125 miles from Philadelphia (2 hours and 45 minutes by car)
The small harbor town of St. Michaels was first settled in the mid-1600s, and today a sort of colonial milieu remains, what with the old-world Georgian houses and narrow little streets with perfectly imperfect brick sidewalks. This was, and is, a shipbuilding town (indeed, the inn, built in 1850, was once a shipbuilder’s house), known for its port and marinas — and for the crabbing, particularly for blue crabs, a local specialty. Sherry Manning, Hambleton’s innkeeper, will suggest steamed crabs at the nearby Crab Claw, a casual waterside joint. Try the crabcake, too, which is fried, and also the fat scallops, good broiled or fried.
Back at the inn, guests help themselves every evening to house carafes of wine — we did, and then settled happily into rocking chairs on the second floor, to watch the setting sun bounce off the sailboats. Inside, Hambleton life is (almost) as gratifying, with recently revamped rooms that are spacious and cheery, and a breakfast of French toast and French-pressed coffee, fruit, and the house pound cake, which is topped with strawberries and remarkably low in sugar — because Sherry likes to watch out for your health.
Book it: 202 Cherry Street, 410-745-3350, hambletoninn.com.
Rooms: 5, including 1 suite.
Rate per night: Starts at $245; 25 percent off midweek specials, with a minimum of 2 nights.
Snacks: Fresh fruit in bowls and a help-yourself pantry of noshes, plus cookies in the afternoon and wine in the evening.
Meals on-site: Breakfast.
Souvenir: A model skipjack kit from the gift shop at the Chesapeake Bay Maritime Museum.
While away the hours: Choose from any number of local sailboat cruises (the Skipjack H.M. Krentz departs daily from the Maritime Museum, 410-745-6080); landlubbers can opt for the 36-mile bike loop that goes to neighboring Oxford and back. Rent a bike at 305 Mulberry Street, 800-678-8980. Or just wander the shops on Talbot Street. Bonus: Guests staying in the Michener Suite get a copy of James Michener’s Chesapeake for bedtime reading.