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 119 results
Annapolis Sailboat Show 2026 FULL Tour
Adventureman Dan

Annapolis Sailboat Show 2026 FULL Tour

Adventureman Dan explores the 2026 Annapolis Sailboat Show at City Dock on the Chesapeake Bay, inspecting world-cruising monohulls, luxury catamarans, cutting-edge ground tackle, and innovative offshore sailing hardware.
Leaving My Home
Adventureman Dan

Leaving My Home

Adventureman Dan departs his upstate New York family home with his $17,000 MacGregor 26X UMAR rig, trailing south to the Annapolis Sailboat Show.
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...
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 ...
This Is My Home (Anywhere & Everywhere)
Adventureman Dan

This Is My Home (Anywhere & Everywhere)

A full day with my good friend Ilya. What a blast! And SO much inspiration for the future! (I am now planning on making adjustments to my boat so it can WAKE SURF!!!!...... but don't tell anyone!) [Video 5 of 9] _____________________________________________________________________________ 🤜🏼Ex...
Best Summer Times On A MacGregor 26X
Adventureman Dan

Best Summer Times On A MacGregor 26X

Dan of Adventureman Dan tests the MacGregor 26X trailerable motorsailer on inland waterways, navigating shallow sandbars, water ballast dynamics, and off-grid cruising logistics.
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...
Crazy Good Deal Or Disaster Waiting To Happen?
Adventureman Dan

Crazy Good Deal Or Disaster Waiting To Happen?

SO many upgrades! Tow vehicle + boat trailer + solar panels + DIY bimini build & plans for heading South in time for the Annapolis Sailboat Show on October 15th! _____________________________________________________________________________ 🤜🏼Exclusive/early access & Help support my adventur...
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...
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...
Dream Destination/Near Disaster (Macgregor 26X Cruising)
Adventureman Dan

Dream Destination/Near Disaster (Macgregor 26X Cruising)

The finally conclusion to this incredible week of cruising and exploring Lake Champlain! Culminating with getting my power sailboat "Adventureborne II" right up and nearly against a massive waterfall! What an adventure! ______________________________________________________________________...
26′ Power-Sailboat Cruising Lake Champlain (Go ANYWHERE)
Adventureman Dan

26′ Power-Sailboat Cruising Lake Champlain (Go ANYWHERE)

My fifth time taking this boat out and I'm back on Lake Champlain with my good friend Ilya once again. Together we cruise lake Champlain during the 4th of July for an EPIC week of fun! Easter Egg Link To Part 2: _____________________________________________________________________________ 🤜...
*The Announcement Video*
Adventureman Dan

*The Announcement Video*

Several major announcements: 1. I'll be fully nomadic September 15th. 2. I'm leaving New York State and driving down the entire East Coast, Maine to Florida by December. Then to the Bahamas in January for several months. 3. I'm going to the Annapolis sailboat show October 15th-18th. 4...
WeBoating
Logo
Shopping cart