Watch Sailing & Boating Adventures Around the World

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 1-17 of 17 results
First Sail Alone Since Sailing To Hawai’i
Sailing With Phoenix | Oliver

First Sail Alone Since Sailing To Hawai’i

In October 2026 I will attempt a 30,000 mile solo nonstop circumnavigation of the planet aboard my Pacific Seacraft 40, "Phoenix do Mar", meaning Phoenix of the Sea in Portuguese. Departing from Port Townsend, Washington, this voyage will cross the world’s most remote oceans in one continu...
64 Days Until I Sail Nonstop Around The World
Sailing With Phoenix | Oliver

64 Days Until I Sail Nonstop Around The World

Jerome and my brother join me on the first phase of sea trials ahead of my circumnavigation. In October 2026 I will attempt a 30,000 mile solo nonstop circumnavigation of the planet aboard my Pacific Seacraft 40, "Phoenix do Mar", meaning Phoenix of the Sea in Portuguese. Departing from P...
I’ve been doing a bad job…
Sailing With Phoenix | Oliver

I’ve been doing a bad job…

The boat finally goes back in the water after months of being on the hard. I also talk about why I haven't been uploading content recently and where things stand as I get closer to finishing the refit. We’re getting there. Slowly but surely. And huge thanks to Taylor for the drone footage - ...
Impeller, Engine Smoke, and Winches
Sailing With Phoenix | Oliver

Impeller, Engine Smoke, and Winches

I replace an engine impeller, overthink oil levels, and accidentally become a watchmaker. Nothing's exploded (yet), lessons are learned (maybe), and seven more winches still loom. ⛵ Join the Crew + Follow Along: 🌐 All My Links 📍 Live Tracker – Where’s Phoenix Now? 👕 Official Merch 📸 Ins...
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...
We Broke Down in the Middle of Nowhere on Hawaii’s Big Island
Sailing With Phoenix | Oliver

We Broke Down in the Middle of Nowhere on Hawaii’s Big Island

Nothing ever goes to plan, but that's half the fun. What began as a laid-back drive to the volcano quickly turned into an off-road adventure through lava fields, green sand, and a broken-down Jeep miles from anywhere. ⛵ Join the Crew + Follow Along: 🌐 All My Links 📍 Live Tracker – Where’s P...
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...
Fixing the Engine Before Sailing to Hawaii’s Big Island
Sailing With Phoenix | Oliver

Fixing the Engine Before Sailing to Hawaii’s Big Island

I’m preparing to sail to the Big Island — but first, my diesel engine throws me a curveball with a leaking raw water pump. ⛵ Join the Crew + Follow Along: 🌐 All My Links 📍 Live Tracker – Where’s Phoenix Now? 👕 Official Merch 📸 Instagram 🎵 TikTok 📘 Facebook #BoatMaintenance #SailboatLif...
Scuba Diving at Electric Beach Oahu 🐠
Sailing With Phoenix | Oliver

Scuba Diving at Electric Beach Oahu 🐠

I'm back in the water at Electric Beach, O‘ahu, one of Hawaii’s most stunning dive spots! 🌊🏝️ This time I’m joining Sam and Jamie for more scuba training… and we found a lot more than just an anchor! 🐢 Follow Sam & Jamie for more amazing dive adventures: 👉 Jamie Underwater Photography: 👉...
Sailing 40 Hours Back to Oahu From Kauai ⛵
Sailing With Phoenix | Oliver

Sailing 40 Hours Back to Oahu From Kauai ⛵

All good things must come to and end... After two weeks on Kauai, it’s time to sail back to Oahu. Join Phoenix, Rhoads, and me on a 40-hour passage across the Kaʻieʻie Waho Channel. ⛵ Join the Crew + Follow Along: 🌐 All My Links 📍 Live Tracker – Where’s Phoenix Now? 👕 Official Merch 📸 Instag...
A SENSATIONAL Trailerable Pocket Cruiser: The Com-Pac 17 Sun Cat for $9,500! [[SOLD 9/16/25]]
BoatFools Sailing

A SENSATIONAL Trailerable Pocket Cruiser: The Com-Pac 17 Sun Cat for $9,500! [[SOLD 9/16/25]]

#boatfoolssailing #sailingboat #pocketcruiser #trailersailer [[SOLD 09/16/2025]] A SENSATIONAL Trailerable Pocket Cruiser: A Com-Pac 17 Sun Cat for $9,500! TOC: 00:00 What did we just find?!? 00:24 Intro to the Comp-Pac 17 Sun Cat - And "Kenadian" 01:02 Walk around the boat and a look a...
My First Time Scuba Diving 🤿
Sailing With Phoenix | Oliver

My First Time Scuba Diving 🤿

I finally went scuba diving for the first time off the coast of Kauai, Hawaii! Big thanks to Sam and Jamie for guiding me on this dive! Be sure to check them out and follow their adventures here: 👉 Jamie Underwater Photography: 👉 Sam Beane Diver: ⚓ If you enjoy this journey, don’t forget to like...
Sailing From O’ahu to Kauai
Sailing With Phoenix | Oliver

Sailing From O’ahu to Kauai

We set sail from Oahu to Kauai expecting a 25-hour downwind passage… but halfway across, the unexpected happened: a tsunami warning was issued for all of Hawaii following an 8.7 earthquake in Russia. With Kauai in sight, we suddenly had to turn back out to sea as the Coast Guard ordered all vessels...
Installing Windlass Foot Switches — Sort Of
Sailing With Phoenix | Oliver

Installing Windlass Foot Switches — Sort Of

Today’s episode is all about cursed boat projects. I’m back in Waikiki and tackling a foot switch install for my broken windlass remote. Along the way, I get hot, frustrated, sentimental, and somehow wired things backwards, but hey, it still works (sort of). This is real-life boat work: messy, slow...
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 ...
I Ran Aground Sailing to Kāneʻohe Bay Sandbar – Hard Lessons Learned
Sailing With Phoenix | Oliver

I Ran Aground Sailing to Kāneʻohe Bay Sandbar – Hard Lessons Learned

Hello hello! Sailing adventures resume as my brother joins me in Hawai’i. We set sail from Waikiki Yacht Club into 30+ knot headwinds, bound for the stunning sandbar in Kāne‘ohe Bay, Oʻahu. What should have been a scenic day sail quickly turned stressful: wind advisories, towing mistakes, and hitti...
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