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 Rugged Classic for the Right DIY Sailor | 1971 Columbia 39 | Full Tour
BoatFools Sailing

A Rugged Classic for the Right DIY Sailor | 1971 Columbia 39 | Full Tour

@boatfools #columbia39 #BillTripp #Sailboat #Sailing #Classicsailboat They Don’t Build Sailboats Like This Anymore | Columbia 39 | Full Tour The asking price for this 1971 Columbia 39? Best reasonable offer. And for the right sailor, that could make NAIAD a very interesting opportunity. Designe...
This Herreshoff Classic Isn’t What It Looks Like | 1985 Molly’s Cove 38 $99k! | TOUR
BoatFools Sailing

This Herreshoff Classic Isn’t What It Looks Like | 1985 Molly’s Cove 38 $99k! | TOUR

@boatfools #herreshoff #classicsailboat #Sailboattour #sailing #fiberglasssailboat At first glance, GALATEA looks like the kind of classic wooden yacht that belongs to another era. Look again. This remarkable 38-foot Herreshoff-designed cruising sailboat combines the unmistakable lines, bronze ha...
Cheap Sailboats: The Dream, The Deal, and The Disaster
Lady K Sailing

Cheap Sailboats: The Dream, The Deal, and The Disaster

Cheap sailboats are still everywhere if you know where to look. In this episode, I went online and found 50 real sailboats for sale under $15,000, including older fiberglass boats like Catalina 22s, Catalina 25s, Catalina 30s, C&C sailboats, Pearson 30s, Hunters, O’Days, Islanders, Cals, Mirages...
The Best Affordable Sailboats Nobody Talks About (With Kyle Jachney) | Sailing Truth Show
Sailing Zingaro

The Best Affordable Sailboats Nobody Talks About (With Kyle Jachney) | Sailing Truth Show

Everyone chasing the cruising dream gets pointed at the same handful of "name" boats — and most of them are priced out of reach for a first-timer. So today Kyle Jachney and I are talking about the ones nobody puts on a list: the older, affordable fiberglass cruisers from the 70s and 80s th...
Only 15 Made — We Found This Rare Sailboat for $39K | LeComte 38 | TOUR
BoatFools Sailing

Only 15 Made — We Found This Rare Sailboat for $39K | LeComte 38 | TOUR

#boatfoolssailing #williamtripp #sailing #sailboatforsale #barnfind Only 15 Made — We Found This Rare Sailboat for $39K | LeComte 38 | TOUR Ahoy BoatFools Nation! Every once in a while, a boat shows up that stops us in our tracks. This is one of those boats. Canadian Ken and I were tipped off...
Cruising Lealea Christmas Eve 2025
Cruising Lealea

Cruising Lealea Christmas Eve 2025

Over last weekend, Petersburg, Alaska got more snow than ever recorded here. The Harbor Master let everyone know to clear the snow off their boats before the next storm rolls in. Merry Christmas everyone! For more sailing adventures see our other Playlists: "Honolulu: The Beginning" - &q...
Haul-out day (end of a chapter) | Sailing Sitka Ep 186
Sailing Sitka

Haul-out day (end of a chapter) | Sailing Sitka Ep 186

That’s it, that’s all. We hauled out our sailboat in Linton Bay, Panama. Watching 25,000 pounds of fiberglass, rigging, wood and belongings lifted slowly from the water is a strange mix of awe and anxiety. Boats are meant to float, not hang suspended in the air, yet here she is, cradled by straps an...
If at first you don’t succeed…
Cruising Lealea

If at first you don’t succeed…

Second try = Success! Lealea is now back in the water with fresh bottom paint and a new zinc anode. For more sailing adventures see our other Playlists: "Honolulu: The Beginning" - "Cruising Lealea in Alaska" - "Sailing the Pacific Coast" - "Sailing Back to Ha...
2025 Haulout – First try
Cruising Lealea

2025 Haulout – First try

The weather was fine. The motor was purring, The yard crew was ready. And then... For more sailing adventures see our other Playlists: "Honolulu: The Beginning" - "Cruising Lealea in Alaska" - "Sailing the Pacific Coast" - "Sailing Back to Hawaii" - &qu...
The Alberg 30: A Sailboat Design That’s Aging Like Fine Wine | TOUR [[9/7/25 SOLD!]]
BoatFools Sailing

The Alberg 30: A Sailboat Design That’s Aging Like Fine Wine | TOUR [[9/7/25 SOLD!]]

