Your East Coast Summer Sorted

NANTUCKET, MA
WHAT Just 30 miles south of Cape Cod, the one-time whaling community attracts a steady swath of summering Brahmins, seasonal celebs, and day tourists seeking that quintessential gray-shingled New England backdrop. Book the hour-long fast ferry out of Hyannis or make like the monied and hop a 30-minute flight from Boston.

WEAR Thought Nantucket Red bermuda shorts were a myth? Stroll the cobblestoned Main Street and you’ll spot them en masse, along with whale belts, gold-buttoned blazers, and myriad popped collars. Hit up Murray’s Toggery Shop or Nobby Clothes Shop to emulate the look.

ORDER Start the day with blueberry pancakes at Black-Eyed Susan’s before moving on to a lunchtime lobster roll (Straight Wharf Fish Store and Blue Bellies Food Truck are two strong options). Event diners head to Topper’s Restaurant for an epic alfresco repast in front of the Nantucket Bay sunset. Make late-night merry at new hotspot Cru, an in-town oyster bar.

OVERHEAR Complaints about private jet fuel cost. Neighbors fretting about the beach erosion in Scionsonset (“Sconset”). The rumored whereabouts of Secretary of State John Kerry. Inadvertent stock tips from young banker types day-drinking at Cisco Brewery.

KENNEBUNKPORT, ME
WHAT Who knew the quintessential coastal Maine experience was less than a two-hour drive from Boston? The charming New England village  offers stunning water views, an artsy downtown and local watering holes that double as fine dining.

WEAR Refined rugged — think LL Bean mixed with Lily Pulitzer. Boat shoes and a striped pullover will take you far. Finish off any ensemble with a recycled-sail tote from in-town boutique Daytrip Society.

ORDER Slip over the bridge to Kennebunk for the award-winning lobster roll at The Clam Shack (tip: get it with mayo and butter). Recently opened hotel The Boathouse offers terrific new American dining from chef David Turin; reserve a table on the wraparound deck overlooking the harbor. End the evening drinking Sauv Blanc with locals at Old Vines Wine Bar.

OVERHEAR Analysis of ocean currents. Loud sports opinions at Federal Jack’s Brew Pub. “Where’s the Bush compound?” is a never-to-die tourist refrain. (For the record, it’s a few miles outside of town on Walker’s Point.)

MARTHA’S VINEYARD, MA
WHAT If it’s good enough for Meg Ryan, Carly Simon and President Obama, it’s good enough for the rest of us. The bucolic Massachusetts island beckons with unspoiled beaches, fine dining and a casually exclusive vibe. Just a 45-minute boat trip from Falmouth, the seaside escape is also accessible to Manhattanites via the five-hour Seastreak Ferry ride.

WEAR Tevas and forty-dollar T-shirts work well as an everyday uniform; hit up one of the island’s three Black Dog retail stores to get up to speed. To fight evening chill, a fleece is as good as a pashmina.

ORDER Queue up early for an apple fritter at Back Door Donuts. Lobster obsessives get their crustaceous fix at super-caz Larsen’s Fish Market in Menemsha. Savor locavore fare at State Road, then sample local brews at Offshore Ale in Oak Bluffs, one of the island’s few non-dry towns. Recover with a no-expense-spared Sunday brunch buffet at the Harbor View Hotel (Geraldo Rivera’s been spotted there).

OVERHEAR Kennedys referred to by their first name. Dissection of the president’s approval ratings. Celebrity real estate rumors. (“PLEASE don’t let Lady Gaga move here!”) Islander gossip from local fisherman at Dock Street Diner.

BLOCK ISLAND, RI
WHAT Thirteen miles off the coast of Rhode Island (and just 14 miles east of Montauk), Block Island is less sceney alternative to Nantucket or the Hamptons. Though the island does have a small airport, nearly everyone opts to arrive by ferry: During high season (Memorial Day through Labor Day), ferries depart every couple of hours from New London, CT, Newport and Point Judith, RI and Montauk, NY.

WEAR Laid-back prep. Think stone-washed sweatshirts bearing the island’s outline, pastel baseball hats and shoes sturdy enough for biking or moped-ing about town. Stock up at the boutiques along Water Street, like Star Department Store or Island Outfitters.

ORDER Start your morning at Old Post Office Bagel Shop (housed in — you guessed it — a former post office), lunch on lobster rolls at Finn’s or the Oar and do dinner at Dead Eye Dicks. Catch live music at Captain Nick’s and dance the night away at McGovern’s Yellow Kittens.

OVERHEAR Debate about the new watering hole in town, Poor People’s Pub, which dishes up solid bar grub and sets the scene for fierce cornhole competitions. Tip: head here over July 4th, when Ocean Avenue plays host to the island’s buzzing parade.

CAPE COD, MA
WHAT No two words encapsulate summertime escape better than “Cape Cod.” The Easternmost portion of Massachusetts breaks down into fifteen diverse towns offering sand-dune beaches, honky-tonk bars and arguably the country’s gay-friendliest enclave. Avoid migraine-inducing bridge traffic by hopping the 90-minute Boston-to-Provincetown ferry.

WEAR Unless you’re a lip-synching drag queen in P-town, the Cape is not a time for sexy. Stay simple with one-piece swimsuits, hooded sweatshirts, and light cotton dresses. Or blow your vacation budget entirely at the Marc Jacobs store on Commercial Street.

ORDER Nab fresh-from-the-oven fruit danishes at PB Boulangerie Bistro. Pause on the Rail Trail bike path for fried clams at the epically popular Arnold’s (reopening in mid-May). Find your shellfish nirvana at Abba, where the shrimp and lobster pad thai elicits pleas for the recipe. Embrace the nightlife with margaritas and live music at the Beachcomber.

OVERHEAR Heated debates over summertime reading assignments and whispered rumors about P-town’s new Kiehl’s store. Summering psychiatrists dissecting health care law at the Wellfleet kettle ponds.

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