As part of a series on long weekend getaways, we’re showing you how to make the most of your summer Fridays, school breaks and the season’s extra-long days. Check back every week for inspired itineraries and easy city escapes.
While many Washington, DC metro-area residents opt to spend their beach days in Ocean City, Maryland or one of the Delaware beaches like Rehoboth, Dewey or Bethany, travelers too often overlook Maryland’s Eastern Shore — a stunning summer spot flanking the Chesapeake Bay.
The Eastern Shore is quieter than Ocean City, with fewer family-friendly activities and more nautical and historic appeal best enjoyed by couples looking for a romantic escape.
Our favorite town is St. Michaels, where the history can be traced back to the 1600s. It became infamous during the War of 1812, when locals tricked the British by hanging lanterns just outside the city, causing the Brits to miss their target. While the Colonial charm is hard to miss, there is also plenty of modern shopping, quality dining and activities that range from visiting a rum distillery to sailing and kayaking.
Best of all, it’s a doable drive from a number of major East Coast cities: an hour-and-a-half from DC, two from Philadelphia and still reasonable three-and-a-half hours from New York City. (Keep a good card for earning points on gas purchases in your wallet, like the Citi ThankYou Premier Card. You’ll earn 3x points every time you fill up.)
Here are five ways to spend a long summer weekend in the Eastern Shore’s picturesque town of St. Michaels.
You can lounge at a luxurious resort
The Inn at Perry Cabin by Belmond is a historic property dating back to 1816 that was once owned by designer Laura Ashley and her husband, Sir Bernard Ashley. It was also the site of the main wedding reception in the movie “The Wedding Crashers.” Recently refreshed by renowned designer Alexandra Champalimaud (who also reimagined The Plaza and The Pierre in New York City), the inn features French doors that lead to private decks, patios or verandas and nautically-inspired details.
Sprawling across 25 lush waterfront acres, the hotel has six sailboats and yachts for guests to use. Book our personal favorite package, “Skip the Bridge” ($865), which picks up guests before the traffic-clogged Bay Bridge from Baltimore–Washington International Airport (BWI), or from the Annapolis or Baltimore train stations and ferries them to the Inn aboard their custom Hinckley yacht, Five Star.
Staff will greet you on board by sabering a bottle of Champagne, and you can complete your check in on the boat so, upon arrival at the Inn’s private dock, you can go straight to your room (a one-night stay is included in the package). Other amenities to take advantage of include the Inn’s kayaks and SUPs, the infinity pool and its adjacent bar, the brand new tennis courts and the just-opened 18-hole golf course, the Links at Perry Cabin.
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