#Alberg30 #sailboattour #classicsailboat #boatfoolssailing #cruisingsailboat [[09/07/2025 SOLD]] LEGENDS Never DIE! Alberg 30 Sailboat Tour | $12,500 LEGENDS Never Die! Meet HERON, a 1968 Alberg 30 sailboat — one of the most beloved 30-foot cruisers ever built. Canadian Ken and I fell in love ...
Lealea’s New Crew Member
Cruising Lealea

Lealea’s New Crew Member

Her name is Charlotte. She's ten weeks old. For more sailing adventures see our other Playlists: "Honolulu: The Beginning" - "Cruising Lealea in Alaska" - "Sailing the Pacific Coast" - "Sailing Back to Hawaii" - "Cruising Lealea in Hawaii&quo...
Cruising Lealea: From the Boat
Cruising Lealea

Cruising Lealea: From the Boat

Laura from Cruising Lealea shares her struggles adjusting to life on land after years living on their boat. With 9 months of neglect, the vessel requires extensive cleaning, repairs, and maintenance before winter. Their plan is to tackle a full refit next summer but focus on essential tasks first.
The Only News We Really Trust: The Petersburg Pilot Vol.50 No.31
Cruising Lealea

The Only News We Really Trust: The Petersburg Pilot Vol.50 No.31

Discover the most recent local news from the charming town of Petersburg, Alaska. Explore stories on various topics including politics, crime, environment and more to stay informed about what's going on in this beautiful Alaskan community.
From the House to the Boat in under 10 Minutes
Cruising Lealea

From the House to the Boat in under 10 Minutes

Just a short walk down to the harbor to where Lealea rests in her slip next to F/V Starship. For more sailing adventures see our other Playlists: "Honolulu: The Beginning" - "Cruising Lealea in Alaska" - "Sailing the Pacific Coast" - "Sailing Back to Hawaii&q...
The Only News We Really Trust: The Petersburg Pilot 7/25/24
Cruising Lealea

The Only News We Really Trust: The Petersburg Pilot 7/25/24

In this week's Petersburg Pilot News, we explore stories about Pia building new infrastructure, Arts Festival at Kaufman Cove, an upcoming election affecting 14 local positions, a successful beach san operation for king salmon restoration, and more. Get caught up on everything happening in Pete...
The Only News We Trust: The Lealea Crew Reads the Newspaper
Cruising Lealea

The Only News We Trust: The Lealea Crew Reads the Newspaper

Join the Lealea Crew as they present real, truthful news right from their hometown of Petersburg, Alaska, by reading through the weekly Petersburg Pilot newspaper. From front page stories about potential debt for a water project to discussions on abandoned vessel disposal costs, experience the local...
Summer 2024 – Video 487
Cruising Lealea

Summer 2024 – Video 487

Experience a unique adventure of horse sitting on an island, overlooking stunning scenery while caring for arthritic horses. Join us as we explore the tranquil life of this small community and bond with the aging equine companions.
Cruising Lealea: Status Report March 2024
Cruising Lealea

Cruising Lealea: Status Report March 2024

Chuck and Laura bringing everyone up to date on our Lealea lives in Alaska For more sailing adventures see our other Playlists: "Honolulu: The Beginning" - "Cruising Lealea in Alaska" - "Sailing the Pacific Coast" - "Sailing Back to Hawaii" - "Crui...
Cruising Lealea: New Stuff
Cruising Lealea

Cruising Lealea: New Stuff

Lots of changes but still "Cruising Lealea" For more sailing adventures see our other Playlists: "Honolulu: The Beginning" - "Cruising Lealea in Alaska" - "Sailing the Pacific Coast" - "Sailing Back to Hawaii" - "Cruising Lealea in Hawaii...
A Gem In The City | Ep. 35 | Sailing With Friends Around Victoria, Canada
Sailing Sea Dream of Clyde

A Gem In The City | Ep. 35 | Sailing With Friends Around Victoria, Canada

Ahoy sailors and sailing enthusiasts! It has been a little while since my last video, and may be a little while before the next, but here is a quick one from late this spring when my friends Taryn and Logan from @WaywardLifeSailing joined me aboard Sea Dream of Clyde for a night out at anchor. We se...
Adventures/Misadvantures…and the VA Healthcare System
Cruising Lealea

Adventures/Misadvantures…and the VA Healthcare System

It's just our life... For more sailing adventures see our other Playlists: "Honolulu: The Beginning" - "Cruising Lealea in Alaska" - "Sailing the Pacific Coast" - "Sailing Back to Hawaii" - "Cruising Lealea in Hawaii" - "Sailing f...
Cruising Lealea
Cruising Lealea

Cruising Lealea

To view the complete Cruising Lealea Refit Playlist, click the link! For more sailing adventures see our other Playlists: "Honolulu: The Beginning" - "Cruising Lealea in Alaska" - "Sailing the Pacific Coast" - "Sailing Back to Hawaii" - "Cruisin...
Cruising Lealea LIVE 10-09-2022 Tourist Season is Over
Cruising Lealea

Cruising Lealea LIVE 10-09-2022 Tourist Season is Over

Preparing Lealea for Winter, Local News, BIG Plans, Exciting happenings, Questions? Answers! For more sailing adventures see our other Playlists: "Honolulu: The Beginning" - "Cruising Lealea in Alaska" - "Sailing the Pacific Coast" - "Sailing Back to Hawaii&q...
10-06-2022 North Harbor, Petersburg, Alaska
Cruising Lealea

10-06-2022 North Harbor, Petersburg, Alaska

Just enjoy the view while I do my Thursday chores. For more sailing adventures see our other Playlists: "Honolulu: The Beginning" - "Cruising Lealea in Alaska" - "Sailing the Pacific Coast" - "Sailing Back to Hawaii" - "Cruising Lealea in Hawaii&q...
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