I've never stayed in St. Mike's, only have made several day trips. It does sound perfect for what you want. There are several b&bs to choose from, if you do a forum search I'm sure you'd find some topics on them. There is also The Inn At Perry Cabin. It's a high end hotel with at least one rest. It is on the water also. I sent my mom and her husband there and they really enjoyed it. Even if you don't stay there, perhaps it would be nice for your special dinner.

There is at least one skipjack that I know of that still does tours, although I'm not sure if it's sunset or not.

There are several inns outside of town with pools . . Bay Cottage, Folley's Cove and the George Brooks House. See the St. Michaels web site for details . . www.StMichaelsMD.org. Also, for romantic dinners - the Shore restaurant overlooks the harbor, Town Dock has outside dining on the harbor, and Bistro St. Michaels and 208 Talbot are good choices . . . but are on the main street in town. For super-lux dining - the Inn at Perry Cabin. St. Michaels is a harbor of refuge on the Miles River which connects to the Chesapeake Bay.

Lots of shops and a wonderful maritime museum to explore . . and sailboat rides including the historic Skipjacks. Lots to do and see.

Will Workman