Watch Sailing & Boating Adventures Around the World – Page 5 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.

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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. ...
The Worst Catamaran Ever Made (The Wildcat 350 Controversy) – Ep 362 – Lady K Sailing
Lady K Sailing

The Worst Catamaran Ever Made (The Wildcat 350 Controversy) – Ep 362 – Lady K Sailing

Thinking about buying a Wildcat 350? Or just curious why this catamaran sparks so much controversy? In this video, we dive deep into the infamous Wildcat 350, the South-African-built catamaran with a reputation that swings wildly between “underrated gem” and “floating science experiment.” I found o...
Safest OLD Sailboats – Ep 361 – Lady K Sailing
Lady K Sailing

Safest OLD Sailboats – Ep 361 – Lady K Sailing

What are the safest old sailboats ever built? In today’s episode of Lady K Sailing, we break down five legendary, storm-tested, ocean-crossing classics that earned their reputations the hard way. These boats aren’t about luxury or modern styling — they’re about survival, stability, and real offshore...
Splash Day Gone Wrong!
Chesca & Ben

Splash Day Gone Wrong!

After 6 months of work, our 40ft sailboat is finally ready to go back in the water after 4 years of being on the hard, but not everything goes to plan. Our new 460Ah FogStar Batteries - Check out FogStar and everything they have to offer here - 🚢 Join Our Crew on Patreon - Want to support our ...
45 GRUELING HOURS OFFSHORE that almost broke us – Ep 260
Sailing Jibsea

45 GRUELING HOURS OFFSHORE that almost broke us – Ep 260

In this episode, we depart Seyðisfjörður, Iceland in late September to begin an offshore sail to the Faroe Islands along a historic North Atlantic route. What started as a routine passage quickly turned into a demanding crossing that tested our endurance and seamanship. We share the realities of off...
Everyone Should Own a Sunfish (Here’s Why) – Ep 360 – Lady K Sailing
Lady K Sailing

Everyone Should Own a Sunfish (Here’s Why) – Ep 360 – Lady K Sailing

The Sunfish is the best-selling sailboat of all time — over half a million built — and for good reason. It’s simple, portable, affordable, nearly indestructible, and one of the purest ways to learn and love sailing. Today, I’m diving into why the Sunfish became a legend, why it’s still one of the mo...
Tables Are Ready for Hinges But There’s a Problem!
Travel Sketch

Tables Are Ready for Hinges But There’s a Problem!

Over the past few weeks we've been sharing the process of building custom carbon fiber tables for our sailing home. Our Leopard 45 hasn't had a rear cockpit table in over a year, thanks to yet another warranty fail from Leopard Catamarans, who sent out a totally new one from the boat build...
Yacht People Problems Part III: Mice
BoatFools Sailing

Yacht People Problems Part III: Mice

#boatfoolssailing #yachtpeopleproblems #mice The annual battle against the dreaded boat mouse is back, as we tackle how to stop them from chewing through our rigging during the colder months. This week, we share a clever hack to winterize your boat effectively and protect those halyards. If you�...
This $59,900 Sailboat Is READY to Sail Away Today! – Ep 359 – Lady K Sailing
Lady K Sailing

This $59,900 Sailboat Is READY to Sail Away Today! – Ep 359 – Lady K Sailing

Today we’re taking a deep dive into one of the best budget bluewater sailboats on the market: a 1984 Tayana 37 listed for $59,900. Yes… a real, offshore-ready, world-capable cruiser for under $60K — and you could quite literally buy it today and sail the Caribbean this season. In this video, we’ll ...
Perfect $20,000 Sailboat (Catalina 30 Refit on a Budget) – Ep 358 – Lady K Sailing
Lady K Sailing

Perfect $20,000 Sailboat (Catalina 30 Refit on a Budget) – Ep 358 – Lady K Sailing

Could you really live on a sailboat for just $20,000? In this episode, we’re building the perfect budget cruiser — the legendary Catalina 30 — and transforming it into a self-sufficient liveaboard for under twenty grand. We’re adding 800 watts of solar power, a 300 amp-hour lithium battery, fixing ...
3 MAJOR Sailboat UPGRADES in One Week
Chesca & Ben

3 MAJOR Sailboat UPGRADES in One Week

In this weeks video we have 3 major upgrades happening which means we are finally able to plan out splash date. Come and check out what we have been up to from increasing our power set, fitting new fabric and a big install below the sailboat. Our new 460Ah FogStar Batteries - Check out FogStar and...
S1E30 . Refitting My Old Sailboat in Crazy Wind | Real DIY Boat Life, Storage Fixes & Splicing Wins
Sailing UV ( UltraViolet )

S1E30 . Refitting My Old Sailboat in Crazy Wind | Real DIY Boat Life, Storage Fixes & Splicing Wins

Refitting this old sailboat feels a little like therapy… if therapy involved heat waves, glue guns from the 90s, and a boat heeling like it wants to buck me off. Today I’m tackling more interior fixes: templating new shelves, building out bathroom storage, dealing with rogue cabinet doors, and addin...
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...
This Is Why Sailing Costs Less Than Rent (Seriously)  – Ep 356 Lady K Sailing
Lady K Sailing

