Watch Sailing & Boating Adventures Around the World – Page 20 of 222

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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Is this Hidden Gem of a Greek Island My Favorite? | Skyros
Dylan Magaster

Is this Hidden Gem of a Greek Island My Favorite? | Skyros

🔥 Support the journey and get the salve I use daily in the sun, sea, and wind: We set off to explore one of the most underrated Greek islands — Skyros. What started as a peaceful scooter ride quickly turned into a breakdown saga, hidden beaches, ancient ruins, mysterious cats, and wild island horse...
Getting Food & Water in Remote Borneo, Battling the Engine and Trying to Repair the Broken Autopilot
Sailing Triteia

Getting Food & Water in Remote Borneo, Battling the Engine and Trying to Repair the Broken Autopilot

Episode 435 : Hello Friends, On this episode I stock up on Food, Water and Fuel in the town of Kumai in Borneo and battled the engine to get it started. I then head down river to wait for a weather window to sail to Belitung. While I am waiting I get into trying to make two broken Autopilots on...
One Week In… Total Rudder Failure on Our 40ft Sailboat
Chesca & Ben

One Week In… Total Rudder Failure on Our 40ft Sailboat

One week into working on our sailboat and we’ve already hit a major setback… our rudder has completely failed and ceased. What started as routine maintenance to drop the rudder and inspect quickly turned into a disaster when we discovered the rudder fused into the bearing and housing that means a fu...
S3, Ep34 Infinite Possibilities on Catalina Island
Sailing Into the Mystic

S3, Ep34 Infinite Possibilities on Catalina Island

Do you want to see what Catalina Island has to offer? Join us in Episode 34 as we share our discoveries and continue to push our sailing skills to get ready to live aboard and sail south in retirement. This is part three of our three episode series of our sailing trip to Catalina Island. Catalina I...
Guess what Cory did during our Final Days onboard [E344]
Wildly Intrepid Sailing

Guess what Cory did during our Final Days onboard [E344]

We wanted to sail North to the Chesapeake Bay but changed our mind. Hurricane Season has started so it's time to pack up the boat, enjoy a few last days on the water with its thunderstorms and go find shelter. Plus after over 15 years Cory did something crazy. Oh and you wouldn't believe h...
Hidden Dangers – Not What You’d Expect | S4 E26
Sailing with six

Hidden Dangers – Not What You’d Expect | S4 E26

From above, this anchorage looked like pure paradise — turquoise water, lush green shores, glassy waves. But not all dangers are on the horizon. Some are hidden… and not what you’d expect. In this episode, we repair a snapped surfboard with whatever we can find, head ashore for provisions, explore ...
BLUE MARLIN SHADOWED US ON 1800 MILE ATLANTIC CROSSING TO BRAZIL
The Cruising Kiwis

BLUE MARLIN SHADOWED US ON 1800 MILE ATLANTIC CROSSING TO BRAZIL

BLUE MARLIN SHADOWED US ON 1800 MILE ATLANTIC CROSSING TO BRAZIL From one of the worlds most remote inhabited islands to the endless blue of the South Atlantic, this episode takes you from or final adventures on St Helena to the start of our 3000 mile blue water passage to Brazil. With just days le...
OFF GRID LIFE: CLEAN FUEL & COLD AIR ON OUR ALUMINIUM CATAMARAN
Sailing Dawn Hunters

OFF GRID LIFE: CLEAN FUEL & COLD AIR ON OUR ALUMINIUM CATAMARAN

Living Off-Grid Dawn Hunters Style on sailing catamaran! 📺 THIS IS DAWN HUNTERS SEASON #4 EPISODE 15 ➡️ S4E15 ⛵WANT TO KEEP VIDEOS COMING? SUPPORT OUR PRODUCTION HERE: If you’d like to help with this production please consider supporting us on Patreon. (SUPPORT TIERS GO AS LOW AS $5 PER MONTHS)...
Navigating LEAKS + SQUALLS Sailing New Zealand to Australia
Harbors Unknown

Navigating LEAKS + SQUALLS Sailing New Zealand to Australia

​​Subscribing to the channel is FREE, ensures you never miss a video and really helps us out! If you enjoy the episode give it a thumbs up and drop us a comment down below! Navigating LEAKS + SQUALLS Sailing New Zealand to Australia Sailing from New Zealand to Australia across the Tasman Sea is ne...
Sailing Into a Storm | Greek Island Adventure to Skyros
Dylan Magaster

Sailing Into a Storm | Greek Island Adventure to Skyros

🌊 Support the Journey: We set sail from a quiet bay on the island of Proso, heading toward Skyros — a place of tiny horses, lobsters, and ancient legend. What began as a calm journey quickly turned into a tense wait-out as a lightning-laden storm rolled in. On a sailboat, thunderstorms aren’t just...
I’m A Freaking Genius | How I solve Problems On My Boat | Island Sailing In Cabo Verde | S6 Epsd 128
Winded Voyage Sailing

I’m A Freaking Genius | How I solve Problems On My Boat | Island Sailing In Cabo Verde | S6 Epsd 128

Things seem to go wrong at the wrong time. And that's when you have to find a solution. Because there are no problems, only solutions. I manage to steer Galopin without the autopilot. Later I fix the problem without the proper parts. Pay tribute to Wendy, who is leaving us, and head East to Da...
Taking a Speed Boat into the Jungles of Borneo To See Wild Orangutans, Gibbons and Proboscis Monkeys
Sailing Triteia

Taking a Speed Boat into the Jungles of Borneo To See Wild Orangutans, Gibbons and Proboscis Monkeys

