Detailed Evaluation & Buyer Recommendation
Grady-White Chesapeake 290 2009 vs Grady-White Freedom 285 2022 — Same Brand, Different Boat
The Grady-White Chesapeake 290 2009 vs Grady-White Freedom 285 2022 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.
The power gap is worth calling out. Rated to 600 hp, the Grady-White Chesapeake 290 2009 has a 250-hp advantage over the Grady-White Freedom 285 2022's 350-hp ceiling — enough to notice on acceleration and at cruising speed, particularly with a full passenger load. Fuel capacity breaks the other way: the Grady-White Freedom 285 2022 carries 214 gallons versus 206 gallons in the Grady-White Chesapeake 290 2009. 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 Grady-White Chesapeake 290 2009 is rated for 9 passengers, while the Grady-White Freedom 285 2022 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 2009 could be the deciding factor.
Bottom line: Choose the Grady-White Chesapeake 290 2009 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 Freedom 285 2022 is the smarter pick if you want a lighter, easier-to-trailer boat rated for 8 that costs less to run day-to-day.
General Boat Info
MakeGrady-White
Makenot available
ModelChesapeake 29
Modelnot available
Model Year2009
Model Yearnot available
Measurements / Dimensions
Beam9 ft. 11 in. (3.02 m)
Beam9.60 ft
Beam - Meters3.02
Beam - Meters2.93
Beam - Inches119
Beam - Inches115
Bridge clearance - DetailWith Hardtop: 9 ft. 9 in. (2.97 m)
Bridge clearance - Detailnot available
Bridge clearance - Meters2.97
Bridge clearance - Metersnot available
Bridge clearance - Inches117
Bridge clearance - Inchesnot available
Depth - DetailCockpit: 28 in. (0.71 m)
Depth - Detailnot available
Depth - Centimeters71.12
Depth - Centimetersnot available
Depth - Inches28
Depth - Inchesnot available
Draft [max] - DetailHull: 23.5 in. (0.6 m)
Draft [max] - Detail2.20 ft
Draft [max] - Meters0.61
Draft [max] - Meters0.67
Draft [max] - Inches23.5
Draft [max] - Inches26
Weight - DetailWithout Engines: 7,650 lbs. (3,470 kg)
Weight - Detailnot available
Weight - kg3469.98
Weight - kgnot available
Weight - lbs.765
Weight - lbs.not available
Width [transom] - Detail9 ft. (2.74 m)
Width [transom] - Detailnot available
Length - Feet29.75
Length - Feet28
Length overall - Detail29 ft. 9 in
Length overall - Detail28.00 ft
Length overall - Meters9.07
Length overall - Meters8.53
Length overall - Inches357
Length overall - Inches336
Draft Minnot available
Draft Min1.60 ft
Body / Hull
Hull materialFiberglass
Hull materialnot available
Hull typeModified Vee
Hull typenot available
Engine and Drivetrain
Fuel tank capacity - Detail206 gal. (780 l)
Fuel tank capacity - Detailnot available
Fuel tank capacity - Liters779.79
Fuel tank capacity - Liters810.08
Fuel tank capacity - Gal206
Fuel tank capacity - Gal214
Drive typeOutboard
Drive typeoutboard
Engine max600 hp (448 kW)
Engine maxnot available
Engine makenot available
Engine makeYamaha
Engine modelnot available
Engine modelFour-Stroke
Horsepowernot available
Horsepower350 hp
Engine 2 Engine Makenot available
Engine 2 Engine MakeYamaha
Engine 2 Engine Modelnot available
Engine 2 Engine ModelFour-Stroke
Engine 2 Horsepowernot available
Engine 2 Horsepower350 hp
Engine 2 Fuel Typenot available
Engine 2 Fuel TypeGas
Engine 2 Drive Typenot available
Engine 2 Drive Typeoutboard
Operational Info
Boat typenot available
Boat typePower