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.

| Boston Magazine |

Photo by Carl Tremblay

Photo by Carl Tremblay


Island vet Charlie Graeber breaks down the mythic snobbery of the “faraway isle” and advises arrivistes on how to blend in. (Hint: Leave the “ACK” visor at home.)

I know, I know: Unless you’re one of us, you probably think Nantucket is a snobby, whale-pants sort of place. To which I say: Who invited you? I didn’t invite you.

I jest. In reality, this slander is only partially accurate. Anyway, one could argue that snobbery itself is as American as apple pie or school shootings; Nantucket, then, is just a mini America. On this 14-mile-long, swoosh-shaped glacial sand dump, native Algonquins have been supplemented by waves of Quakers, Cape Verdeans, Irish, Scots, Jamaicans, Brazilians, and Eastern Europeans (the current newbies hail, I think, from Ukraine and Ecuador). Just as on mainland America, each group has bought into the dream, then waited for the arrival of a new group to be snotty about.

It can take years to decode the subtle anthropological semaphore of island class and caste. Or, you can simply read the bumper stickers, a Nantucketer’s favorite soapbox. The ones that convey some version of “Go Home” are preferred by the true whaler-blood, pre-Seabee Nantucketers; you’ll find them plastered on the backs of 2009 SUVs paid for by the booming Nouveau Nantucketer economy and parked outside places like Faregrounds, a serviceable year-round beer-and-basics restaurant.

These year-round locals, in turn, are called “coofs” or “shoes” by the blue-haired, inherited-before-you Nantucketers who use “summer” as a verb. This breed buys its weekly Triscuits and kippered herring snacks at the Grand Union, née A&P, and daily gin at ‘Sconset Bookstore or Islander Package, and the only stickers on the bumpers of its woody Wagoneers are two decades’ worth of off-road driving permits.

Meanwhile, both these social groups stinkeye the new, endless-summering Palm Beach crowd, who have crashed the party with cash so green and teeth so white and mufti so damned Nantuckety that one can only conclude there must be a special “Nantuckety” section in the SkyMall catalog. Find them frequenting the Pearl or White Elephant, but look carefully: A proprietary “ACK” bumper sticker can be tough to spot on the massive flank of a snowbird Hummer.

No matter which circle you fall into—moneyed locals, non-native dishwashers, ill-behaved tourists—it’s easy to be a snob on Nantucket. Try rolling your eyes at the spawning throngs of weekending yarbos who pack the Gazebo in Hanes tanks dewy with Axe body spray and apple-tini dribble: Yes, you can! Or at the Young’s-scooter-riding mainlanders whom locals call “S.P.O.R.E.s” (“Stupid People On Rented Equipment”), because there’s nothing flattering about a cannonball helmet or a farting little two-stroke engine or, for that matter, quaking back fat. And, of course, one should be especially snotty about Nantucket snobs like myself—sometimes “summering,” sometimes scalloping, but always squatting in family houses we could never, ever afford at current prices.

Every summer on-island, it’s the same: People come from all over the planet, then try to fit in by “going preppy.” This is silly and wrong. Most end up looking like the pop-collared baddies in Revenge of the Nerds or Pretty in Pink. Don’t be those people. (And definitely don’t be one of those people who visit Nantucket just for the opportunity to buy something with the word “Nantucket” on it. I understand the excitement, but please: Be careful. I have personally witnessed a tourist, wearing a Nantucket hat, “ACK” sweatshirt, and Murray’s Nantucket Reds, taking a bite from a Pepperidge Farm Nantucket cookie. He then took a swig of Nantucket Nectars and literally traveled backward in time.)

To me, the “real” Nantucket isn’t fancy. Look, for example, at the old houses. Most (like my family’s), while neither large nor elaborate, are beautiful, if only in their simplicity. And like all beautiful things built near the Atlantic Ocean, they are also deteriorating pains in the ass. Many are painted the island’s unofficial color, Nantucket Red, which is now associated with wealth and privilege but stems from the salt-and-sea-faded surplus red government paint that was once used to cover pretty much every man-made surface here.

