Long known as a home away from home for Washington, D.C.’s elite, Maryland’s Eastern Shore is no longer only for Beltway insiders. An easy 90-minute drive from D.C., 2.5 hours from Philadelphia and just under four from New York, the sleepy waterside village of St. Michaels blends small-town charm with the luxury that comes in its Forbes Travel Guide Four-Star escape, Inn at Perry Cabin by Belmond.
If the building’s genteel white exterior seems familiar, you might recognize it from the popular 2005 film Wedding Crashers, where it served as the backdrop for many of the movie’s reception scenes.
The perfect weekend is closer than you think. If you’re departing from the nation’s capital, opt to “Skip the Bridge” with the inn’s aptly named package and meet its 55-foot Hinckley yacht at a private dock near Annapolis. Hop aboard for an hour-long cocktail cruise across the Chesapeake Bay and up the Miles River, where you’ll land right at the edge of the waterfront property, much as a well-heeled guest would have centuries before.
Don’t worry about a car; it’s easy to walk the entire town on foot. Should you prefer wheels, take advantage of a fleet of bicycles or the resort’s BMW shuttle service to get around.
Check into one of the inn’s 78 recently refreshed accommodations (we highly suggest choosing one of 30 suites — several offer water views) done up in cool gray and blue tones to highlight the natural beauty of the sparkling water, lush landscaping and rolling green lawns right outside your private patio or balcony. In cooler months, request a ground-floor room with a working fireplace. Many of the units feature ornate details inspired by the property’s 19th-century heritage.
Spend your first evening strolling the grounds, taking in a quick round of bocce or croquet, or sipping a sunset cocktail from an Adirondack chair before dinner at Stars, the resort’s Forbes Travel Guide Recommended seafood restaurant.
For a taste of the region’s bounty, we’d suggest ordering the crab cakes — a delicious mixture of lump crab and minimal filler lightly fried to a crispy exterior — or local striped bass with fresh seasonal vegetables.
By Sea and By Land
You’ll dine here again in the morning — ideally on the hydrangea-covered patio — listening to the waves lap against the dock as you sip your morning coffee and savor a made-to-order omelet as you wait for Captain Jason, head of the resort’s water sports program, to let you know that your boat is ready.
Perry Cabin’s fleet is available for private charter, sailing lessons or group excursions along the Bay. We love the 40-foot Friendship Stargazer, a beautiful handcrafted sailboat that boasts a particularly smooth ride and wide bow, ideal for sunbathing on warm days.
As you step back on land, gather those newly acquired sea legs for a bike ride to town, where Main Street has shops packed with knickknacks and antiques galore. Local favorites include Guilford & Company, with its silver jewelry and vintage gems; American/Holiday offering unique home décor; The Preppy Redneck for clothing; and, of course, The Christmas Shop for a year-round selection of inspired ornaments.
After your shopping spree, you could head off to explore the Chesapeake Bay Maritime Museum or try a flight at local rum- and whiskey-makers Lyon Distilling Co. or a pint at Eastern Shore Brewing. You could also just unwind by the inn’s infinity-edge pool or try tennis on one of the property’s three brand-new Har-Tru courts.
As the sun sets, stroll back to town for authentic Italian fare at Limoncello, a casual local haunt run by Naples, Italy, transplants Ivano Scotto and Gennaro DiBenedetto. The signature limoncello martinis are worth the splurge, as are the housemade pastas. End your evening with a scoop at Justine’s in town, or a nightcap at the on-property Purser’s Pub.
Take it easy on Sunday morning with a round of golf at the inn’s new Links at Perry Cabin, a Pete Dye-designed course, or opt for a botanically infused treatment at the recently updated spa. A cup of tea on the spa’s garden patio is one of the most relaxing ways we can think of to end the weekend.
As you board the Hinkley once more for your ride home, you’ll wonder why everyone doesn’t eschew city life for small-town, waterfront living.