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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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...
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:
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...
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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