This East Coast Getaway Is the Perfect Alternative to The Hamptons

While it’s customary for many New York City dwellers to trek to the scenic town of East Hampton or the shores of Montauk for summer weekends, the dream of a refreshing alternative to The Hamptons madness constantly remains. Enter the town of St. Michaels in Maryland along the Chesapeake Bay, where lazy days filled with sailing, seafood, and antique shopping are just a train ride away.

Getting There

From Penn Station, New Yorkers can hop on a 2.5 hour train ride that takes you straight into Baltimore, where you can then make your way via a 1.5 hour drive to St. Michaels. Washington D.C. and Philadelphia natives are also in luck, with the town just a short 2-2.5 hour car ride away.

Where to Stay

The Inn at Perry Cabin is a colonial estate set right against the Miles River and feels like a home away from homes thanks to the the serenity of the Eastern Shore. With sprawling lawns, vibrant hydrangeas everywhere you look, and the ebb and flow of sailboats adding to your skyline view, you’ll be charmed right from the start.

Another highlight of shacking up at this waterfront locale is the option to “skip the bridge” post-train ride. The Inn offers boat rides from Baltimore straight to the property aboard their Hinckley yacht. As you skip traffic and sip champagne, you’ll arrive via boat to your magical weekend destination. It’s hard to imagine traveling any other way.

What to Do

From sailing to oyster foraging, there’s no shortage of activities at your disposal. The recently-opened Tennis Club by Cliff Drysdale and Links at Perry Cabin by Pete Dye showcase the region’s top-tier sports clubs. Whether you choose to play 18 holes against the breathtaking Chesapeake Bay backdrop or hit one of the tennis courts for a pickup game or lesson, you’ll have no problem staying active upon arrival.

Craving something more relaxing? At the Inn at Perry Cabin, visit the Linden Spa and adjacent pool for a day of decompression. Choose from an array of herbal massages and rejuvenating facials, or simply post up in a lounge chair with a summer read and cocktail.

For those in search of a nautical adventure, the Chesapeake Bay is at your disposal. The Inn offers guests an array of elegant yachts, from sightseeing on a chartered excursion to oyster foraging for an apéritif delight or dining along the water. You can also learn how to sail with a two-day class that requires no prior experience and teaches you the basics to confidently hit the waters. Post-boating, history buffs can visit the Chesapeake Bay Maritime Museum for tours and exhibitions on the rich past of the seafaring town.

Town Highlights

A trip down Talbot Street offers antique shopping, seafood bites and a local’s look inside the charming setting of St. Michaels. As you walk along the cobblestone streets showcasing structures that date back to the mid-1600’s, you can’t help but feel transported to times of the past.

For eats along the way, stop at one of the many old-school ice cream shops like Justine’s Ice Cream Parlour and JoJo’s Cupcakes & Cream, or pop into Blue Heron Coffee for a cold brew concoction unlike anything you’ve ever tasted. Agave Arts & Juicing Co. offers the unexpected coupling of cold-pressed juices and handmade jewelry, the perfect memento to commemorate your stay. For heartier options, testing your palette with fresh seafood from the bay is a must. 208 Talbot offers pan-seared crab cakes and scallops in a romantic setting, while The Crab Claw serves up classics in a more laid-back fashion. Bistro St. Michaels and Limoncello Wine Bar are also highlights if you need a moment away from the cuisine of the sea.

Can’t Leave Home Without

A breezy dress in nautical colors, espadrilles and chic sunnies take you from touring the town to dinner along the water. Top off your weekend essentials with a bathing suit in a bright gingham print and a straw bag for toting all your summer essentials.

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