1999 Bayliner Bayliner 2855 Ciera SB; 285 SB Cruiser — Chicago, Illinois 60633

A 1999 Bayliner 2855 Ciera at Chicago, asking $18,000 through Pop Yachts. Freshwater its whole life, and the ad reads like the boat was actually used the way a Ciera is meant to be: two proper berths plus a dinette that makes a third, a head with shower, and a beam over nine and a half feet on a hull that stays a touch under thirty — the whole Bayliner argument in one boat.

Twelve thousand under the band median, and the band is the point. Affordable cabin cruisers center on $29,900; this one asks $18,000 for the same nights-aboard mission. Bayliner built these in numbers nobody else matched — parts, knowledge and the next owner are all easy to find. Survey the usual nineties points: deck core at the fittings, bellows and gimbal, every hose its age.

The web around it is worth walking. Two thousand up sits the better-built deep-V, a Monterey 276 whose price has already been cut once:

Where more boat matters more than the badge, the repowered Carver 310 Santego is thirty-one feet with brand-new engines for less:

And if the budget can double, the Regal 2565 Window Express is this mission a decade newer:

For the price of a used car and a freshwater history, this is where the walk starts: