The Islands, Decoded

Whether you're a first-time weekender or have a lifetime of summers under your whale belt, our discriminating guide to navigating Martha's Vineyard and Nantucket like a veteran will guarantee nobody will know the difference.

Martha’s Vineyard

The Taylors, the Gyllenhaals, and Billary aside, writer and erstwhile vineyard local Jason Gay discovers the island hasn’t been totally overrun with glitz and glamour.

More than 10 years ago, while working as a reporter for the Vineyard Gazette, I had the pleasure of “covering” the wedding of Ted Danson and Mary Steenburgen. Bill Clinton was there, back when he was a likable president. Tom Hanks was there, back when he was a likable movie star. Also in attendance were James Taylor, Kirstie Alley, Woody Harrelson, and Jeff Goldblum. I know: Jeff Goldblum?

I heard it was a pretty fun time. But I never saw a slice of cake, a drunken uncle, an awkward toast, or Jeff Goldblum doing the chicken dance. That’s because I was standing at the edge of the Danson-Steenburgen driveway, shivering in the damp autumn cold with a bunch of other media slobs. We weren’t invited; we weren’t even allowed inside.

The next morning, my fellow reporters couldn’t stop mocking my stakeout.

“You mean you stood at the end of the driveway the whole night?” one asked.


“How long?”

“I don’t know,” I said. “Four hours. Maybe five.”

“You’re an idiot.”

Ever since Jimmy Cagney repaired to his homestead on North Road to be a gentleman farmer, Martha’s Vineyard has been a place where celebrities come to be ignored. No one cared—or they pretended not to care, at least—when John Belushi pounded the drums at the Hot Tin Roof nightclub, when Spike Lee strolled Oak Bluffs’ Circuit Avenue in his Air Jordans, or when Jackie O swanned among the Philip Craig mysteries at the Bunch of Grapes Bookstore in Vineyard Haven. The isle prided itself, maybe a little too much, on its blasé attitude toward fame; anything else was simply tawdry. When the Gazette devoted a series to Mike Nichols and Diane Sawyer’s new $5.3 million house (then an island record) in the mid-’90s, readers complained it was invasive, and an irritated Nichols wrote in to say if the coverage didn’t stop, he’d turn his beachfront home into a Taco Bell.

The subsequent arrival of Bubba and Hillary, star-effers nonpareil, was poised to send the Vineyard into an intractable fame spiral. It’s true the senior generation of celebrities (Mike Wallace, the late Beverly Sills) has lately been joined by glitzier visitors (Jay-Z and Beyoncé, Meg Ryan, Reese Witherspoon and Jake Gyllenhaal), and as the island’s profile rises, old-timers are decrying the Vineyard’s “Hamptonization.” Hummers sometimes stink up the parking lot of the Chilmark Store. That $5.3 million Nichols spent on his house now seems paltry; in 2006, a European couple paid $25 million for an Edgartown oceanfront spread.

But don’t let the whiners fool you. Despite all the recent celebrity haze, tabloid BS, and pricey lifestyle accoutrements (pools, tennis courts, private chefs), the Vineyard hasn’t really changed. Sure, there are differences: The new ferries are fancier and WiFi-enabled; the drab old Tisbury Inn burned down and has been replaced by the Mansion House, a glossy Victorian-style number; the so-bad-it-was-great Atlantic Connection is now a lame-o video arcade. The Hot Tin Roof is defunct, and Art Buchwald, the resident jester who raised millions for local charities, passed away last year.

What remains is what distinguished the Vineyard from other islands 10 and 25 and 50 years ago: an unrelenting beauty complemented by the laid-back nature of its residents. The finest beaches—including Lucy Vincent, Gay Head, and Lambert’s Cove—are still unspoiled. The fish shacks in Menemsha are relics of another era, and people still salute the sunsets on that town’s beach with nightly applause. The dress code, best expressed through the racks at Murray’s or local chain Island Outfitters, stays rumpled, cotton, and sockless. Social snobbery exists, but the Vineyard isn’t a place you go to get ahead in the world. If you want that kind of crap, take your whale belt to Nantucket.

In the end, it’s consistency, not celebrity, that makes the Vineyard great. True, so-called hot spots open all the time (I hear Edgartown’s spaetzle-serving restaurant Détente is a favorite of Dunkin’ Donuts mouthpiece Rachael Ray, and that at nearby Atria, the patio is packed nightly), yet it’s comforting to know that every summer, the finest fried clams in the universe can still be found at rickety Menemsha clam shack the Bite. And that the best place to lazily watch a day pass is the porch bench at Alley’s General Store in West Tisbury. And that the coolest spot to stay is still a rambling countryside farm called the Captain Flanders House. And for a drink amid friendly locals, it’s always the Ritz Café on Circuit Avenue.

Just remember to take pleasure in knowing you could have experienced all these things long before Bill Clinton showed up on the Vineyard. Jeff Goldblum, too.



