We Reviewed 31 Sailboats This Year. 17 Sold. Here's What Happened
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What Sold, What Sat, and Why. A Wild Year in Sailboats! (BoatFools 2025 Review)
2025 was a BIG year for BoatFools Sailing.
Canadian Ken and Tris take a hard look back at the sailboats we profiled, the ones that sold, the ones that surprised us by not selling — and what it all says about the used sailboat market heading into 2026.
This year, we toured 31 sailboats across the Maine - and one in Massachusetts.
👉 17 of them sold in 2025 — a 55% success rate
(Slightly down from 2024’s 63%, but still strong in a shifting market.)
Chapters:
00:00 Opener - 2025 was Fun!
00:38 Intro - Year in Review
02:36 And the First Two Winners Are?
05:04 And The Next Two Winners Are?
07:58 And the Last Two Winners Are?
11:39 Green Mountain Josh's Holiday Wishes
12:08 Captain Kew's Holiday Wishes - and a Snowball to His Face!
12:41 An Elf Visits Us Serving Holiday Cheer
13:52 Our First Two Favorites That Didn't Sell
16:01 The Last Two Sailboats That Didn't Sell
19:47 Final Thoughts
* The Boats We Loved — and That SOLD
Canadian Ken’s Picks:
-Morris Justine 36 (Chuck Paine design excellence)
-Custom Carbon Fiber Muscongus Bay 18
-A stunning Custom John Alden–designed 47-footer
Tris’ Picks:
-Pearson Countess 44
-Allied Seawind II (descendant of the first fiberglass circumnavigator)
-Bayfield 25 Pocket Cruiser — proof that small boats still matter
* The Boats That Didn’t Sell — and Why We’re Surprised
Ken’s head-scratchers:
-Pearson 365 Ketch
-Herreshoff-designed Bristol 30
Tris’ surprises:
-Pearson Wanderer 30
-Cheoy Lee Clipper 36 (with a brand-new Nanni diesel)
*More Than Just Boats
2025 also brought:
More adventures with Green Mountain Josh. Tris and Josh had a killer 5-day cruise with great friends on 4 other boats in tow. Hopefully Canadian Ken can make 2026's cruise.
Captain Alan Kew (Captain Q) joining the BoatFools crew. We profiled 3 boats together and had a ball. More to come!
The launch of The BoatFools Report - nearly 4,000 subscribers strong! Thank you.
Growth of our Boat Buying Consulting Business with Captain Kew. Between the 4 of us, we have nearly 200 years of collective sailing experience.
New friends, great laughs, and some truly beautiful boats.
This video isn’t just a recap — it’s a real-world look at what actually moves boats, what doesn’t, and what buyers should be thinking about next.
⚓ Thanks to all of you who watch, comment, support, and share.
You make BoatFools possible.
Happy Holidays to All!
See you in 2026.
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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We Reviewed 31 Sailboats This Year. 17 Sold. Here's What Happened Location
- Maine (45.253783,-69.4454689)
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