Episode 434 : Cruising Southeast Asia Hello Friends, On this episode I book a Speedboat Tour with local hotel owner Mr. Majid ( ) and we head off up the river deep into the jungle to visit Camp Leakey in the National Park and see the critically endangered Bornean Orangutans, Proboscis Monkeys, Gi...
S3, Ep33 Cove Hopping on Catalina Island
Sailing Into the Mystic

S3, Ep33 Cove Hopping on Catalina Island

Catalina Island is a beautiful island only 1-2 hours across the ocean from Los Angeles and yet so many Southern Californians have never been there. In this episode we explore the entire east coast of Catalina Island and show our adventures along the way. We learn some embarrassing lessons but love...
BOAT LIFE in Florida | Beaches, Repairs &Sail [E343]
Wildly Intrepid Sailing

BOAT LIFE in Florida | Beaches, Repairs &Sail [E343]

While hiding from hurricanes in St. Augustine, Northern Florida we get a few boat projects done like our dead engine water pump. But we still make time for enjoying Vilano beach and celebrating Kai's very first birthday amidst crazy heat. Instead of traveling on the busy ICW we motor sail in ca...
Risk vs Return – When Surfing Remote Waves Gets Real | S4 E25
Sailing with six

Risk vs Return – When Surfing Remote Waves Gets Real | S4 E25

Surfing remote waves is one of the best parts of living on a boat—but it comes with its fair share of calculated risks. This episode, a snapped leg rope sends Dad’s board into the coral rocks, sparking a rescue mission over sharp lava ledges. There are wipeouts, bumps, scrapes, and board repairs… al...
11 DAYS SAILING to the WORLD’S MOST REMOTE INHABITED ISLAND –  EXPLORING ST HELENA
The Cruising Kiwis

11 DAYS SAILING to the WORLD’S MOST REMOTE INHABITED ISLAND – EXPLORING ST HELENA

11 DAYS SAILING TO THE WORLD'S MOST REMOTE INHABITED ISLAND - EXPLORING ST HELENA After the excitement of Henley Royal Regatta, this week we return to our sailing adventures and one of the world's most remote inhabited islands in the world, St Helena. Perched in the middle of the South A...
Wendy’s Last Swim On Boa Vista | & Celebrating 50 years Of Cape Verde’s Independence | S6 Epsd 127
Winded Voyage Sailing

Wendy’s Last Swim On Boa Vista | & Celebrating 50 years Of Cape Verde’s Independence | S6 Epsd 127

Cabo Verde celebrated 50 years of independence this year. And we joined in the celebrations with music, dance and drink. Then we show how we do laundry here as live aboard sailors. And Wend has one last swim in the bay before we sail off. Wendy will soon be leaving Galopin and I. 00:00 Intro 00:32 ...
SAILING Wildly Intrepid TRAILER
Wildly Intrepid Sailing

SAILING Wildly Intrepid TRAILER

Welcome aboard SV Wildly Intrepid, our 43 feet C&C Landfall. We are Cory, Alex, Coral & Kai originally from Quebec, Canada. Since meeting over 15 years ago in Newfoundland, Canada, we have been consumed by an obsession with travel. Living life one semi-retirement at a time then working for a...
No The Officer Wasnt Looking for a Bribe and No It wasn’t Because of My Tattoos; A RESPONSE VIDEO
Sailing Triteia

No The Officer Wasnt Looking for a Bribe and No It wasn’t Because of My Tattoos; A RESPONSE VIDEO

This is a response to my "Immigration Nightmares" Video If you enjoy the channel please "Like" the videos and Subscribe so you don't miss any future episodes. If you find the videos helpful or entertaining and would like to contribute you can become a Patron at: Othe...
Not Being Allowed to Extend My Indonesian Visa & Being Forced to Clear Out Immediately
Sailing Triteia

Not Being Allowed to Extend My Indonesian Visa & Being Forced to Clear Out Immediately

Episode 433 : Hello Friends, On this episode I attempt to extend my visa and find that once again the Indonesian government has changed the rules and the immigration office refuses to extend my visa forcing me to have to clear out of the country early. Indonesia is known as the absolute worst c...
S3, Ep32 We Bit Off More Than We Could Chew
Sailing Into the Mystic

S3, Ep32 We Bit Off More Than We Could Chew

In Episode 32, titled "We Bit off More than We Could Chew," we embark on an exciting adventure to the Channel Islands. Things take a wild turn when rough seas force us to retreat to Catalina Island, where we share our sailing mistakes, lessons learned, and our decision to stay, which lead ...
ABANDONED MONASTERY on an Remote Greek Island | Skantzoura
Dylan Magaster

ABANDONED MONASTERY on an Remote Greek Island | Skantzoura

Support your skin and this channel get a jar of Captain's Salve: We anchored near a forgotten island in the Northern Sporades and discovered an abandoned monastery once inhabited by Byzantine monks… and later, political exiles. What we found inside shocked us — beds still made, shoes untouched...
OFF THE WATER AND INTO THE FIGHT : A RACE THAT CHANGED EVERYTHING
The Cruising Kiwis

OFF THE WATER AND INTO THE FIGHT : A RACE THAT CHANGED EVERYTHING

OFF THE WATER AND INTO THE FIGHT : A RACE THAT CHANGED EVERYTHING This episode is different, but it's one we had to share. It's not about sailing, but it's about boats, and every bit about the spirit of adventure, family and defying the odds. Our eldest son Finn raced at Henley Royal...
First Look at Our New 40ft Sailboat! Full Boat Tour & Walkaround
Chesca & Ben

First Look at Our New 40ft Sailboat! Full Boat Tour & Walkaround

Here she is! – we bought a sailboat! Meet Flying Freedom ⛵️, our new floating home and the start of our biggest adventure yet. In this video, we’ll give you a full first look and tour of our 40ft Freedom 40/40 sailboat, showing you around every corner before we start the work to get her ready for li...
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