigate past the large island of Naxos, anchoring in the protected bay of Panarmos, a perfect example of "sailing greece" and ...
The Big Problem With Beneteau (It’s Not What You Think)
Lady K Sailing

The Big Problem With Beneteau (It’s Not What You Think)

Are Beneteau sailboats really “bendy,” cheap, or unsafe — or is the internet just yelling again? If you’re a middle-aged couple thinking about selling the house, buying a sailboat, and cruising to the Bahamas or the Caribbean, chances are a Beneteau is already on your shortlist. They’re everywhere ...
My First ever Catch and Cook with a rusty Speargun
Dylan Magaster

My First ever Catch and Cook with a rusty Speargun

First-time spearfishing while living on a sailboat in Greece — freediving in the Aegean Sea near Naxos and Rineia to catch wild fish for food using a speargun, including white trevally and triggerfish, then cleaning, filleting, and cooking fresh seafood at anchor as part of an off-grid sailing lifes...
Taswell: The Secret Bluewater Yacht Built Like an Oyster
Lady K Sailing

Taswell: The Secret Bluewater Yacht Built Like an Oyster

Are Taswell yachts the best-kept secret in bluewater cruising? In this video, we take a deep dive into Taswell yachts and compare them directly to one of the most respected names in offshore sailing: Oyster Yachts. Using real-world listings, we show how a Taswell 56 can sell for hundreds of thousan...
No One Wants This ISLAND PACKET 44! Ep 367 – Lady K Sailing
Lady K Sailing

No One Wants This ISLAND PACKET 44! Ep 367 – Lady K Sailing

The boat for sale: Why is a 44-foot bluewater cruising sailboat priced so low? In this video, we take a deep dive into a 1994 Island Packet 44 that looks suspiciously cheap for its size, reputation, and offshore capability. Island Packet sailboats are known for being strong, conservative, full-ke...
Goodbye Catalina The End of America’s Favorite Sailboat Brand
Lady K Sailing

Goodbye Catalina The End of America’s Favorite Sailboat Brand

For decades, Catalina Yachts was the front door to sailing in North America. If you learned to sail, cruised your first coastline, or ever thought “maybe this could be my life,” there’s a good chance a Catalina was involved. But right now, Catalina isn’t building boats. Production has paused. The ...
When back ups become the plan – offshore sailing to Scotland – Ep 264
Sailing Jibsea

When back ups become the plan – offshore sailing to Scotland – Ep 264

Join us as we prepare to sail offshore in the North Atlantic in our custom aluminum sailboat from the nordic region of the Faroe Islands to Scotland, United Kingdom. We tackle failed Raymarin electronics, life on passage in the North Atlantic before dropping the hook in the beautiful outer hebrides!...
Step aboard MUSHU for a glimpse into our world on the water. ⚓✨
Captain German Exploring

Step aboard MUSHU for a glimpse into our world on the water. ⚓✨

Ever wondered what daily life looks like when your home is a sailboat? In this video, we’re taking you along for a full day of yachting routine—from the quiet magic of morning coffee on deck to the satisfying (and sometimes oily) reality of boat maintenance. What’s inside: • Sunrise rituals and bre...
I Might Need a New Engine
Sailing With Phoenix | Oliver

I Might Need a New Engine

The white smoke still won’t quit. I’m going deeper now and gambling $1,600 on a set of new fuel injectors. If this doesn’t work, I could be staring down a full engine replacement. ⛵ Join the Crew + Follow Along: 🌐 All My Links 📍 Live Tracker – Where’s Phoenix Now? 👕 Official Merch 📸 Instagra...
WHICH WOULD YOU TAKE? Ep 366 – Lady K Sailing
Lady K Sailing

WHICH WOULD YOU TAKE? Ep 366 – Lady K Sailing

If you woke up tomorrow and won a sailboat lottery, but the prize wasn’t cash… it was a choice between two very different 47-foot sailboats, what would you do? In this video, we dig into a question that accidentally went viral on Facebook: Island Packet 439 or Beneteau Oceanis 47? Same size. Very...
A Rare Dutch-Built Classic | 1961 Bill Tripp Javelin 38 | $49,500! | Tour
BoatFools Sailing

A Rare Dutch-Built Classic | 1961 Bill Tripp Javelin 38 | $49,500! | Tour

#ClassicSailboat #BluewaterSailboat #BillTripp #boatfoolssailing A Rare Dutch-Built Classic | 1961 Bill Tripp Javelin 38 | $49,500! | Tour This Dutch-built Beauty is in San Rafael, CA, so if you're on the west coast and in the neighborhood, go check her out! Welcome back BoatFools Nation! T...
Why is this Catamaran So CHEAP? – Ep 365 – Lady K Sailing
Lady K Sailing

Why is this Catamaran So CHEAP? – Ep 365 – Lady K Sailing

Why is this catamaran so cheap? 🤔⛵ Today we’re taking a deep, honest look at a Fountaine Pajot Mahé 36 Evolution, a real cruising catamaran that can sometimes be found for a shockingly low price compared to newer multihulls. Fountaine Pajot is one of the most respected catamaran builders in the wor...
These 4 Designers Built the Best Sailboats Ever – Lady K Sailing – Ep 364
Lady K Sailing

These 4 Designers Built the Best Sailboats Ever – Lady K Sailing – Ep 364

Most sailboats are not accidents. They are the result of a few brilliant minds who figured out how to turn wind into speed, safety, and beauty. In this video, we break down the four sailboat designers who shaped sailing as we know it — the men whose ideas still influence the boats we buy, sail, and...
why these tricky seas are worth sailing – Ep 262
Sailing Jibsea

why these tricky seas are worth sailing – Ep 262

Join us as we cruise deep into the fjords of the Faroe Islands - part it the United Kingdom of Denmark. We sail into the island of Borðoy where we explore Klaksvik and its jaw dropping beauty. We go on adventures hiking, to the famous Klakkur summit , wild landscapes and mountain views overlooking t...
Learning to Sail: 5 Things I Wish Someone Told Me on Day One – Lady K Sailing – Ep 363
Lady K Sailing

Learning to Sail: 5 Things I Wish Someone Told Me on Day One – Lady K Sailing – Ep 363

Sailing for beginners is a minefield of mistakes. You're watching the wrong videos. Most sailing advice skips the painful, embarrassing realities of Day One. I’ve sailed for years, and these 5 crucial things would have saved me thousands of dollars and years of struggle. Docking is terrifying. ...
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