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.

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From Living Abroad to an Expedition Sailboat- Three Boats, Two Countries | Ch4 E1 | The Wayward Life
Wayward Life Sailing

From Living Abroad to an Expedition Sailboat- Three Boats, Two Countries | Ch4 E1 | The Wayward Life

We moved to Ireland in hopes of building a new life of adventure, but quickly figured out that wasn't going to work out how we wanted, so we moved back home and bought a sailboat (Ontario 32)... and then a different sailboat that wasn't what we had thought (custom build 45 foot cutter). So...
Our Last Sail on the Blue Peter- Sailing to Cowichan Bay | Chapter 2 Episode 20 | The Wayward Life
Wayward Life Sailing

Our Last Sail on the Blue Peter- Sailing to Cowichan Bay | Chapter 2 Episode 20 | The Wayward Life

We sail the Blue Peter from Deep Bay to Cowichan Bay to her new owner. We also give you the info about why we chose to sell her and what our future plans are. Patreon: Website: Instagram: Facebook: Music in this video: Epidemic Sound
Sailing By Gusts | From 2 to 7 Knots With the Same Wind and Sails | Ch2 E19 | The Wayward Life
Wayward Life Sailing

Sailing By Gusts | From 2 to 7 Knots With the Same Wind and Sails | Ch2 E19 | The Wayward Life

On a very gusty day, we finally get the boat out of the marina for the first time in 2020. I apologize ahead of time for the really annoying wind noise. We just got a new DJI Osmo for blogging purposes and are in the process of figuring out our new sound and camera equipment. Patreon: Website...
Dickinson Diesel Heater Problems in Below Zero Weather on a Sailboat | Ch2 E17 | The Wayward Life
Wayward Life Sailing

Dickinson Diesel Heater Problems in Below Zero Weather on a Sailboat | Ch2 E17 | The Wayward Life

We have heater problems with BOTH our Dickinson diesel heater and our space heater during a below zero spell and show you a bit of our search for a bigger boat. The struggles of liveaboard sailing life in the winter time in Canada... Patreon: Website: Instagram: Facebook: Music in this video...
Sailing to the Sunshine Coast | Chapter 2 Episode 13 | The Wayward Life
Wayward Life Sailing

Sailing to the Sunshine Coast | Chapter 2 Episode 13 | The Wayward Life

We have a beautiful beam reach sail from Vancouver Island to Thormanby Island on the Sunshine Coast where we anchor up, explore Buchaneer Bay, snorkel, and see some fun wildlife! Patreon: Website: Instagram: Facebook: Music in this video: Epidemic Sound
We Moved Onto Our Tiny Home on the Water! | Chapter 2 Episode 10 | The Wayward Life
Wayward Life Sailing

We Moved Onto Our Tiny Home on the Water! | Chapter 2 Episode 10 | The Wayward Life

We finally move aboard our Ontario 32 Sailboat and celebrate with a dinghy adventure to Newcastle Island, and with some fun snorkelling and freediving. Patreon: Website: Instagram: Facebook:
Sailing to Lasqueti Island | Chapter 2 Episode 9 | The Wayward Life
Wayward Life Sailing

Sailing to Lasqueti Island | Chapter 2 Episode 9 | The Wayward Life

We sail to Lasqueti Island, an off-grid island between Vancouver Island and the Sunshine Coast, and we get to snorkel for the first time this year! Patreon: Website: Instagram: Facebook: Music in this video: Your Vibe- Yomoto Faded- Ooyy Sunny Vacation- Rickard Age
Exploring Newcastle Island (Saysutshun) | Chapter 2 Episode 8| The Wayward Life
Wayward Life Sailing

Exploring Newcastle Island (Saysutshun) | Chapter 2 Episode 8| The Wayward Life

For Michelle’s 30th birthday, we decided to head to Newcastle Island and Protection Island (I say the wrong name in the video-sorry!). On the adventure we reef our main sail for the first time, find an owl in the woods, see some deer and hang out with some fish in a lake. Thank you to Michelle D...
Breaking our Boom Vang while Wing on Wing | Chapter 2 Episode 6 | The Wayward Life
Wayward Life Sailing

Breaking our Boom Vang while Wing on Wing | Chapter 2 Episode 6 | The Wayward Life

We get closer to our otters from the day before, explore more of Valdez Island, sail home and deal with some broken and improper rigging along the way. Part 2 of 2. Pattern: Website: Instagram: Facebook: Music in this video: Forever Tomorrow: Ranner Sillard
Sailing to Gabriola & Valdez Islands | Chapter 2 Episode 4 | The Wayward Life
Wayward Life Sailing

Sailing to Gabriola & Valdez Islands | Chapter 2 Episode 4 | The Wayward Life

We sail from Nanaimo, BC to Valdez Island in the Gulf Islands and find a secret anchorage with lots of wildlife inhabitants! Pt 1 of 2 Patreon: Website: Instagram: Facebook: Music in this video: All the Colors- DJ Quads Mele Market- Chalalatas My Rain is Gone- Victor Olsson Diamond Bossa- H...
1981 Ontario 32 Boat Tour! | Chapter 2 Episode 2 | The Wayward Life
Wayward Life Sailing

1981 Ontario 32 Boat Tour! | Chapter 2 Episode 2 | The Wayward Life

We bring you on a tour of our 1980 32ft Ontario sailboat and discuss our sailboat experiences so far and our upcoming intro to sailing liveaboard course!
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