When two boats share the same hull type — in this case both the Bayliner 255 Cruiser 2013 and the Bayliner 285 SB 2011 are deep vee designs with fiberglass construction — the buying decision usually comes down to a handful of practical questions: how many people are you putting on the water, how far do you trailer, and what does your tow vehicle weigh?

Size is the most obvious dividing line here. The Bayliner 285 SB 2011 measures 28,6 feet overall (2011), giving it roughly 3,5 additional feet of deck space compared to the Bayliner 255 Cruiser 2013 at 25,1 feet (2013). Weight tells a clearer story for trailering families: the Bayliner 285 SB 2011 tips the scales at 8 056 lbs — 7 408 lbs less than the Bayliner 255 Cruiser 2013 at 648 lbs. That difference is meaningful if you're working within a half-ton or three-quarter-ton truck's tow rating, especially once you factor in a motor, gear, and fuel.

The Bayliner 285 SB 2011 tops out at 380 hp. Engine specs for the Bayliner 255 Cruiser 2013 aren't listed — confirm with a dealer before selecting an outboard.Fuel capacity breaks the other way: the Bayliner 285 SB 2011 carries 89 gallons versus 7 gallons in the Bayliner 255 Cruiser 2013. On a lake day that's negligible, but for coastal cruising or long reservoir runs the extra range matters.

For family outings this is probably the sharpest distinction between the two. The Bayliner 255 Cruiser 2013 is rated for 8 passengers, while the Bayliner 285 SB 2011 caps at 1. If you're regularly pulling extended family or a group of friends onto the water, the extra seats on the Bayliner 255 Cruiser 2013 could be the deciding factor.