Watch Sailing & Boating Adventures Around the World – Page 2 of 27

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 25-48 of 627 results
Meeting Mana In Casamance Senegal | How I Immersed Myself Into The Land I Sailed To | S7 Epsd 24
Winded Voyage Sailing

Meeting Mana In Casamance Senegal | How I Immersed Myself Into The Land I Sailed To | S7 Epsd 24

Sailing is not just about the journey, but the destination. And once there, it’s about spending time there and meeting people. That’s the real way to know a place. I’ve met Mohamed who shows us the house he’s building and he introduces me to Mana. I’m welcomed like a relative or close friend. Mana s...
Weathering The Ages | My Sailing Tips & Challenges For Perpetual Youth & Longevity | S7 Epsd 22
Winded Voyage Sailing

Weathering The Ages | My Sailing Tips & Challenges For Perpetual Youth & Longevity | S7 Epsd 22

Forget what you thought you knew about aging gracefully. I’m not just an old sea dog, I’m reinventing vitality, one wave, one encounter at a time. My secret weapon? Solo sailing. From battling the elements to blending into foreign cultures. Discover how the ceaseless demands of the open ocean are ke...
Transported Into Senegal’s Sacred Rhythms Beautiful Faces & Mystic Dancers of Casamance | S7 Epsd 21
Winded Voyage Sailing

Transported Into Senegal’s Sacred Rhythms Beautiful Faces & Mystic Dancers of Casamance | S7 Epsd 21

What if everything you thought you knew about Senegalese football was just the surface? I was taken beyond the tourist trails of Senegal, by my guide and friend Mohamed. To a soccer game between a young aggressive rookie team and the old experienced veterans. Join me as I share my unbelievable journ...
Mohamed M’invite A Un Marriage | Un Réve De Vivre Une Vraie Experience Sénénegalaise | S7 Epsd 20
Winded Voyage Sailing

Mohamed M’invite A Un Marriage | Un Réve De Vivre Une Vraie Experience Sénénegalaise | S7 Epsd 20

Mes véritables aventures africaines commencent maintenant. Avec mon nouvel ami Mohamed, rencontré lors d'un déjeuner. Tel un dauphin me guidant jusqu'ici, une force supérieure m'a mis en contact avec lui. Il a été un véritable trésor. Je l'ai surnommé « Mon Prophète Mohamed ». Ce...
Meeting Mohamed | He Made My African Dream Come True | To Feel The Real Senegal | S7 Epsd 20
Winded Voyage Sailing

Meeting Mohamed | He Made My African Dream Come True | To Feel The Real Senegal | S7 Epsd 20

I believe I have found one of the best city anchorages ever here in the city of Ziguinchor on the River Casamance in Senegal. At the local restaurant nearby, I regularly go to, I meet Mohamed over lunch. He would change my life here. Thanks to him, we immerse ourselves in the vibrant chaos of a Sene...
Casamance River Reflections | Unexpected Serenity Of The River & Anchored In Ziguinchor | S7 Epsd 19
Winded Voyage Sailing

Casamance River Reflections | Unexpected Serenity Of The River & Anchored In Ziguinchor | S7 Epsd 19

Navigating the tranquil Casamance River, we discover the profound peace of life aboard Galopin, embracing the river’s rhythm as a counterpoint to the ocean’s fury. It’s an intimate exploration of tranquility and unexpected beauty, where the challenges of living anchored on the river along the gentle...
Ocean Swells, Fishermen & Into The River’s Mouth | A Dolphin Guided African River Ascent | S7 Epsd18
Winded Voyage Sailing

Ocean Swells, Fishermen & Into The River’s Mouth | A Dolphin Guided African River Ascent | S7 Epsd18

Imagine leaving the vast, ferocious ocean behind, after dealing with torn sails, broken autopilot and dodging local fishermen all night long. To then enter a major river with sand banks and unseen currents. This is what happens when Galopin, my sailing vessel designed for the open sea dares to chall...
Ocean Survival Instincts | How Me & My Boat Weathered The Atlantic’s Unrelenting Fury | S7 Epsd 17
Winded Voyage Sailing

Ocean Survival Instincts | How Me & My Boat Weathered The Atlantic’s Unrelenting Fury | S7 Epsd 17

