When two boats share the same hull type — in this case both the Monterey 290 CR 2008 and the Monterey 340SY 2011 are modified 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 Monterey 340SY 2011 measures 35,3 feet overall (2011), giving it roughly 4,3 additional feet of deck space compared to the Monterey 290 CR 2008 at 31,0 feet (2008). Weight tells a clearer story for trailering families: the Monterey 340SY 2011 tips the scales at 142 lbs — 141 lbs less than the Monterey 290 CR 2008 at 1 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 power gap is worth calling out. Rated to 375 hp, the Monterey 340SY 2011 has a 75-hp advantage over the Monterey 290 CR 2008's 300-hp ceiling — enough to notice on acceleration and at cruising speed, particularly with a full passenger load. Fuel capacity breaks the other way: the Monterey 290 CR 2008 carries 142 gallons versus 21 gallons in the Monterey 340SY 2011. On a lake day that's negligible, but for coastal cruising or long reservoir runs the extra range matters.

The Monterey 290 CR 2008 is rated for up to 9 people. Passenger data for the Monterey 340SY 2011 wasn't available.