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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A GORGEOUS and RARE Sailboat for Sale at $25,000! One of Only 23 Vineyard Vixen 34s Ever Built. SOLD
BoatFools Sailing

A GORGEOUS and RARE Sailboat for Sale at $25,000! One of Only 23 Vineyard Vixen 34s Ever Built. SOLD

#SailboatForSale #VineyardVixen #BluewaterSailboat #BoatFoolsSailing #Sailing #Sailboats #CruisingLife #Liveaboard #SailingLifestyle #boatforsale A GORGEOUS and RARE Sailboat for Sale at $25,000! One of Only 23 Vineyard Vixen 34s Ever Built. [[SOLD!]] Update 05/13/2025: SOLD! About a month ago, ...
Our FAVORITE TRICK to Make Raising the Mainsail EASIER!
Out Chasing Stars

Our FAVORITE TRICK to Make Raising the Mainsail EASIER!

If you want to go sailing, you need to raise the mainsail. It can be like an intricate dance, and it's incredibly frustrating when that dance gets interrupted due to a questionable lazy jack design. We've come up with a way move the lazy jacks outboard and create a lot more room to raise...
Birds of a Feather (Calico Skies Sailing Ep. 35)
Calico Skies Sailing

Birds of a Feather (Calico Skies Sailing Ep. 35)

They say Birds of a Feather Flock Together and that's exactly what transpires in this episode! We are lucky to cross paths with Dan and Kika of @Sailing Uma and like it often happens in the cruising lifestyle we become friends quickly and get right to the business of having fun. Together we enj...
Summertime and the Livin’s Easy; Spinnaker Sailing on Lake Bra’s Dor (Calico Skies Sailing Ep. 34)
Calico Skies Sailing

Summertime and the Livin’s Easy; Spinnaker Sailing on Lake Bra’s Dor (Calico Skies Sailing Ep. 34)

It's time to explore a new part of Nova Scotia's Lake Bras Dor, and as we're starting to realize, there seems to be no end to great sailing days on this beautiful lake! First, we set out with a gorgeous downwind sail, and take the opportunity to explain a bit behind the process of set...
Happy Holidays from Calico Skies Sailing!
Calico Skies Sailing

Happy Holidays from Calico Skies Sailing!

Real time update coming at ya!! We're getting Calico Skies decorated for Christmas and because we're underway it's gotta be done sailboat style (aka can survive heeling). Check out our creative way of putting up 'our tree' and find out what we've been getting into latel...
Lake Livin’: Sailing Lake Bras d’Or (Calico Skies Sailing Ep. 33)
Calico Skies Sailing

Lake Livin’: Sailing Lake Bras d’Or (Calico Skies Sailing Ep. 33)

In this episode, we get busy living our best life on Lake Bras d'Or, Nova Scotia. We pass the time paddling, hiking, making bon fires, and occasionally moving Calico Skies to a new cove for a change in scene. We’re beginning to understand the allure of lake sailing and enjoy experiencing its va...
Sailing Nova Scotia: A Cruiser’s Playground (Calico Skies Sailing Ep. 32)
Calico Skies Sailing

Sailing Nova Scotia: A Cruiser’s Playground (Calico Skies Sailing Ep. 32)

This episode sets the theme for our first Canadian Cruising Experience: A little thing we like to call Adult Summer Camp! First, we set sail and head into Lake Bras’dor by navigating the famous St. Peter's Lock. Once anchored, we do some provisioning in the nearby town. And then its finally tim...
This is Bliss: Offshore Sailing at it’s Finest (Calico Skies Sailing Ep. 31)
Calico Skies Sailing

This is Bliss: Offshore Sailing at it’s Finest (Calico Skies Sailing Ep. 31)

Sailing is about the journey, not the destination and this episode is evidence of that. It begins on the fifth day of our 1,000 mile passage from North Carolina to Nova Scotia, Canada. We continue to encounter light but favorable winds and comfortable seas. As we make our way through the Atlantic we...
Offshore Sailing & The Gulf Stream: Riding the Magic Carpet North (Calico Skies Sailing Ep. 30)
Calico Skies Sailing

Offshore Sailing & The Gulf Stream: Riding the Magic Carpet North (Calico Skies Sailing Ep. 30)

In this episode we set out on our 1000 mile sailing passage to Canada. Initially we encounter steep waves and choppy seas off Beaufort NC but offshore conditions mellow out considerably. We utilize Predictwind and our Iridium Go satellite phone to optimize our routing and keep ourselves moving wel...
The Great Escape: Hello Sailing, Goodbye East Coast! (Calico Skies Sailing Ep. 29)
Calico Skies Sailing

The Great Escape: Hello Sailing, Goodbye East Coast! (Calico Skies Sailing Ep. 29)

Temperatures are soaring here in Beaufort, North Carolina, but that does little to slow us down. In this Episode, we do some more provisioning, and Bill finishes the autopilot repair. Then he cleans Calico’s bottom and we’re finally ready once again to set sail for Canada - That is, until we go to s...
Finding Our Sister Ship; 2 of Only 6 IN THE WORLD!! (MJ Sailing – EP 54)
MJ Sailing

Finding Our Sister Ship; 2 of Only 6 IN THE WORLD!! (MJ Sailing – EP 54)

There have only been 6 of our boats made in the world, so imagine the surprise when we wake up in the morning and find out that our sister ship has anchored right next to us! This channel is made possible by viewers like you. Please help us keep this channel creating great content by becoming a pa...
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