Personally, I'd skip Solomon's and head
to eastern shore. St. Michaels is a great place to visit. I like Wye River, but there are lots of other spots too. I'm not a seasoned Chesapeake cruiser - disclaimer.
Looking for backwater or restaurants/shopping? Don't know if you spend much time in Annapolis, but it's worth picking up a mooring
there too. Try Chick and Ruths deli for breakfast. I had a blast up there last summer...