How about the eastern shore??
I bought my H 29.5 through Tidewater. They are very knowledgeable but I agree with prior post about the sailing conditions up that end of the bay. The Middle river just above Baltimore is very nice and there are several sailor's marinas. I spent a year at Bowley's (www.bowleysmarina.com) The Magothy is very nice but the good marina (www.magothymarina.com) is at the western/inner end of the river. Annapolis is too busy for me. Suggest you check out Rock Hall (www.rockhallmd.com) on the eastern shore opposite Baltimore. We are in Haven Harbour (www.havenharbor.com) going on our 3rd season and love it. Great place, peaceful and quiet, and an easy sail south west to the Magothy or Annapolis, north to Fairlee or Warton Creeks or the Sassafras,and south to Kent Island or St. Michaels, and don't forget the many creeks off the Chester River. Also, for moorings, check out Swan Creek Marina(www.rockhallmd.com/swancreek) All have great sailing, more sail than power boats, and lots of beautiful spots for some quiet time. Good Luck in your search.