New England Island Love Affairs: Martha’s Vineyard and Nantucket

Nantucket’s Summer House offers cottages and beachside dining.

When people talk about a luxurious New England summer getaway, there seem to be two categories: Martha’s Vineyard and Nantucket and everything else. The secluded Massachusetts islands — nestled just south of Cape Cod in the Atlantic — have long been known as intimate havens. You don’t just visit these islands, you become members of their tight-knit communities for the length of your stay. They are attractions without gimmicks, crowds or frills: there are no big malls, no towering music venues, no amusement parks or other kitschy tourist traps. They are simply the most comfortable, well-maintained and genuine areas to rusticate and soak in the deliriously pleasant calm of summer. Nothing much changes, as proponents like to say, but people keep coming back.

This isn’t to say you will have trouble finding something to do on either island. Throughout the summer, both have their share of wine, food and art festivals, boutique shopping, history and culture. But they are also home to some of the region’s most beautiful bike rides, sailing opportunities and sprawling, uncrowded shorelines. This is where you take your family to experience life together, to cook at home or eat at a small world-class restaurant, sip wine as the sun goes down on the west end of the island, and wake up early to see it rise on the east end. And it’s easy to get across the islands: Martha’s Vineyard is about 20 miles long from tip to tip (and 87 square miles in its entirety), and Nantucket is only 14 (less than 50 square miles). Here’s a taste of what each has to offer.

Martha’s Vineyard

Martha’s Vineyard is comprised of a few rural towns: Aquinnah, Chilmark, West Tisbury, and the more populous towns of Edgartown, Oak Bluffs and Vineyard Haven. Whether you’re looking for the natural beauties of pristine beaches, clay cliffs and bird watching, historical and cultural attractions, exquisite dining, an array of outdoor activities or the many artists, handcrafts and boutiques, “The Vineyard” has it all.

Festivals and Markets

If shopping for rare finds are your druthers, a great place to start is the Chilmark Flea Market, hosted by the Chilmark Community Church every summer from late June through early September. The oldest outdoor venue on the island, the market has evolved into a quirky shopper’s heaven. Quality hand-made items from antique sellers, artists, glassblowers, and jewelers mingle among imports, fine china and more—and many of the craftsmen are waiting on their folding chairs and in the backs of their trucks to speak with you. In what will be this market’s 45th year, the Flea, as it’s called among locals and returning visitors, holds within its lively stalls everything from vintage clothing and wire statues to mounted animal heads and stained glass windows.

At the Summer Vineyard Artisans Festival, the Historic Grange Hall in West Tisbury opens for a weekly juried art show and fair. You can meet with more than 70 artisans, from weavers, potters and quilters, to jewelers, painters and furniture makers, many of whom hold demonstrations.

The Featherstone Center for the Arts hosts a Flea and Arts Market throughout the summer, offering great selections for those on the island’s south side, along with classes, summer camps for children and events. This summer, camps range from painting and photography to silkscreen and printmaking. Special events include garden tea parties, the Featherstone’s annual gala, the third annual Potter’s Bowl and the Art of Chocolate Festival.

While on the topic of festivals, the OB Harbor Festival at Oaks Bluff on June 16 brings together over local and national 40 vendors for one of the island’s most popular events. Local artists, craftsmen and antique dealers, as well as non-profit organizations offering a tempting array of baked goods, raffles and information about their causes, will be on hand. Live music on the deck at Nancy’s featuring Martha’s Vineyard’s favorite bands, and the Midsummer Faerie Festival will entertain all ages with mystical storytelling and Celtic musicians. As always, an abundance of native seafood and gourmet treats await the festive gathering at this year’s Harbor Festival.

Boating and Beaching

Perhaps you’re more of the seagoing sort. Well, you’re still in luck. Martha’s Vineyard has some of the most intimate and beautiful oceanic activities around. Moonrise Kayak, for instance, shows you Martha’s Vineyard in a whole new light: moonlight. In celebration of the full moons of summer, Moonrise Kayak takes you nighttime tours of the coast. With a guide, you will kayak out as the sun sets and the moon rises, absorbing the wonder and romance of the region.

Kayak Quest lets you enjoy the Vineyard’s Sengekontacket Pond at your own pace on a self-guided tour, taking you on a journey with a series of clues to help you uncover the story of the pond’s people, places and wildlife. Your quest ends after you find the hidden quest box. Good luck!

Boat charters are also a popular island activity. Take a joyride for the afternoon or set sail to explore the New England coast—either way, there is an endless selection of friendly and experienced guides ready to take you out on the waters.


More than just a sister island to Martha’s Vineyard, Nantucket is a premier destination in its own right. “The Gray Lady,” one of the island’s nicknames, was once wealthy with the profits from the whaling industry; it is rich again with luxury real estate and outsiders from New York, D.C. and elsewhere. There are more intimate leisure activities than you could think about doing—golfing, tennis, kayaking, bird watching, fishing, historic architecture, museums, art galleries and events—and enough space to get away with doing nothing at all, if that suits you best. First of all, it holds within its small borders a web of gorgeous—and flat—biking paths. As the island is only 14 miles long by 3.5 miles wide, a cyclist can bike around the entire island in a day, while stopping along the way to enjoy the scenery, culture and cuisine.

D.C.’s connection to the two islands is legendary, whether you are mentioning the Laythams, the Rubensteins or many others. During the summer, one just might bump into someone from the D.C. neighborhood. On Nantucket’s east side, Siasconset, the Summer Home with its cottages, houses and Beachside Bistro boasts the best oceanfront weddings. One of its other restaurants is by chef Todd English, Figs at 29 Fair, near Main Street. Locally, we have the likes of Smith Point, Jettie’s and Surfside restaurants from Bo Blair, who named them after spots in Nantucket.


Nantucket is a small-time fisherman’s mecca. Its coast is home to the entire array of famous New England seafood delicacies—all of which are also available cooked and ready to eat at any of the first-class restaurants on the island. From striped bass and blue fish, to mussels, scallops, oysters and blue claw crabs, you could catch enough to make an enviable clam chowder, bouillabaisse, or just host an old fashioned clambake for your new neighbors. Just make sure to check with the Nantucket’s Marine and Coastal Resources Department for information on potential fishing restrictions.

Not Your Average Library

While a public library might not seem like the most exciting place to visit on your summer vacation, the Nantucket Atheneum is not your average library. This unique library plays a vital role in the community, providing a wide variety of cultural and educational services and events, as well as a fine picking of books, videos and audiobooks.

Among many events this summer, the Atheneum will be hosting a dance festival (July 24 – 28), featuring stars from the dance world brought together by artistic director Benjamin Millepied, a noted choreographer and former New York City Ballet principal dancer. The festival includes many free outreach events for adults and children and culminates with two evening performances on July 27 and July 28, which feature a dance program of classical and contemporary ballet.

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