BoatFools Sailing
Ahoy! With a reputation for being slightly dangerous enablers of dreams, this is BootFools. If you wander into our waters, we have a suspicious feeling you may be a BoatFool too. Through inspirational, educational, and often hilariously entertaining storytelling and boat tours we journey into the world of exceptional used sailboats. By offering real intel on classic, wood, and fiberglass boats - that are actually worth your time, money and imagination - we inspire people to get out onto the water and behind the helm of their own sailing vessel. This community is made up of real boats, real people, and life-changing fun. It's the place that will remind you why you fell in love with sailing in the first place. 🚨New episodes weekly. Subscribe to get on board and join the adventure, one boat at a time. (And join our Substack community for even more useful tidbits and general Boatfoolery.)
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Ahoy! With a reputation for being slightly dangerous enablers of dreams, this is BootFools. If you wander into our waters, we have a suspicious feeling you may be a BoatFool too. Through inspirational, educational, and often hilariously entertaining storytelling and boat tours we journey into the world of exceptional used sailboats. By offering real intel on classic, wood, and fiberglass boats - that are actually worth your time, money and imagination - we inspire people to get out onto the water and behind the helm of their own sailing vessel.
This community is made up of real boats, real people, and life-changing fun. It's the place that will remind you why you fell in love with sailing in the first place.
🚨New episodes weekly. Subscribe to get on board and join the adventure, one boat at a time.
(And join our Substack community for even more useful tidbits and general Boatfoolery.)
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Watch BoatFools Sailing Latest videos
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One of the TOUGHEST Small Cruisers Ever Built? Nicholson 31 for $15K | FULL TOUR
#Nicholson31 #BluewaterCruiser #SailboatTour #PocketCruiser #BoatFoolsSailing One of the TOUGHEST Small Cruisers Ever Built? Nicholson 31 for $15K | FULL TOUR Welcome back, BoatFools Nation! Today Canadian Ken and I step aboard a true offshore legend: a...
A Proper Little Yacht for the Modern Age | Eastsail All Weather 25| Full Tour
#boatfoolssailing #sailing #bluewatersailing #pocketcruiser #Eastsail25 #boattour A Newly Completed Traditional Yacht in 2026? | Eastsail All Weather 25 | Full Tour Welcome back BoatFools Nation! Today Captain Kew and I tour BLACK MAGIC, a newly comple...
This One-of-One Wooden Yacht Costs Just $95K | FULL TOUR
#boatfoolssailing #sailing #woodenboat #liveaboard #bluewatersailing #sailboattour This One-of-One Wooden Yacht Costs Just $95K | FULL TOUR This 49' Modern Wooden Cutter Left Us Speechless... Welcome back BoatFools Nation! Today Canadian Ken and I step...
Six Boats. One Atlantic Dream. Why He Chose a Cape Dory 36.
#boatfoolssailing #capedory36 #bluewatersailing #atlanticcrossing #sailboattour Six Boats. One Atlantic Dream. Why He Chose a Cape Dory 36. Welcome back BoatFools Nation! This one is a little different—and exactly the kind of story we love. Back in F...
This 1984 Swan 42 Proves Classic Yachts Still Dominate | $90K Reality Check
#boatfoolssailing #sailing #nautorswan #sailboattour #bluewatersailing #swan42 This 1984 Swan 42 Proves Classic Yachts Still Dominate | $90K Reality Check | Ron Holland Offshore Legend for $90K | TOUR Welcome aboard, BoatFools Nation! ⚓ Today Canadian...
Our ‘New’ Sailboat Is Already Fighting Back | Morgan 384
#sailing #boatfoolssailing #morgan384 #boatwork #boatprojects #sailboat Our ‘New’ Sailboat Is Already Fighting Back | Morgan 384 Canadian Ken and I are back aboard our “new-to-us” Morgan 384 as we race to get her ready for charter season in Main...
26 Feet, 2 Cabins & Only $5,400! | 1977 Parker Dawson 26 Pocket Cruiser | Full Tour
#boatfoolssailing #pocketcruiser #Budgetboat #sailboat #trailerablesailboat #boattour 26 Feet, 2 Cabins & Only $5,400?! | 1977 Parker Dawson 26 Pocket Cruiser | Full Tour As of 05/15/2026: SOLD ***Quick note: technically this boat has a swing keel, wh...
Old Boat, Big Charm | 1968 Cheoy Lee Offshore 31 for $12.5K
#boatfoolssailing #cheapboats #boattour #herreshoff #cheoylee #classicsailboat Old Boat, Big Charm | 1968 Cheoy Lee Offshore 31 for $12.5K In this episode of BoatFools Sailing, Canadian Ken and I travel to Bath, Maine — home of Bath Iron Works — to...
