I actually thought about the same (because its hard to be short handed on a sailboat and sometimes there is no wind).
I tried to rent a bowrider and a center console - and here is what I found - they are nice when you have a specific destination, but otherwise no fun at all. I.e. center console in Florida Keys was fun because I could quickly go to some place interesting. But just riding around in a boat on Chesapeake got boring very very fast. I don't really need to "get anywhere", and the darn outboard noise makes me go nuts after an hour of driving.
So, my 5 cents are - for Chesapeake, unless you like fishing, powerboat seems like not too much fun. That said, you can try it for yourself - rent one and see how it goes.