Thoughts on a mid size cruising boat
I also sail on the Chesapeake. There are big differences between sailing the upper, middle, and Lower Bay but in a general sense the Bay offers light air punctuated by heavier air, with little in between. The Bay tends to kick up a pretty steep chop and tends to require beating and dead downwind courses more than anything else. As a result the Chesapeake rewards boats that sail well on all points of sail and in a wide range of windspeeds than anywhere else that I have sailed in my life.
The usefulness for light air performance and a little more speed has little to do with racing on the Bay and everything to do with having a greater number of sailing days and a fewer number of engine hours. It has more to do with having options where to anchor for the night or in some of the lower reaches of the Bay, being able to cover the relatively long distances between sheltered places to lay in for the night.
Boats designated as ''racer cruisers'' usuallly have a little less weight and a little more sail area than your average cruiser and so are ideal for the Bay. For most people a good performing coastal cruiser will work well on the Bay. There are few places to hit rocks and enough places to duck in that heavy duty cruisers are not necessary and with their poorer sailing performance are often next to useless as sailboats on the Bay.
Boats like Beneteau''s First series, Hunters and Catalina''s make reasonably good choices in the Bay''s somewhat protected environment but there are also a lot of other options out there in your price range.
I keep hearing people talk about how shallow the Bay is but I sail a boat with 6''-4" draft and frankly I have not found that draft to be a problem.
Within your price range boats like the following work well on the Bay:
Beneteau First 305
Beneteau First 32s5
Beneteau First 345
Beneteau First 35
Beneteau First 35s5
C&C 35 III
Dehler Optima 101 (one of my favorites on this list)
Ericson built Olsen 34 (This is a really neat boat for the Bay.)
Goman Express 30
Farr 1020 (Farr 11.2) Probably my favorite on this list in terms of a balance of sailing ability, build quality and accomodations)
Hunter Legend 35.5
J-34c (not to be mistaken for the J-34 that was a race boat this boat is part of J-boats cruising series and an extremely nice boat.)
Tartan 34 mk II
Thomas 35 (Tartan)