This, in essence, is my Nantucket: a rotting treasure, a melting snowflake, both souped up and falling apart. It is private yachts and public beaches, idle summer sun-worshippers and working winter scallopers. It is the $17 million summer homes and the winter nor’easters that wash them away. Ask anyone who actually lives here (and no, they are not reenactors): The island is both quaint and genuine. This fact hits home sometime around October, when the skies get big and the mercury sinks and this trophy of manicured hedges and gilded vessels reverts to a cold and shuttered speck at sea.

During the warmer months, the real value of Nantucket is access to that water. Unlike privatized Martha’s Vineyard (Stomp them Grapes! Go Whalers!), Nantucket is a 360-degree public beach, where everyone’s fun starts at the shoreline.

Example: fishing. Even if you don’t like to fish, you’ll definitely love pretending to. Pack a Something Natural picnic and a growler from Cisco Brewers and stab a surf-casting pole into Smith’s Point or any of the southern beaches—Cisco, “Fat Ladies,” even Surfside—past Bartlett’s Farm. In reality, most island fishing has less to do with fish than with friends. (Although, caveat: When the blues or stripers are running, you cannot help but catch one. I’ve watched a tuxedoed dude pull up surfside in a Jeep, toss a line, and—bam—reel in a thrashing keeper. The whole thing took 15 seconds. Both chef and dinner were gone before I could ask about the tux.)

In the protected harbor you can sail or windsurf or, if you have political aspirations, kiteboard. The island expands exponentially by boat—rent a kayak from Sea Nantucket on the Washington Street Extension and explore the uninhabited sandbar of Coatue. At the farthest reach of the harbor, you’ll find the dock of a rather posh hotel called the Wauwinet. And though hunting the world’s largest martini is not technically a water sport, it’s still worth mentioning, if only as a caution. The harbor is lousy with sandbars and sea monsters, especially when returning from said martini in, say, a borrowed dinghy steered by moonlight.

At sunset, libations at the RopeWalk’s back bar are a good capper to a hard day of boating, as is lining up for a BYOB seat at Black Eyed Susan’s. Flip-flops suit the Jetties’ casual beach fare, but you might fancy a blazer to enjoy Le Languedoc or the restaurants at the Club Car and Straight Wharf. No shirt, no shoes? No problem! You can always get service, not to mention a 3-pound lobster, on the porch of Sayle’s Seafood. Afterward, the Club Car train bar (which you might remember as the happy-hour spot on everyone’s favorite Nantucket-based sitcom, Wings…or not) has apéritifs and a surprisingly tolerable piano sing-along. Prep schoolers looking for love and rum—not in that order—crowd the bars of both Straight Wharf and Cap’n Tobey’s, while the gin ‘n’ cigar contingent heads to 21 Federal or the Boarding House.

But all that super-silly superciliousness is checked at the door of the Chicken Box, where carpenters and bridesmaids and yachtsmen, Palm Beachers and Cape Verdeans, and the old, the young, and the ageless pack in together to cheer a beery jam band (or the Wailers, or Little Feat). The Chicken Box isn’t much, but everyone eventually ends up there…. And in that spirit, bartender-turned-co-owner John Jordin promises he’ll knock a few bucks off the cover charge for anyone who mentions this tip sheet along with my name. Because on a snobby little island like Nantucket, it’s all about who you know.



Get There

The Steamship Authority, with five daily high-speed, one-hour trips ($32.50 one way), offers the attraction of easy Cape-side parking. 508-477-8600, Cape Air runs 14 daily flights from Logan ($234 roundtrip); better yet, drive to Hyannis for an Island Airlines $102 roundtrip. 508-771-6944,; 508-228-7575, You can also charter Ocean Wings Air planes for upward of $1,450 one way. Be sure to book well in advance, though, as Nantucket’s airport sees more than 40,000 flights per summer. 508-325-5548,