What would you do when the unforgiving Atlantic throws its absolute worst at you? The autopilot decides to break down and fixing it pushes the body to its limits? When your vessel is being battered and every instinct screams panic but must manage to improvise and make split-second choices that keep ...
Nature’s Fury Unleashed & How I Go From Disaster To Recovery Aboard Galopin | S7 Epsd 15
Winded Voyage Sailing

Nature’s Fury Unleashed & How I Go From Disaster To Recovery Aboard Galopin | S7 Epsd 15

My resilience was being severely tested here in Tarrafal do Santiago. It was Mother Nature's turn to come down hard on the town and me. Intense rain fell non-stop for hours. I took it as a good sign. It washed the boat and I filled up with fresh rain water. That was all that was good. More bad ...
I’m Cursed Here | Things Continue To Fail Since Being Stuck In Tarrafal Do Cabo Verde | S7 Epsd 14
Winded Voyage Sailing

I’m Cursed Here | Things Continue To Fail Since Being Stuck In Tarrafal Do Cabo Verde | S7 Epsd 14

If there is one skill thing to learn being a full time sailor, it is patience. We are always waiting for, the weather, a part or in my case here, to go to court. And at this anchorage is really testing my patience. I clean up after the police search and can't find certain things. The swell and ...
Innocent Yet Guilty | Free To Go Until Later Court Date In Tarrafal Do Cabo Verde | S7 Epsd 14
Winded Voyage Sailing

Innocent Yet Guilty | Free To Go Until Later Court Date In Tarrafal Do Cabo Verde | S7 Epsd 14

In the previous episode I was taken into custody and taken to the police station. After being questioned, the contents of my bag were itemized by the police as seizure. In those contents were two small bags of weed. That was enough for the police to hold me in custody in the local jail. It wasn'...
Arrested Jailed & Searched For Drugs | Welcome To Tarrafal Do Santiago Cabo Verde | S7 Epsd 13
Winded Voyage Sailing

Arrested Jailed & Searched For Drugs | Welcome To Tarrafal Do Santiago Cabo Verde | S7 Epsd 13

Sailor Alex recounts his experience of being arrested in Tarrafal de Santiago, Cabo Verde, under circumstances he claim were misunderstood. Three months prior, they traveled from Tarrafal Cabo Verde to Dakar Senegal intending to repair his boat engine. After completing repairs, Alex had to leave Sen...
Sailing Into Cape Verdean Waters | The West African Atlantic | Senegal To Cabo Verde | S7 Epsd 11
Winded Voyage Sailing

Sailing Into Cape Verdean Waters | The West African Atlantic | Senegal To Cabo Verde | S7 Epsd 11

We're under way on our passage from Dakar to Cabo Verde. Nearing the archipelago, I could see the difference in the ocean. This was Cape Verdean conditions. I’m all too familiar with them. My hopes were to get in and anchor before dark. We were not very fast the first couple of days. I could fe...
Big Test For Engine & Crew | A Severe Jelly Sting | Sailing Dakar To Cabo Verde Africa | S7 Epsd 10
Winded Voyage Sailing

Big Test For Engine & Crew | A Severe Jelly Sting | Sailing Dakar To Cabo Verde Africa | S7 Epsd 10

Just hours away from sailing from Dakar, Senegal to Cabo Verde. We just need a engine starter, ignition, alternator and diesel engine philosophy. We board the crew starting with Asahi, the Japanese cycle traveler who's cycling around Africa. As well as Paul and Gauthier from France who scrape t...
Why I’m Sailing Solo Nonstop Around the World
Sailing With Phoenix | Oliver

Why I’m Sailing Solo Nonstop Around the World

I’ve bought a new boat and I’m getting ready to sail solo, non-stop, around the world. It’s without a doubt the hardest thing I’ve ever set out to do, but maybe the most meaningful. In this video, I try to unpack why I’m taking on something this extreme and what’s really driving the decision. Curiou...
Rebuilding My Perkins Diesel Engine In Africa | Simone The Engine Comes Home | S7 Epsd 9
Winded Voyage Sailing

Rebuilding My Perkins Diesel Engine In Africa | Simone The Engine Comes Home | S7 Epsd 9

Arona and crew brought Simone the Perkins Diesel engine back home to Galopin via the beach and dinghy. He installed it just enough for us to go a give it a feel. Simone purred and we gloated. One of two of his most memorable jobs of his career. That’s the good news. Im having trouble with my solar V...
I Finally Sailed to Maui — Where It All Began
Sailing With Phoenix | Oliver

