Glen,
Welcome to Sailnet and congrats on the boat. I live in Rockville, so we're neighbors as well.
Is this your first boat? What do you already know about the Chesapeake?
I'd recommend you purchase the "Guide to Cruising the Chesapeake Bay"
2007 EDITION-GUIDE TO CRUISING CHESAPEAKE BAY $35.96 BY CHESAPEAKE BAY MAGAZINE'S - (800) 596-7245 .
You really cant go wrong anywhere on the bay. But the Northern bay may be a good start. Its easy to duck into a creek if the weather kicks up something nasty or you need to refill ice for the beer at
anchor.
Watch out for ship traffic and there seems to be a insane amount of crab pots out there this year (and it seems they're just dropping them in no order at all but that another topic) There is so much to offer and the vast differences between places like Baltimore Inner Harbor, St Michaels/Oxford, Swan Creek, and the Sassafras, etc. you will have lots o fun.
Are you planning to keep the boat on the trailer? or a marina?