The $25K Comeback Tour (New England Edition)
After “Adapt or Die,” we brought it back to Earth — and found 10 sailboats worth loving.
A few editions ago we wrote “Adapt or Die” — the one where we stared into the abyss of modern boat pricing and asked the uncomfortable question:
Is the future really a $700,000 production boat… or can we still fall in love with older boats that are actually attainable?
This week, Canadian Ken and I decided to answer that the only way BoatFools knows how:
By going hunting.
Not for unicorns. Not for fantasy listings.
For real, buyable sailboats — the kind that can get you out on the water this season without selling a kidney.
So here it is: 10 sailboats for sale in New England for $25,000 or less.
Some are classic. Some are oddballs. A couple are priced like someone’s ex is involved. But they all have one thing in common:
They’re the antidote to “Adapt or Die.”
Some of you may have seen this episode on YouTube and some of you may have not. Either way, read on! Not gonna lie, these are some really good looking boats, especially for this price range.
The 10 Boats (Under $25K)
1) The “Wait… WHAT?” Head-Turner
1996 Custom Chuck Paine “Rose 30” (Cold-Molded) — $25,000 — Brooklin, Maine
We opened with a banger.
A custom-built, cold-molded Chuck Paine design with serious Morris Yachts vibes — the kind of boat that makes you stop scrolling mid-doom.
Cold-molded (quickly) = thin wood layers built over a form, then glassed/composited into a hull that can be strong, stiff, and light when done right. According to the seller, the builder spent 12 years on it and was (in the best way) obsessive.
What we liked:
A proper, confidence-inspiring underbody: skeg-hung rudder, protected prop/aperture, and generally “this was built by someone who cared”
Useful cruising gear: dodger/bimini setup, lazy jacks, roller furling
Diesel, autopilot, diesel heater, newer electronics (AIS/plotter), and a 2022 survey
Extras that actually matter (stands, dinghy/outboard, etc.)
If you love Chuck Paine lines and that Tom Morris “quietly right” look, this is your catnip.
2) The Big-Boat Curveball
1984 Belliure Sloop Spanish-Designed 41’ Cutter — $24,995 — Tiverton, Rhode Island
This one made us do the thing where you lean closer to the screen and mutter:
“What’s the catch?”
Because at $24,995 you don’t usually land a 41-foot cutter that looks legitimately offshore-minded.
What stood out:
High coamings, big bridgedeck, stout “go somewhere” energy
Layout that’s a bit different from the usual order — and two heads
Huge tanks (water and diesel numbers in the listing/data were eye-watering)
The general vibe of a boat that could swallow a sea state and ask for seconds
The one big asterisk:
Volvo Penta with 4,000+ hours. Could be “half-life,” could be “fine forever,” could be “survey says no.”
Either way: worth a hard look, because boats like this don’t usually show up at this number unless there’s a story.