I Finally Sailed to Maui — Where It All Began

We set sail from Hilo to Maui with light winds 90% of the way, finally catching a chill downwind run. I reflect a little bit on why I love sailing so much and how the hard work does eventually pay off. After arriving in Lāhainā we battle surf breaks to get the dinghy ashore and then hike a wild loca...
Diesel Wears A Blue Dress | Rebuilding Simone My Perkins Diesel Engine In Senegal Africa | S7 Epsd 8
Winded Voyage Sailing

Diesel Wears A Blue Dress | Rebuilding Simone My Perkins Diesel Engine In Senegal Africa | S7 Epsd 8

We are into cosmetics now. Simone the Perkins diesel engine is tuned and ready for it’s beauty treatment. She will proudly wear the Perkins brand blue. Meanwhile I non/slip my floor, make friends with a jumping spider and watch a boat launch enviously. All the while Arona is fixing he electrical sys...
Sailing Solo to Escape a Hurricane | Bahamas 🇧🇸 to the US 🇺🇸 EP-192
Leading the Escapade

Sailing Solo to Escape a Hurricane | Bahamas 🇧🇸 to the US 🇺🇸 EP-192

With Hurricane Erin rapidly intensifying to a Category 5, Jase finds himself completely alone on Escapade in the Bahamas. While I’m back in Australia, exploring what Tasmania and catching up with family & friends, he’s forced to make a tough call — set sail solo or risk getting caught in the pat...
My One Eyed Driver & Simone’s Magician Mechanic | Rebuilding My Diesel Engine In Africa | S7 Epsd 7
Winded Voyage Sailing

My One Eyed Driver & Simone’s Magician Mechanic | Rebuilding My Diesel Engine In Africa | S7 Epsd 7

Doing a full diesel engine rebuild takes time, and money. Arona is diligently caring for Simone the Perkins 4108. As I take care of projects on Galopin while waiting. Sometimes I need to get out of the CVD club and get stuff like groceries and cash. And that's where Tafa, my one eyed driver com...
The Greatest Mechanic I Know Makes Simone Roar Again | Rebuilding My Diesel Engine Africa | S7 Epsd6
Winded Voyage Sailing

The Greatest Mechanic I Know Makes Simone Roar Again | Rebuilding My Diesel Engine Africa | S7 Epsd6

The greatest diesel mechanic I have known throughout my travels is Arona. Here at the Dakar Yacht Club or CVD. He's been caring for my dear Simone, the Perkins 4108 for many years. Now Simone is on his bench and ready to roar back to life again. 00:00 Intro 00:36 Head care 01:16 Love that dirt...
She Left Me… and Now There’s a Hurricane Coming!! Ep-191
Leading the Escapade

She Left Me… and Now There’s a Hurricane Coming!! Ep-191

Go to and use code ESCAPADE to get 5% off your Holafly eSIM for your next trip! After 2.5 years onboard, Janaye has flown back to Australia for some much-needed time with family, friends, and the little luxuries of land life — hot showers, delicious food, and even driving a car again! 🇦🇺✨ But whi...
Greatest Shade Tree Mechanic I Know Rebuilding My Diesel Engine | This Is Sailing Africa | S7 Epsd 5
Winded Voyage Sailing

Greatest Shade Tree Mechanic I Know Rebuilding My Diesel Engine | This Is Sailing Africa | S7 Epsd 5

My boat Galopin and I are waiting for Simone, our Perkins diesel engine to have her full makeover by Arona, greatest shade tree mechanic I know. We’re living here during Senegal’s rain season. Which offers the most surreal views and bitch slapping storms. And through all the wet and dry weather we g...
Sinister Boat Gets Too Close | & Best Machinist Does My Engine | This Is Sailing Africa | S7 Epsd 4
Winded Voyage Sailing

Sinister Boat Gets Too Close | & Best Machinist Does My Engine | This Is Sailing Africa | S7 Epsd 4

After a brutal storm, a strange empty traditional boat has drifted very close to me and my boat. I later learn the boat has a sinister story. The storm has wrecked several boats on the beach, and I go to assess the damage. Arona is back and working on my engine. We take it to the best machinist in D...
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