Both the Grady-White Canyon 283 2011 and the Grady-White Chesapeake 290 2012 are modified-V designs, both built in fibreglass, so 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 283 2011 at 28,0 ft versus Grady-White Chesapeake 290 2012 at 29,8 ft. Weight tells a clearer story for trailering families: the Grady-White Chesapeake 290 2012 tips the scales at 7 650 lbs - 1 786 lbs less than the Grady-White Canyon 283 2011 at 5 864 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 - 600 hp for the Grady-White Canyon 283 2011 and 600 hp for the Grady-White Chesapeake 290 2012. 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. Both carry nearly identical fuel loads - 205 gal and 206 gal - so range won't be a tiebreaker here.
For family outings this is probably the sharpest distinction between the two. The Grady-White Chesapeake 290 2012 is rated for 9 passengers, while the Grady-White Canyon 283 2011 caps at 8. If you're regularly pulling extended family or a group of friends onto the water, the extra seats on the Grady-White Chesapeake 290 2012 could be the deciding factor.
Bottom line: Choose the Grady-White Chesapeake 290 2012 if your priority is putting more people on the water - it handles 9 passengers and at 29,8 ft it has the deck room to back that rating up comfortably. The Grady-White Canyon 283 2011 is the smarter pick if you want a lighter, easier-to-trailer boat rated for 8 that costs less to run day-to-day.