The first time I went to St. Michaels, Maryland, a gem of a small (pop: 1,029), historic (dating to 1677), waterfront community on the Eastern Shore of the Chesapeake, was about 35 years ago with my friend and colleague, the late Dan Fales. We were delivering a Bertram 46 from Norfolk, Virginia, to Norwalk, Connecticut, and stopped for the night. Actually, we stopped so we could have a crab dinner sitting on the porch of the Crab Claw, looking out over the Miles River and the flow of boats in and out of the harbor.
Over the years I’ve gone back whenever I was in the area, most recently a few years ago with Billy Black, the photographer, and Ken Sawyer on his custom 42-foot cruiser, Lionheart Concerto, that was designed to look like a Bugatti on the water and had a player piano in the salon. And we went back to the Crab Claw.
We also explored town, walking down the one main street, Talbot Street, lined with colorful shops, most flying American flags. And we spent much of an afternoon at the Chesapeake Bay Maritime Museum, an 18-acre institution with a large collection of Chesapeake Bay watercraft, including a restoration of an 1889 bugeye, essentially a large log canoe used for oystering. The museum includes a boat shop for restorations, and exhibits of everything from maps of the area dating to the early explorers to fairly new photographs of life on the water.
Then we headed for the Inn at Perry Cabin, built more than 200 years ago as the home of a naval commander, and now a luxury hotel with 78 rooms, two restaurants, a swimming pool, tennis courts and a golf course. We pondered our next day’s cruise while relaxing on the Adirondack chairs on the manicured lawns. If you see pictures of the inn and its looks familiar, it had a cameo role in the Wedding Crashers movie.
St. Michaels is an easy drive from Annapolis, but the real point is to arrive by boat. There are several marinas. You can walk a few blocks to the center of town from St. Michaels Marina, a modern facility with 55 transient slips for boats from 25- to 220-feet, a chandlery and a swimming pool. Read more: