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 1-24 of 2129 results
Spinnaker Sailing My Cozy Trailer Sailboat (MacGregor 26X)
Adventureman Dan

Spinnaker Sailing My Cozy Trailer Sailboat (MacGregor 26X)

Sailing down a 1' deep river! DDW spinnaker sailing!.... THIS is the way to end this EPIC 9 day trip! [Video 9 of 9] _____________________________________________________________________________ 🤜🏼Exclusive/early access & Help support my adventures: Business Inquires: adventuremandanbusi...
Beached Boat to Kiteboarding!
Adventureman Dan

Beached Boat to Kiteboarding!

Kiteboarding right next to my boat/home?!? 100% YES!!! This is what I have dreamed of! SO stoked to finally be flying the kite fast and free! [Video 8 of 9] _____________________________________________________________________________ 🤜🏼Exclusive/early access & Help support my adventures: Bus...
He Took Us Sailing For FREE!!! $0.00
Adventureman Dan

He Took Us Sailing For FREE!!! $0.00

What an amazing day! Big shout out to our new friend for taking us sailing. Be sure to checkout his website or give him a call to get out on Lake Champlain Sailing! [Video 7 of 9] _____________________________________________________________________________ 🤜🏼Exclusive/early access & Help suppo...
We Stripped Our Wooden Sailboat Back to Bare Wood… Again
Acorn To Arabella

We Stripped Our Wooden Sailboat Back to Bare Wood… Again

After five nonstop days sailing from Newfoundland to Maine, Arabella is finally back in the United States—and almost immediately, she's coming back out of the water. This week's episode begins with the final leg of our offshore passage from Newfoundland. Steve and Felix find everything fr...
I Do Not Want To Leave Here
Adventureman Dan

I Do Not Want To Leave Here

Just a super chill solo day.... hanging out. This is what a down day can look like. [Video 6 of 9] _____________________________________________________________________________ 🤜🏼Exclusive/early access & Help support my adventures: Business Inquires: [email protected] 🤜🏼Gear ...
Best Summer Times On A MacGregor 26X
Adventureman Dan

Best Summer Times On A MacGregor 26X

My good friend Ilya joins me once again! Together, we get into some fun adventures traveling way way up river. Further than any other sailboat has gone before. [Video 4 of 9] _____________________________________________________________________________ 🤜🏼Exclusive/early access & Help support my...
This Boat Goes Anywhere & EVERYWHERE!!! — [Day 3 of 9]
Adventureman Dan

This Boat Goes Anywhere & EVERYWHERE!!! — [Day 3 of 9]

Making the most of our last sailing trip of the summer. [Video 3 of 9] _____________________________________________________________________________ 🤜🏼Exclusive/early access & Help support my adventures: Business Inquires: [email protected] 🤜🏼Gear & Toys I Use: Other ...
She’s Back On My Boat Again! — [Day 2 of 9]
Adventureman Dan

She’s Back On My Boat Again! — [Day 2 of 9]

Maria joins me on my MacGregor 26 once again. This time there has been a few new upgrades since her last visit. As well, she broke her arm! Thankfully, nothing stops her from having a good time out on the water. [Video 2 of 9] ________________________________________________________________________...
The LAST Trip Of The Summer (Day 1 of 9)
Adventureman Dan

The LAST Trip Of The Summer (Day 1 of 9)

This is the LAST trip of an amazing summer with this new boat. My 2001 MacGregor 26X has been an incredible adventure machine. Let's make this trip count! [Video 1 of 9] _____________________________________________________________________________ 🤜🏼Exclusive/early access & Help support my...
A Quick Update From Ben
Acorn To Arabella

A Quick Update From Ben

Check out this link and help in the fight against cancer. 100% of all funds raised go directly to research and patient care at Dana Farber.
BEST Solo Boat Day Testing Upgrades
Adventureman Dan

BEST Solo Boat Day Testing Upgrades

I meant to test four main new boat upgrades... INSTEAD...... I figured out that I can steer my boat with my body! (This was done on a small/shallow body of water under calm conditions with no one nearby or downwind.) _____________________________________________________________________________ 🤜🏼Exc...
My FAVORITE Boat Upgrade (Outboard Swim Platform) [10min installation]
Adventureman Dan

My FAVORITE Boat Upgrade (Outboard Swim Platform) [10min installation]

This is by far my favorite upgrade I've made to my boat. And one of the easiest! Buy this Swimplatform: How-To Install: _____________________________________________________________________________ 🤜🏼Exclusive/early access & Help support my adventures: Business Inquires: adventuremand...
Saying Goodbye to Newfoundland—and the Man Who Inspired Arabella
Acorn To Arabella

Saying Goodbye to Newfoundland—and the Man Who Inspired Arabella

After nearly a year in Canadian waters, it's finally time for Arabella to say goodbye to Newfoundland and begin the long journey south. But there is still one adventure left. Steve returns to the Nuddick for a final attempt at establishing a new multi-pitch climbing route, this time with his l...
This Boat Did EVERYTHING! (Perfect 6 Day Trip)
Adventureman Dan

This Boat Did EVERYTHING! (Perfect 6 Day Trip)

(Video 6 of 6) End of a perfect trip I did NOT want to leave... but all good things must come to an end. Boat Upgrade Items: _____________________________________________________________________________ 🤜🏼Exclusive/early access & Help support my adventures: Business Inquires: adventuremanda...
Accidentally Sailing Faster! [MacGregor 26X cruising fun]
Adventureman Dan

Accidentally Sailing Faster! [MacGregor 26X cruising fun]

(Video 5 of 6) Docking with a tree, surfing down waves with my boat.... It's all part of the adventure! Boat Upgrade Items: _____________________________________________________________________________ 🤜🏼Exclusive/early access & Help support my adventures: Business Inquires: adventurem...
MacGregor 26X Sailing 8.1 Knots!!! (9.3mph/15kph)
Adventureman Dan

MacGregor 26X Sailing 8.1 Knots!!! (9.3mph/15kph)

(Video 4 of 6) My first time sailing FAST & FREE this fast on my MacGregor 26X! 8.1 knots DDW was a BLAST! And, a tree for a dock! What did you think of that? Boat Upgrade Items: _____________________________________________________________________________ 🤜🏼Exclusive/early access & Help ...
26′ Boat Lake Cruising (400w of folding solar)
Adventureman Dan

26′ Boat Lake Cruising (400w of folding solar)

(Video 3 of 6) Maria and I enjoy a day docked against the solid stone beach, then explore a nearby island in our own private harbor! Power Bank: Boat Upgrade Items: _____________________________________________________________________________ 🤜🏼Exclusive/early access & Help support my adven...
Can This Get Any Better? (26′ Boat + 8′ Inflatable Dock)
Adventureman Dan

Can This Get Any Better? (26′ Boat + 8′ Inflatable Dock)

(Video 2 of 6) My friends Maria joins me for some sailing adventures and testing out the new inflatable dock. Boat Upgrade Items: _____________________________________________________________________________ 🤜🏼Exclusive/early access & Help support my adventures: Business Inquires: adventure...
My Personal Paradise (Lake Champlain Day 1)
Adventureman Dan

My Personal Paradise (Lake Champlain Day 1)

(Video 1 of 6) This week I'm off on my own on the big lake! This day solo to the lake, setting up my new dock! Loving life! Making this boat ready for full time living one upgrade at a time! Check it out! Boat Upgrade Items: ___________________________________________________________________...
41 Easy & Essential Boat Upgrades (At My Own Home)
Adventureman Dan

41 Easy & Essential Boat Upgrades (At My Own Home)

Making this boat ready for full time living one upgrade at a time! Check it out! Specialty Swimplatform(Launchpad): profusionmarine.com Boat Items List: _____________________________________________________________________________ 🤜🏼Exclusive/early access & Help support my adventures: Busi...
Upgrading the Rudder and Another Trek To The Cliff
Acorn To Arabella

Upgrading the Rudder and Another Trek To The Cliff

After 3 years of service Steve makes a big change to the rudder head taking off the bronze hardware and replacing it with a more traditional wooden setup. Not too much bronze has been removed from Arabella (fortunately!), but this change will make steering much more pleasant. Then the crew makes o...
We’re Climbing a Wall No One Has Ever Climbed Before | Rock Climbing on Newfoundland’s South Coast
Acorn To Arabella

We’re Climbing a Wall No One Has Ever Climbed Before | Rock Climbing on Newfoundland’s South Coast

Months of preparation have led to this moment. After hauling hundreds of pounds of climbing and camping gear deep into Newfoundland's wilderness, we finally establish base camp beneath the Nuddick—a spectacular granite wall that, as far as anyone knows, has never been climbed. Before any firs...
Exploring Newfoundland’s Unclimbed Coastal Cliffs by Sailboat
Acorn To Arabella

Exploring Newfoundland’s Unclimbed Coastal Cliffs by Sailboat

The adventure we've been planning all winter has finally begun. After leaving the tiny outport of Francois, we make the journey north to Twillingate in search of Newfoundland's famous spring icebergs before returning to Arabella and continuing east along the remote south coast. Then come...
Buying My Dream Boat (2001 MacGregor 26X)
Adventureman Dan

Buying My Dream Boat (2001 MacGregor 26X)

This is the story of how I bought my dream power sailor boat, a 2001 MacGregor 26X for more than half of what it was originally listed for. It wasn't easy, but over the course of four days and three nights, I am one step closer to my dream of exploring EVERYWHERE in North America! ____________...
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