Photo by Jaime Martorano. At the far eastern tip of Long Island, Montauk is the kind of laid-back beach town summer was made for.
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Surfers and paddle boarders take to the waves at Ditch Plains, while bird watchers look skyward at Hither Hills State Park. Later, dine on local lobster and Point Judith calamari by candlelight at the 17th-century White Horse Tavern. With its colorful Victorian homes and all-American charm, Cape May feels like a journey back in time.
If the heat gets the better of you, a drink on the veranda of the Virginia Hotel is sure to revive you. For an understated alternative to the spectacle that overtakes the Hamptons each weekend, in-the-know New Yorkers board the ferry to Shelter Island, a tranquil spit of land along in the Peconic River sandwiched between Long Island's North and South Forks.
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Drop your bags at The Chequita refurbished hotel with pastel-hued rooms that serve as a quiet backdrop to your romantic getaway. More ambitious types might choose to hike through the tidal creeks, freshwater marshes, and oak forests of Mashomack Reserve, or ply the calm seas by kayak or sailing class. Annapolis is often overshadowed by Baltimore, its neighbor to the north, but this postcard-perfect port town is a worth a visit in its own right. Naval Academy.
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Their 36 homemade flavors are rotated daily, so multiple visits are encouraged. JS Tip: Sit on the left side for the best view. Bed down at Brentwood Hotela revamped room motor lodge in Saratoga Springs that feels like a Brooklyn transplant thanks to its moody walls, brass fixtures, and Instagram-worthy bar. In the morning, drive 30 minutes north and rent a boat to explore the pristine shores of Lake George, the onetime summer playground of elite New York families like the Roosevelts and the Whitneys.
The deckhands will help you tie up on the dock at The Algonquinwhere you can enjoy a lunch of fish tacos and a shrimp-garnished Bloody Mary.
Then make your way to The Sagamorea white clapboard Gilded Age hotel that occupies its own island nearby. The resort can arrange everything from kayaking on a acre private lake to horseback riding along the forest trails. Things you buy may earn us a commission.
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