The Grady-White Chase 273 2008 vs Grady-White Chesapeake 290 2011 comparison sits squarely in the category of decisions where specs alone won't tell the whole story: intended use, storage, and long-term ownership costs all factor in.
Size is the most obvious dividing line here. The Grady-White Chesapeake 290 2011 measures 29,8 feet overall (2011), giving it roughly 3,8 additional feet of deck space compared to the Grady-White Chase 273 2008 at 26,0 feet (2008). Weight tells a clearer story for trailering families: the Grady-White Chesapeake 290 2011 tips the scales at 7 650 lbs - 2 807 lbs less than the Grady-White Chase 273 2008 at 4 843 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 600 hp, the Grady-White Chesapeake 290 2011 has a 100-hp advantage over the Grady-White Chase 273 2008's 500-hp ceiling - enough to notice on acceleration and at cruising speed, particularly with a full passenger load. 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 2011 is rated for 9 passengers, while the Grady-White Chase 273 2008 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 2011 could be the deciding factor.
Bottom line: Choose the Grady-White Chesapeake 290 2011 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 Chase 273 2008 is the smarter pick if you want a lighter, easier-to-trailer boat rated for 8 that costs less to run day-to-day.