Get There

The Steamship Authority is your best bet, with 14 daily 45-minute Woods Hole–Vineyard ferries ($7.50 one way). 508-477-8600, Or consider the Island Queen: It’s cheap ($8), fast (35 minutes), and friendly. (True story: The captain once held the ship for us.) 508-548-4800, If you can stomach a 10-seater, you can be oceanside in under an hour via one of Cape Air’s daily flights from Logan ($234 roundtrip). Take the 10 a.m., usually the least crowded. 508-771-6944, Or go the catered route and book a charter from Blue Star Jets, starting at $1,000 per hour. 866-538-8463,


Captain R. Flanders House: Far from Edgartown’s fanny-packing day-trippers, the 1700s farmhouse is all secluded privacy. Bonus: Jackie O’s old house, er, compound is nearby. Doubles from $175, North Road, Chilmark, 508-645-3123,

Harbor View Hotel & Resort: Just reopened after a $77 million facelift, the grand dame of Vineyard resorts hosts posh families (and the occasional bridezilla). Doubles from $375, 131 N. Water St., Edgartown, 508-627-7000,

Mansion House: The former Tisbury Inn got a much-needed makeover that added a spa and fitness center and banished all things doily. Doubles from $279, 9 Main St., Vineyard Haven, 508-693-2200,

Winnetu Oceanside Resort: The faded-luxury-style Winnetu beckons to harried urban toilers. Eleven acres of lawn and sandy beach, plus yoga workouts, ensure respite. Doubles from $230, 31 Dunes Rd., Edgartown, 508-310-1733,

Eat and Drink

Atria: Playful menu items like Pig Pig Pig and Cod Is Great, Cod Is Good save this white-tablecloth eatery from stuffiness. Ask to sit on the patio—the waitstaff keeps bug spray behind the bar. 137 Main St., Edgartown, 508-627-5850,

The Bite: This roadside shack is the ideal spot for loading up on crispy fried seafood to nibble while taking in the Menemsha sunset. 29 Basin Rd., Menemsha, 508-645-9239,

Détente: Only 12 items make the menu each night; fortunately, all are typically fantastic (as is the sinful Nutella pot de crème). Nevin Square, Edgartown, 508-627-8810,

Ritz Café: This straightforward watering hole—known for rowdy local crowds—is the island’s anti-snobbery stronghold. One Circuit A
ve., Oak Bluffs, 508-693-9851.


Alley’s General Store: The Vineyard’s oldest pantry is a good place to people-watch for both weathered locals and burnished celebs. State Road, West Tisbury, 508-693-0088.

Bunch of Grapes Bookstore: Local author William Styron dubbed it “the best bookstore in America,” and we’re not arguing. 44 Main St., Vineyard Haven, 508-693-2291,

Chilmark Store: Another A-list haunt, the no-frills provisioner serves fresh salads and sandwiches. Snag a perch on the porch. 7 State Rd., Chilmark, 508-645-3655.

Island Outfitters: Prepsters and surf dudes alike buy their Reef flip-flops and Costa Del Mar shades at the long-standing island chain. One Post Office Sq., Oak Bluffs, 508-693-5003,


Gay Head (Moshup Beach): A short hike from the parking lot delivers sun lovers—and some determined nudists—to a swath of soft white sand and a view of the 200-foot-tall Aquinnah Cliffs. Off Moshup Trail, Aquinnah, 508-693-0085,

Katama Beach (South Beach): Everyone from Michael Jordan to hordes of summering coeds (and the lifeguards who love them) lay down towels on this 3-mile barrier beach that has rare ample parking. End of Katama Road, Edgartown, 508-627-6145.

Lambert’s Cove: Okay, it’s technically residents-only, but scoring a pass isn’t so hard: Rent a house in the area or hop a ride with a local friend. Or (shhh!) park elsewhere and try to walk on. The views of Vineyard Sound and the Elizabeth Islands are worth it. Lambert’s Cove Road, West Tisbury, 508-696-0147,

Lucy Vincent Beach: Another residents-only policy means hoi polloi are scarce and unspoiled vistas abundant. Tip: Some up-island hotels, like the Beach Plum Inn, provide guests a gratis pass. South Road, Chilmark, 508-645-2100,


Zebee Voss: The in-demand masseuse vows never to “fluff and buff,” and we believe her. Our last treatment left us sore (bruised?) but, a day later, completely at peace. An Island Touch, 110 State Rd., Vineyard Haven, 508-693-0300,

Tom Osmers: The West Tisbury shellfish constable and oyster fisherman knows more about island seafood than anyone else. See him for fresh cod, clams, and scallops, among other ocean delicacies. 508-696-8277.

Bouclé Salon and Spa: Beauty emergency? Bouclé excels at blowouts, mani-pedis, and last-minute facials. Its staff is young; its décor is cute but not cloying. 12 N. Water St., Edgartown, 508-627-3853,