When two boats share the same hull type — in this case both the Grady-White Canyon 366 2011 and the Grady-White Express 360 2009 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?

On paper these two are close siblings in the size department — Grady-White Canyon 366 2011 at 36,6 ft versus Grady-White Express 360 2009 at 39,3 ft. Weight tells a clearer story for trailering families: the Grady-White Express 360 2009 tips the scales at 14 919 lbs — 13 634 lbs less than the Grady-White Canyon 366 2011 at 1 285 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.

Both boats share a closely matched power ceiling — 1 050 hp for the Grady-White Canyon 366 2011 and 1 050 hp for the Grady-White Express 360 2009. Real-world performance will come down more to which motor is actually bolted on, its load at the time, and whether it's a 4-stroke or 2-stroke setup. Fuel capacity breaks the other way: the Grady-White Canyon 366 2011 carries 42 gallons versus 37 gallons in the Grady-White Express 360 2009. On a lake day that's negligible, but for coastal cruising or long reservoir runs the extra range matters.

Both boats are rated for 11 passengers — a good fit for a family of four or five plus guests. Comfort at capacity is another matter; the longer hull typically means more seat options and better weight distribution.