The depth restriction you face is fairly common here on the Chesapeake. In part, you need to consider how big of a boat you want. These days, people start with boats 30-40 feet quite often, so don't be afraid of getting in over your head. You already are looking at some boats with center-boards, and that is a definite way to go. Also look for boats with winged keels. I've owned 2 Pearsons with wings and think they are great on the Chesapeake.
Frankly, a boat to look at is what I currently sail -- a Pearson 33-2 (meaning the 1986-1991 models.) The earlier models have keel/centerboards that draw under 4 feet. The later models come with a wing keel that draws 4'2". I sail out of the Patapsco and do a lot of gunkholing, so shoal draft is important to me. And yes, I run aground at least a couple of times a year and have always gotten the boat off the bottom by myself, usually in very short order.
Other boats to look at that come with K/CB's are Ericsons and Sabres. Lots of coices out there to fit your needs.
SailorMitchSailing winged keels since 1989.
1.20.09 Bush's last day the end of an error !! Hopefully we still have a constitution and economy left by then.
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