Re: St. Michaels
Some have had problems with anchors dragging when anchored out by G-3. Oyster shells seems to be the issue. Make sure you set deep. Can get pretty crowded on big weekends, and Memorial Day definitely qualifies. If you have a decent dinghy, consider Leeds Creek as an alternative.
For food, we like Ava's, especially the back patio.
Where are you sailing out of? We're looking at Mem Day options now as well.