Hotel Green: Woman-about-town Vanessa Noel—that’s her high-end shoe store you’ll see next door—used only eco-friendly paints and décor in remodeling this modern, centrally located hotel. Doubles from $250, 5 Chestnut St., 508-228-5300,

Nantucket Whaler: Affable owners Randi and Calli—who may doublehandedly debunk the “stuffy Nantucket” myth—make a stay here feel more like a visit. Doubles from $325, 8 N. Water St., 508-228-6597,

The Summer House: Couples both romantic and frugal should try the India Street address for secret summer deals, and the ‘Sconset branch for its heated pool. 31 India St. and 17 Ocean Ave., 508-257-4577,

The Wauwinet: This spot epitomizes outsiders’ preconceptions with a Four Seasons–esque feel meshed with shabby-chic décor, fine dining, and extravagant spa pampering. Doubles from $700, 120 Wauwinet Rd., 508-228-0145,

Eat and Drink

Boarding House: Wine director Jamie Nickerson’s “red, white, and green” attitude translates into an array of biodynamic vintages. Not that the after-dinner crowd cares—they’re just there to sip and be seen. 12 Federal St., 508-228-9622,

The Chicken Box: Original owner Willie House left his job as a family servant to sell fried chicken from a remodeled shack. Some 50 years later, the bar is the great Nantucket equalizer for tipplers of all (legal) ages. 16 Dave St., 508-228-9717,

Company of the Cauldron: Each week All and Andrea Kovalencik post a fresh prix fixe menu outside their one-room, ivy-covered dinner party–cum–very intimate restaurant. 5 India St., 508-228-4016,

The Downy Flake: If the parking lot full of pickups doesn’t tip you off, the hearty breakfast (homemade doughnuts!) will: This place is local, through and through. 18 Sparks Ave., 508-228-4533.

Straight Wharf: Boston transplants Gabriel Frasca and Amanda Lydon transformed this into the island’s finest eatery. Note: Finest does not mean stuffiest; ask to sit on the back deck. 6 Harbor Sq., 508-228-4499, straight


Bartlett’s Farm: Nantucket’s largest family farm sells fruit, organic foods, and prepared meals. 33 Bartlett Farm Rd., 508-228-9403,

Cisco Brewers: Randy Hudson turned a hippie dream into a hoppy utopia complete with a Sonoma-style outdoor tasting bar. Pick up a recyclable, refillable growler bottle, and keep your beer fresh and local. 5 Bartlett Farm Rd., 508-325-5929,

Murray’s Toggery Shop: The savvy owner made millions—and many color-coordinated outfits—when he created the iconic Nantucket Reds pants now worn by upper-crusters worldwide. 62 Main St., 508-228-0437,

Nantucket Bookworks: Your kooky old aunt would feel right at home amid the boxing nun and Mexican Day of the Dead doodads; oh, and books by islanders like David Halberstam, Russell Banks, and Ned Rorem. 25 Broad St., 508-228-4000,


Cisco Beach: The surfer-friendly spot attracts legions of weekend crowds; beware the occasional strong undertow.

Ram Pasture: Modern-day Robinson Crusoes can walk or bike through protected Ram Pasture to pop out onto an inviting expanse of untrampled sand.

Surfside Beach: The busy beach hosts a seemingly endless string of summer picnics and is well maintained with lifeguards, showers, and a shuttle into town. All beaches, 508-228-0925,


Bette Spriggs: Fork over $75 and the venerable, straw-hatted Mrs. Spriggs will tie your knot, often with vows rich in connubial wisdom gleaned from her 36-year marriage to former Nantucket selectman Frank Spriggs. 508-228-4819.

James Michael Merberg: Should you accidentally get overserved (and busted on the Jeep ride home), call the noted attorney—he’s defended everyone from tourists to the local sheriff. 617-723-1990.

John Logan: Forgo the spas and buzz certified massage therapist John “Fingers” Logan, who specializes in Thai techniques and makes house calls. Bonus hookup: Logan runs a scallop boat in the off-season. 508-228-1296.

Spanky: The one-named wonder remains the best “clam guy” in town. 508-228-9898.


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,

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