[JohnRPollard]

Chuckles' boat sounds nice, but I think you could get away with something smaller than 25'.

In your place, I'd be looking for something in the 17-20' range. It would be good if that hull had a fair bit of V below the waterline and likewise a moderate amount of flare above -- the Chesapeake chop can be tiresome and wet with a shallow-deadrise, low flare hull (such as you often see on lakes).

A single reliable outboard is all you'd need, probably in the 150-200 hp range. There are some models with inboard diesels that would be heavier duty and less costly to operate (but more expensive to purchase).

You didn't mention price range, but I would look at some of the larger Boston Whalers, starting at 17 feet. There is an 18 foot model, I believe, that even has a head tucked under the center console steering station -- if that's a priority. Another one that would fit the bill nicely is the +/- 18 foot Seacraft.

Those are two to start with, for comparisons sake, but there are loads of similar boats. You should be able to choose from a wide variety.