Watch Sailing & Boating Adventures Around the World – Page 4 of 59

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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I’m the Captain Now — Are We Still Sailing Together? | Ep. 164
Sailing SV CUBA

I’m the Captain Now — Are We Still Sailing Together? | Ep. 164

Hurricane season is over and we are finally back to sailing again! A lot of unexpected things happened while we were working on our boat below the hurricane belt. In this episode, I am turning from crew to captain and we sail to a different country, just to get our mail 🫣 But even the small things...
Al is flying solo and exploring Poros! (Sailing Dakini – Leave to Roam Ep. 72)
Leave to Roam

Al is flying solo and exploring Poros! (Sailing Dakini – Leave to Roam Ep. 72)

That's right! I am flying solo while Kel is in Eastern Europe with her parents. Unfortunately it doesn't start well , after sailing in the rain our VHF aerial falls of. It's really mixed weather in Poros when I arrive but it doesn't ruin the big catamaran boatshow. Then I sail, ...
Wave Rover is Back \ Crossing the North Atlantic on the Queen Mary 2 in November
Sailing Wave Rover

Wave Rover is Back \ Crossing the North Atlantic on the Queen Mary 2 in November

In this video, my wife (Mrs Rover) and I enjoy crossing the North Atlantic in style onboard the Queen Mary 2 from South Hampton to New York. "Forge Your Own Adventure" [UPDATED BUILDING PLANS FOR WAVE ROVER 2] [ SUPPORT MY VIDEOS - PATREON ] Head over to my Patreon Page where you can ...
Episode 7: Harder than I Thought: Sailing Alone on the Pacific after Divorce
Calico Skies Sailing – New Horizons

Episode 7: Harder than I Thought: Sailing Alone on the Pacific after Divorce

This is my new channel where I will continue the story aboard Calico Skies, but with a fresh perspective, new adventures, and the same passion for sailing, discovery, and storytelling that has always been at the heart of my journey. Please Subscribe and continue with the journey of Calico Skies! Ov...
Fuel Lines vs. Me
Sailing With Phoenix | Oliver

Fuel Lines vs. Me

Feeling absolutely wrecked but refusing to slow down, I dive headfirst into a full day of fuel lines, filters, smoking engines, wrong-size hoses, and total chaos. 00:00 – Feeling Sick, Still Working 02:12 – Smoke Check & First Issues 05:47 – Replacing Fuel Hoses 09:27 – Fighting the Filters 14:...
Boat Work Begins
Sailing With Phoenix | Oliver

Boat Work Begins

We’re officially back in refit mode. It’s going to be five solid months of boat work from here on out. Hope you’re ready. In this episode: 00:00 – The Great Hose Saga 06:30 – Battery System Problems 10:00 – Plans for the Day 14:00 – Jib + Staysail Fixes 22:00 – Line Bags & Engine Compartment Ch...
Leaving Phoenix + New Boat Tour
Sailing With Phoenix | Oliver

Leaving Phoenix + New Boat Tour

Saying goodbye to the boat that saved my life and starting a whole new chapter on a new vessel. It’s emotional, messy, and exciting all at once… here’s to new beginnings and keeping the dream alive. ⛵️ New Boat Details: Model: Pacific Seacraft 40 Year: 1998 Length overall (LOA): ~ 42′ 2″ Waterline ...
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...
My Final Sail Aboard Phoenix (and Losing the Drone)
Sailing With Phoenix | Oliver

My Final Sail Aboard Phoenix (and Losing the Drone)

Well, my last voyage with her was bound to happen eventually. I’m glad we ended things on such a high note. The sailing conditions were perfect, magical, even (aside from losing the drone 😅). The Molokai sea cliffs at sunset were absolutely breathtaking, and she brought us home safely one last time....
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...
A Sporty 350 Mile Sail from Kona to Hilo 🌊
Sailing With Phoenix | Oliver

A Sporty 350 Mile Sail from Kona to Hilo 🌊

We battle big waves, broken gear, and beating to windward while sailing from Kona to Hilo on Hawaii's Big Island. This one was a doozy for sure. I also chat a bit about buying the new boat. More details on this very soon. And as always thank you for watching! ⛵ Join the Crew + Follow Along: 🌐...
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...
SOLO SAILING THE BRAZIL COAST
The Cruising Kiwis

SOLO SAILING THE BRAZIL COAST

SOLO SAILING THE BRAZIL COAST Welcome back aboard our floating home. After an unforgettable family reunion in Lucerne, Switzerland, where Finn and and Ben brought home silver for New Zealand at the rowing World Cup, Rob returns to Brazil for a solo sailing mission aboard our boat in the stunning m...
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...
Sailing 220 Miles From Oahu to the Big Island
Sailing With Phoenix | Oliver