This Is Why Sailing Costs Less Than Rent (Seriously) – Ep 356 Lady K Sailing

Think sailing is only for millionaires? Think again. In this episode, we break down the real costs of living aboard and show how affordable it can be to start sailing. From budget boats to smart marina hacks, you’ll see exactly how people are doing it — right now. #Sailing #SailboatLife #LadyKSailin...
First Time Up the ICW! | Big Comfort Upgrades on Escapade! Ep-195
Leading the Escapade

First Time Up the ICW! | Big Comfort Upgrades on Escapade! Ep-195

We’re heading up the ICW for the very first time! 🚤 From Stuart to Fort Pierce, it’s a whole new kind of adventure for us aboard Escapade. Along the way, we’re showing off a few small upgrades that are making a huge difference — including our new electric table leg that transforms our salon into a c...
S1E29 . DIY Boat Life: Sweat, Sawdust, and a Few Regrets.
Sailing UV ( UltraViolet )

S1E29 . DIY Boat Life: Sweat, Sawdust, and a Few Regrets.

It started simple — just mount the tender, test the davits, and clean up a few things. Fast forward to midnight, and I’m covered in sawdust, sweating through my shirt, and wondering what went wrong 😅 This is real DIY boat life — no scripts, no sponsors, just hard work and questionable decisions on ...
When Your Wife Won’t Go Sailing – How to Get Your Partner Onboard the Dream – 355 -Lady K Sailing
Lady K Sailing

When Your Wife Won’t Go Sailing – How to Get Your Partner Onboard the Dream – 355 -Lady K Sailing

So you’ve worked your whole life, ready to retire and sail off into the sunset — but your spouse just isn’t interested in sailing. You’re not alone. In this episode of Lady K Sailing, we talk about why one partner often resists the sailing lifestyle and how you can bridge that gap using real data, e...
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...
Installing a MARINE AIR CONDITIONER From ALIBABA…GAME CHANGER or a BIG MISTAKE?! Ep 193
Leading the Escapade

Installing a MARINE AIR CONDITIONER From ALIBABA…GAME CHANGER or a BIG MISTAKE?! Ep 193

Jase is back in the US, which means it’s upgrade time! After months of waiting, we can finally dive into all the projects we’ve been holding off on — because let’s be honest, there’s no better place for Amazon boxes and endless options than America. This week, Jase tackles a full list of long-awaite...
Sailing Is Way Scarier Than You Think – Ep 353 – Lady K Sailing
Lady K Sailing

Sailing Is Way Scarier Than You Think – Ep 353 – Lady K Sailing

Sailing looks calm, romantic, and free — until it isn’t. In this video, we explore the real-life disasters and accidents that show just how fast things can go wrong at sea — from the 1979 Fastnet Race tragedy to the Cheeki Rafiki and Sydney to Hobart storm, to modern-day survival stories that remind...
Countdown to Splash Day 💦 Nearing the End of our 40ft Sailboat Restoration
Chesca & Ben

Countdown to Splash Day 💦 Nearing the End of our 40ft Sailboat Restoration

In this weeks video we crack on with getting everything ready in preparation for Flying Freedom to return to the water after 4 years on land. Painting, instruments, guard netting, it all gets done. Well, nearly. 🚢 Join Our Crew on Patreon Want to support our sailing adventure and get exclusive behi...
Valiant 40 Sailboat | The Legendary Bluewater Cruiser Changed Offshore Sailing Ep 352 Lady K Sailing
Lady K Sailing

Valiant 40 Sailboat | The Legendary Bluewater Cruiser Changed Offshore Sailing Ep 352 Lady K Sailing

The Valiant 40 sailboat is one of the most iconic offshore cruisers ever built. Designed by Bob Perry in the 1970s, this legendary 40-foot yacht combined speed, comfort, and safety in a way no production cruiser had before. In this video, we take a deep dive into the history, design, performance, a...
S1E26. Fixing Leaks, Helm Station Mods & Aft Cabin Refit | Sailing UV.
Sailing UV ( UltraViolet )

S1E26. Fixing Leaks, Helm Station Mods & Aft Cabin Refit | Sailing UV.

Welcome back aboard Sailing UV! In this week’s episode, we tackle a creative rebuild of the helm station sole, work on sealing up the aft cabin, and hunt down leaks that have been haunting the engine room. Along the way, we give the windlass some much-needed love, talk through project challenges, an...
Do NOT Buy – Prout 34 Bluewater Catamaran – Ep 351 – Lady K Sailing
Lady K Sailing

Do NOT Buy – Prout 34 Bluewater Catamaran – Ep 351 – Lady K Sailing

Looking for a proven bluewater catamaran that won’t break the bank? Meet the Prout 34 Catamaran, a legendary British cruising multihull designed for serious passagemaking. In this video, we take a closer look at the history, design, layout, and sailing performance of the Prout 34—one of the smallest...
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