Where to…

A quick guide to the popular spots where Greenwich goes to summer

1. MARTHA’S VINEYARD

“The Vineyard” is New England’s largest island with plenty to do—from exploring miles of beaches to taking a spin on America’s oldest working carousel. Being bored on the Vineyard isn’t an option.

Hit the surf
Locals agree that Aquinnah Public Beach (Moshup Beach) is the best spot to catch a wave. They advise arriving early to get parking and beware that although it’s illegal, nudists gravitate to this beach.

Watch the sunset
It’s a vigorous climb to the Edgartown Lighthouse, but a $5 fee will earn you the best view in Edgartown.

Sip a cocktail
Enjoy a Lookout Rum Punch at the beloved Lookout Tavern. This Vineyard staple sits high on a bluff and has sweeping views of the waterfront.

Build a sandcastle
Small waves, low dunes and lots of seashells make Joseph Sylvia State Beach popular with families. The beach runs between Oak Bluffs and Edgartown and is called “Bend-in-the-Road Beach.”

Steal a kiss
Grab the brass ring and sneak a smooch on the Flying Horses Carousel. It’s the nation’s oldest platform carousel and has been designated a national landmark.

Shop for souvenirs
Midnight Farm is the indie-chic boutique owned by Carly Simon. The eclectic and high-end goods draw celebs and locals alike.



2. THE HAMPTONS

If the Hamptons conjure images of over-the-top mansions and red-hot sports cars, you’re only half right. There is so much more to this stretch of beach towns at the eastern end of Long Island.

Hit the surf
Locals in Southampton swear by Meadow Lane, Road G; it’s where all the surfers hang out. They even have surf lessons and surf camps (try Flying Point Surf Camp). Looking for a spot in Montauk? Ditch Plains is a tried-and-true surfer destination.

Watch the sunset
Described as a dive bar with a jukebox, Montauket has the unlikely distinction of also offering the best sunset view in Montauk. Or go upscale in Sag Harbor and score a waterfront table at Bell and Anchor; the sunset is a nice accompaniment to the lobster and raw bar.

Build a sandcastle
Head to Mecox Beach Jobs Lane, Bridgehampton. For those who have yet to land a Bridgehampton Racquet & Surf Club membership, a $15 parking fee will buy you and your kids all necessary amenities for a day at the Mecox just next door.

Steal a kiss
The Parrish Art Museum occupies an unlikely setting more akin to a farm stand, but inside visitors enjoy world class contemporary art. Steal a kiss and post it on social media; unlike many museums, photography is allowed.

Shop for souvenirs
AERIN at 83 Main Street in Southampton is owned by Aerin Lauder, who has been coming to the Hamptons since she was a little girl. Her personally curated collection ranges from sandals to jewelry to unique objects for the home.

The 31 foot Friendship Sloop "Endeavor",  sailing off the coast of Nantucket,  provides excursion sailings to a group of visitors to this tranquil island
The 31 foot Friendship Sloop “Endeavor”, sailing off the coast of Nantucket, provides excursion sailings to a group of visitors to this tranquil island

3. NANTUCKET

Whether you arrive by ferry or flight, the inviting little island of Nantucket feels a world away. Now a getaway for the rich and famous, this former whaling town still retains the authenticity that made it the setting for Moby-Dick.

Hit the surf
Beginners can take lessons at Cisco Beach with Nantucket Island Surf School. Hanging ten not your thing? Try the less- exhausting stand-up paddleboarding.

Watch the sunset
Whether you hit Galley Beach restaurant and bar for dinner or drinks, be sure to stay for the sunset. Reserve a couch and tuck your toes into the sand as you watch the sun slip into the horizon. Try the Seaside martini, made with Hendrick’s gin and cucumber.

Sip a cocktail
No need to wait for sundown to enjoy a cocktail. Head out to Cru located at the end of Straight Wharf for a midday Bloody Mary. Or to Jettie’s Beach Bar for oysters and a cold beer.

Steal a kiss
Bonfires are technically illegal but seem to be commonplace. Kisses are best stolen with some heat and s’mores on the side.

Build a sandcastle
Though Children’s Beach sounds like the perfect spot for a sandcastle, locals recommend Jettie’s Beach, which also has gentle waves and a playground but features more space, oh, and cocktails.

Buy a souvenir
Nothing says “Nantucket” like an authentic pair of Nantucket Reds. Take home a pair of the iconic pinkish chinos from Murray’s Toggery Shop on Main Street.

Southeast Lighthouse on Block Island, Rhode Island, at sunrise.

Southeast Lighthouse on Block Island, Rhode Island, at sunrise.


4. BLOCK ISLAND

Just twelve miles off the coast of Rhode Island, you’ll find the tiny and utterly charming Block Island. Described by The Nature Conservancy as “one of the last twelve great places in the Western Hemisphere,” this pint-sized retreat packs a huge punch with 200-foot cliffs and miles of unspoiled beaches.

Hit the surf
Beginners head to the first section of Crescent Beach, a three-mile beach that offers up gentle waves. Serious surfers head to Mohegan Bluffs and Black Rock Beach; beware that access and surf conditions can be perilous.

Watch the sunset
Pack up your lawn chair and wine and get ready for a rare sunset view on the East Coast—one where the sun dips true west into the ocean. Head down Dories Cove Road to find a private spot on the beautiful beach tucked away in a cove.

Sip a cocktail
Enjoy a cold one on the wraparound veranda at the historic Atlantic Inn. From your wicker chair, you can enjoy breathtaking views of Old Harbor and the ocean beyond. Kids in tow? Try the neighboring Manisses Inn; while you enjoy the blackberry martini made with native blackberry puree, the kids can check out the exotic farm animals at Justin’s Farm and Garden (think fainting goats and yaks).

Steal a kiss
Head to Sandy Neck, the northernmost tip of the island where the two ocean currents meet. On a clear day you can see the Connecticut and Rhode Island coastlines, and even catch a glimpse of the Newport Bridge, plus lots of beautiful boat traffic.

Build a sandcastle
The three public beaches that comprise Crescent Beach make up a long, wonderful strip of public shoreline that is filled with families, but never as crowded as beaches on the mainland. Pack the sand toys and enjoy views of town and the cliffs.

Shop for a souvenir
Pop in to Block Island Trading Company to take home a unique treasure, from a bracelet engraved with the island’s coordinates to cocktail glasses etched with the island map. Can’t get there? It has the only year-round online gift shop.

Photographs: istock/OLEAGALBINSKY, KENNETH WIDEMANN, DIANE39

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