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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Showing 1-24 of 196 results
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...
Did Our Charter Gambit Work? | Mid Season Update
@boatfools #sailboatcharter #bareboatcharter #morgan382 #morgan384 #sailingmaine Did Our Charter Gambit Work? | Mid Season Update Was putting our own sailboats into charter a brilliant idea—or a terrible mistake? We're halfway through our first charter season, and it's time for an hone...
3 Years After We Featured This Boat…We’re Back Aboard! | Southern Cross 39 | Full Tour
@boatfools #southerncross #sailboatrefit #bluewatersailing #sailing #diyboat 3 Years After We Featured This Boat…We’re Back Aboard! | Southern Cross 39 | Full Tour Three years ago, Canadian Ken and I traveled up the Penobscot River to Winterport, Maine, to check out a very special sailboat: South...
We Tour a Norseman 447: Is This the Perfect Offshore Sailboat? | A $139,500 Bob Perry Classic
@boatfools #Norseman447 #RobertyPerry #bluewatercruiser #sailing #yachttours We Tour a Norseman 447: Is This the Perfect Offshore Sailboat? | A $139,500 Bob Perry Classic Why do so many sailors love the Norseman 447? In this episode of BoatFools Sailing, Green Mountain Josh returns for his first ...
Would You Save This Beautiful Swedish Hallberg Mistral 33 Sailboat? | $12k | Tour
#hallbergrassy #hallbergMistral33 #sailboat #Sailing #boattour #boatfools Would You Save This Beautiful Swedish Hallberg Mistral 33 Sailboat? | $12k | Tour Would you save this beautiful Swedish yacht? In this episode of BoatFools Sailing, Canadian Ken and I tour a classic 1970 Hallberg Mistral 33...
Is This Sweden’s Best Kept Secret | 1985 Scanmar 35 at $29,500 | Full Tour
#boatfools #sailing #SwedishSailboat #bluewatersailing #centercockpit Is This Sweden's Best Kept Secret | 1985 Scanmar 35 | Full Tour Join Canadian Ken and me as we tour one of the most intriguing—and least-known—bluewater cruising sailboats ever built. We had an absolute blast exploring this...
Is This Luders 33 Sailboat The One? | $25,000 | Full Tour
#BoatFools #sailing #luders33 #boattour #sailboat Is This Luders 33 Sailboat The One? | $25,000 | Full Tour What happens when someone spends six years searching for the right sailboat? Meet Sophia. For the past six years, she's been working with our good friend Captain Kew or Q (who unfort...
20 Feet of Awesome! | Nordica 20 Micro Cruiser | Full Tour
#nordica20 #pocketcruiser #microcruiser #trailersailer #boatfoolssailing #sailing 20 Feet of Awesome! | Nordica 20 Micro Cruiser | Full Tour The Nordica 20 is one of the most capable micro cruisers (or "pocket cruisers") ever built—and Canadian Ken and I loved it! Designed by Malta-Mull...
Is This The Ultimate Island Cruiser? | 1985 Irwin 43 MKII Full Tour
#boatfoolssailing #irwin43 #sailboat #islandcruiser #sailing #sailboattour Is This The Ultimate Island Cruiser? | 1985 Irwin 43 MKII Full Tour Join Captain Kew and me as we step aboard S/V Dream, a beautifully maintained 1985 Irwin 43 MKII, a spacious center cockpit cruising sailboat that's ...
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 beautifully maintained 1978 Nicholson 31 sa...
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 completed Eastsail All Weather 25—a traditional fu...
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 aboard something truly extraordinary —...
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 February, Andrew flew all the way from Norway t...
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 Ken and I step aboard a true offshore thoroug...
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 Maine… but like every old sailboat, she has a few opinio...
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, which is 1,100 lbs, and locks in the down ...
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 step aboard a beautifully cared-for 1968 Cheoy ...
$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 the numbers. This week we’re in Warwick, Rhode I...
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 container. This clever container design allows ...
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 5 feet long, this handcrafted 1941 Bugeye mode...
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...
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 $10,000. Some of these boats are incredible barg...
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 ever built. This remarkable boat was cre...