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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BoatFools Sailing Latest Episode
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.)
BoatFools Sailing Journey and Videos Locations
- Maine (45.253783,-69.4454689)
- Camden (44.1910592,-69.079469)
- Penobscot Bay (44.3988875,-68.9249005)
- South Bristol (43.8639715,-69.5611574)
- Harpswell (43.7864342,-69.9598343)
- Southwest Harbor Boatyard Fairway, Mount Desert Island, Maine, USA (44.279,-68.327)
- Portland (43.6590993,-70.2568189)
- Maine (46.82,-67.92361)
Support BoatFools Sailing
At WeBoating.com, we profoundly acknowledge the unwavering dedication that BoatFools Sailing invests in crafting each and every video or voyage. Their passion for delivering exceptional ocean content shines through every frame, and it's a labor of love that deserves your attention.
We invite you to watch their captivating videos here and actively engage with their content, including their social media links above. Liking, commenting, and sharing their work goes a long way in fueling their creative fire.
We're also inviting you to explore the gear, sponsorships, and boat partnerships highlighted in the videos descriptions, or directly on YouTube. By engaging with these offerings or purchasing services and items, you directly support BoatFools Sailing, their collaborators, and the brands they're associated with.
To ensure you never miss an offshore update, consider visiting their official YouTube Channel to subscribe, like, and join their community directly.
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Watch BoatFools Sailing's Latest Videos
Catch up on the most recent updates. Browse the complete video archive and Follow the journey.
Showing 1-24 of 205 results
The WORST Docking Advice EVER!
@boatfools #sailboatdocking #SailingHumor #Shorts Docking a sailboat stressing you out? Canadian Ken and I have some advice: Just think about baseball. ⚾⛵ It may not improve your docking, but it might help you last longer. Real boats, real people, real fun! Sailboats for the Rest of Us! Join us ...
The Ultimate Sailboat for the Rest of Us | Pearson 36 Pilothouse | $62,500 | Tour
Tour the rare 1980 Pearson 36 Pilothouse sailboat Brunch with Canadian Ken and Tris in Rockland, Maine, featuring dual steering helms, 45 hp Westerbeke diesel, 4.5-foot shallow draft, and indoor heated storage.
Close Call! This Boat Owner’s Mistake Could Have Been Deadly! #boatlife #wtf
@boatfools #WTF #boatlife #verybad This Boat Owner's Mistake Could Have Been Deadly! #boatlife #wtf A fuel line (or two) on your engine exhaust is a deadly combination! This is how SAVE THE DAY JAY earns his name. Real boats, real people, real fun! Sailboats for the Rest of Us! Join us for...
You Need to See the Inside of This 1971 Mariner 32 Sailboat! | $22,500 | Tour
@boatfools #mariner32 #sailboat #sailing #ketchsailboat #sailboattour You Need to See the Inside of This 1971 Mariner 32 Sailboat! | $22,500 | Tour This 1971 Mariner 32 Ketch seemed like just another old sailboat forgotten in a boat yard. When Save the Day Jay and I first spotted her, wrapped in ...
We Found a 1979 Cal 39 That’s Been Sitting in a Barn for 10 Years | Tour
BoatFools Sailing conducts a forensic marine survey of a 1979 Cal 39 Mk II barn find sailboat dry-stored for ten years, evaluating Bill Lapworth naval architecture, fiberglass integrity, and auxiliary diesel resurrection.
How Is This 56-Year-Old Hinckley Sailboat Still So Beautiful? | $85K | Tour
Tristan and Canadian Ken of BoatFools Sailing conduct an in-depth survey of Fairbourne, an exceptionally preserved 1970 Hinckley 38 classic sailboat in Maine designed by Sparkman & Stephens.
Don’t Buy A Sailboat Until You See This | Pacific Seacraft 37 | $59,900 | TOUR
@boatfools #pacificSeacraft #sailboat #sailing #bluewatersailing #sailboattour Don't Buy A Sailboat Until You See This! | Pacific Seacraft 37 | $59,900 | TOUR Is the Pacific Seacraft 37 the Goldilocks boat—not too big, not too small, but just right? And at $59,900 she could be the best deal ...
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 #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...