Sailing 220 Miles From Oahu to the Big Island

A 220-mile sail from Oahu to the Big Island became a lesson in patience and respect. Between calm seas and sudden squalls, we were forced to change course — the sea had other plans. ⛵ Join the Crew + Follow Along: 🌐 All My Links 📍 Live Tracker – Where’s Phoenix Now? 👕 Official Merch 📸 Instag...
I Tried Sneaking Onto Hawaii’s Most Epic Sailing Canoe Race
Sailing With Phoenix | Oliver

I Tried Sneaking Onto Hawaii’s Most Epic Sailing Canoe Race

Huge thanks to the Hawaiian Sailing Canoe Association for inviting me out to watch this incredible race 🙌 Learn more: | ⛵ Join the Crew + Follow Along: 🌐 All My Links 📍 Live Tracker – Where’s Phoenix Now? 👕 Official Merch 📸 Instagram 🎵 TikTok 📘 Facebook #hawaii #hawaiiansailing #ca...
HOW WE SAIL (shorthanded) around the world! [RED SEAS]
Sailing Red Seas

HOW WE SAIL (shorthanded) around the world! [RED SEAS]

READ our article about short handed sailing here: www.red-seas.com/shorthanded SUPPORT our journey: www.patreon.com/redseas SUBSCRIBE to our channel: www.youtube.com/redseas ⛵ 350 Miles of Open Ocean | Sailing from Niue to Samoa 🌋 Two sailors. One 47ft catamaran. 350 miles of empty Pacific Ocean. ...
Sailing 4 Countries in One Week + Special Announcement  E.150 – SV CUBA
Sailing SV CUBA

Sailing 4 Countries in One Week + Special Announcement E.150 – SV CUBA

We lift the anchor, we sail and repeat. This has been our sailing journey around the world for the last 5 years. Join us this week as we sail to four countries in one week and have a very special announcement! *Want to support our journey so we can keep sharing the adventure? Patreon: Buy Salsa a ...
Everyone Talks About This Sandbar…
Sailing With Phoenix | Oliver

Everyone Talks About This Sandbar…

We’re anchored in Kāneʻohe Bay, Oʻahu, and after a rough start—including running aground on a reef (watch that episode here: finally make it to the iconic sandbar, where turquoise water, sea turtles, coral, and even a possible puffer fish await. Later, we hike up Chinaman’s Hat (Mokoliʻi) and wrap ...
Tandem Kiteboarding Adventures —– (Day 42/100 Water World Challenge)
Adventureman Dan

Tandem Kiteboarding Adventures —– (Day 42/100 Water World Challenge)

Kiteboarding at my new and MOST favorite anchorage in the entire Bahamas..... What FUN! :) Also, check out these adventures on Nicole's channel: www.youtube.com/@SailingArtha _____________________________________________________________________________ 🤜🏼Exclusive/early access & Help suppo...
NEW Anchorage = NEW Home!!! —– (Day 41/100 Water World Challenge)
Adventureman Dan

NEW Anchorage = NEW Home!!! —– (Day 41/100 Water World Challenge)

Moving my anchor means, moving my home! This is what I LOVE, 1hr of work, and a whole new view! Also, check out these adventures on Nicole's channel: www.youtube.com/@SailingArtha _____________________________________________________________________________ 🤜🏼Exclusive/early access & Help ...
Sailing To *Remote* Ragged Island Bahamas —– (Day 40/100 Water World Challenge)
Adventureman Dan

Sailing To *Remote* Ragged Island Bahamas —– (Day 40/100 Water World Challenge)

Waking up on the open ocean, Also, check out these adventures on Nicole's channel: www.youtube.com/@SailingArtha _____________________________________________________________________________ 🤜🏼Exclusive/early access & Help support my adventures: Business Inquires: adventuremandanbusines...
Girls Most Private Confessions Under Sail 😳 It’s a Balancing Act! Ep.147
Sailing SV CUBA

Girls Most Private Confessions Under Sail 😳 It’s a Balancing Act! Ep.147

You won’t believe what the Girls admits while under sail 😳 No bathroom, no breaks—just real boat life struggles. Don’t miss this unfiltered moment at sea!
2 Solo Sailors 150nm Island HOP! (Day 39/100 Water World Challenge)
Adventureman Dan

2 Solo Sailors 150nm Island HOP! (Day 39/100 Water World Challenge)

Nicole on Artha a 1978 28' Bristol Channel Cutter. And myself on a 1984 Beneteau Idylle 38'. Together we solo set sail from one Bahamas Island to another. AND on New Years day no less! What a fun way to kick off the new year! Also, be sure to check out these adventures on Nicole's ch...
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