Maybe it's the proximity to the Naval Academy, or the strong bay breezes, or the plates of boiled crab at the dock, but Saint Michaels could be the East Coast's top sailing town. From Annapolis, it's a half-day sail across the Chesapeake – passing the wooded shoreline along Wye Island, taking in the herons, osprey, and plantation-era estates like Old Martingham – before tying up at the St. Michaels Marina. On weekends, the town is crawling with K Street players, but the dock crowd has the real fun. Local sailors meet for Saturday log-canoe races. On summer Wednesdays, they get serious and race on the Miles River, a wide, smooth tidal tributary. "We call it Miles Lake," says Mike Kabler, 44, a lifelong sailor in these waters. "It's so nice we never leave it." Summer mornings, St. Michaels Crab and Steak House is jammed for the veggie-infused Bloody Marys, paired with a dozen large steamed crabs. It starts to clear out for the afternoon golfers' tee times at the par-70 Harbourtowne golf course. By nightfall, the sleep-in boats at the docks are lit up, bobbing to music, with wine bottles on deck and people pulling on sweaters. The early rowdy crowd hits Talbot Street. But the sailing set wait for their evening buzz to kick in, then head to the Carpenter Street Saloon, one of the few places to stay open until 2 a.m.
Getting there: St. Michaels Crab and Steak House is just down the street from the Marina. Area hotels range from $65 to $150 per night.