$100K Spent on This 1974 Pearson 35 — Offered at $29,500 | FULL TOUR
#sailing #sailboat #pearson35 #sailboatsforsale #sailboattour $100K Spent on This 1974 Pearson 35 — Offered at $29,500 | FULL TOUR $100,000 was spent refitting this Pearson 35… and it’s listed for $29,500. We went to see if it actually lives up to...
This Boat FITS in a Shipping Container! How?!
This might be Robert Perry's most unusual sailboat design - the 39-foot container boat! Check it out. Canadian Ken and I explore a truly unique cruising sailboat, an incredible feat of engineering designed to fit perfectly into a 40-foot shipping containe...
This 5-Foot Sailboat Is Built Like the Real Thing! | 1941 Bugeye Model
#boatfoolssailing #sailboat #boatbuilding #boatrestoration #modelboat This 5-Foot Sailboat Is Built Like the Real Thing! | 1941 Bugeye Model This week on BoatFools Sailing, we found something completely different… and completely captivating. At just ...
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 th...
10 Sailboats Under $10K You Can Actually Buy! #1 is ACES.
#boatfoolssailing #sailing #boatsforsale #cheapboats 10 Sailboats Under $10K You Can Actually Buy! #1 Is a ACES! Ahoy BoatFools Nation! This week **Canadian Ken and I dive back into the Maine boat market to find the 10 best sailboats for sale under $10,...
Robert H. Perry’s COOLEST Sailboat? Fits & Ships in a Container | Far Harbour 39 TOUR | $99k
#boatfoolssailing #bluewatersailing #robertperry #sailboattour #sailing Robert H. Perry's COOLEST Sailboat? Fits & Ships in a Container | Far Harbour 39 TOUR | $99k The Robert H. Perry–designed Far Harbour 39 is unlike almost any cruising sailboat eve...
The 10 Best Sailboats Under $30K in Florida — Our #1 Pick Might Surprise You
#boatfoolssailing #sailing #boatsforsale #floridasailing #beautifulboats The 10 Best Sailboats Under $30K in Florida — Our #1 Pick Might Surprise You Ahoy BoatFools Nation! This week Canadian Ken and I head south to sunny Florida to find the greatest s...
1971 Allied Seabreeze 35 Citation — A $24K Atlantic Contender | Full Tour
#boatfoolssailing #sailboattour #classicsailboat #seabreeze35 #offshorelife 1971 Allied Seabreeze 35 Citation — A $24K Atlantic Contender | Full Tour Could a $24,000 classic offshore cruiser really be considered for an Atlantic crossing? Today we take...
Why Isn’t Anyone Buying This? | A $25K Alberg 35 Bluewater Cruiser (We’d Sail Her Tomorrow)
#boatfoolssailing #alberg35 #bluewatersailboat #sailboattour Why Isn’t Anyone Buying This? | A $25K Alberg 35 Bluewater Cruiser (We’d Sail Her Now) AS OF 04/14/2026 THIS BEAUTY IS OFF THE MARKET - THE OWNER HAS FIGURED OUT A WAY TO KEEP HER. Welcome...
Top 10 Sailboats Under $25,000 You NEED to See! | New England | EP149
#boatfoolssailing #usedsailboats #budgetsailing #sailboatreview Top 10 Sailboats Under $25,000 You NEED to See! Looking for affordable sailboats for sale in New England under $25,000? In this episode of BoatFools Sailing, Canadian Ken and I count down t...
We Asked YOU to Name Our New Boat! 14 Hilarious Suggestions
#boatfoolssailing #boatnames #sailboatlife #funnyboatnames Canadian Ken and I take a stroll with ocean views to tackle one of sailing’s biggest traditions — renaming a boat. Our “new-to-us” Morgan 384 Panache needs a name with a little more person...
How Much Is a Brand New Boat Engine Worth?
The Southern Cross 28 we checked out has a nearly brand new Yanmar diesel in it! That's amazing. A new diesel, installed on a boat this size, will set you back $25k. In other words, someone has done the expensive work for you! Look for boats like this if y...
New Sailboat or Used Sailboat? That is the question. EP146
#boatfoolssailing #boatoftheyear #usedsailboats #sailing New Sailboat or Used Sailboat? That is the question. EP 146 Every year, the sailing world celebrates the Boat of the Year winners — innovative designs, cutting-edge technology, and eye-watering p...
A Rare Dutch-Built Classic | 1961 Bill Tripp Javelin 38 | $49,500! | Tour
#ClassicSailboat #BluewaterSailboat #BillTripp #boatfoolssailing A Rare Dutch-Built Classic | 1961 Bill Tripp Javelin 38 | $49,500! | Tour This Dutch-built Beauty is in San Rafael, CA, so if you're on the west coast and in the neighborhood, go check her...