Like Nantucket Reds, they'll never go out of style.
Galley Beach
Credit: Courtesy of Galley Beach

We’ve already briefed you on the most exciting new restaurants in Nantucket, but on this historic island, where many visitors return year after year, a great deal stays the same; and many classic restaurants are as good as they’ve ever been. Here’s a guide to the tried-and-true.

Special Occasions

Anniversary? Milestone birthday? Wedding proposal? Odds are, you’re going to Straight Wharf, Galley Beach, or Topper’s at The Wauwinet. These three Nantucket stalwarts, each one on the water, have been among the island’s special occasion restaurants for decades. (Just don’t expect to leave any one of them without dropping three figures a head.)

Opening directly onto Nantucket Harbor, Straight Wharf Restaurant (6 Harbor Square, 508-228-4499) is a perfect complement to the casual Cru across the way—more serene, more jackets and ties, and a different but a no less fabulous seafood-heavy menu. You’ll start off with the bluefish pate, a Nantucket staple; though everything’s enticing, it’s hard to pass up the Straight Wharf Clam Bake—buttered lobster with sweet corn, chorizo, potatoes, and littleneck clams. If you’re doing one decadent meal on Nantucket, this is an excellent choice.

As is Topper’s at The Wauwinet (120 Wauwinet Rd., 508-228-8768). Over on the other end of Nantucket Harbor—a 30-minute drive from town, which is about as far away as anything can be on this island—Topper’s sits within the Wauwinet Hotel, Nantucket's only member of Relais & Châteaux. And while you could grab a taxi out there, it’s far better to approach by boat. From town, it’s nearly an hour’s cruise across the water on the “Wauwinet Lady” (drinks served aboard, of course).

TOPPER's at The Wauwinet
Credit: Courtesy of Nantucket Island Resorts

Dinner at Topper’s is lavish, beautifully done and generally a three-course prix fixe. Gin-cured ocean trout or foie gras terrine to start, perhaps; butter-poached lobster or veal sirloin to follow? The wine list is extraordinary in its own right —more than 1450 bottles deep, and the multiple-time winner of the Wine Spectator Grand Award; and, just as importantly, has the sommeliers to guide you through.

Back closer to town, on Nantucket’s north shore, Galley Beach (54 Jefferson Ave., 508-228-9641) is a bit sceney, but indisputably beautiful—an open-air restaurant facing an expansive private beach and the glassy waters of the Nantucket Sound beyond. The menu is indulgent, with contemporary touches—modern takes on escargot and sweetbreads, scallops and filet mignon, all beautifully plated.

A Little Lower-Key

Looking for something a little less reminiscent of a resort? It’s true: Nantucket is a playground for the well-to-do. But it’s also a small, quirky New England town, which you’ll feel keenly at Le Languedoc (24 Broad St., 508-228-2552).

Le Languedoc
Credit: Wendy Mills

Beloved by locals and visitors alike. It’s a welcoming, bustling bistro, so popular the bar seats book out in advance; there are people who live on the island year-round with standing Sunday reservations more or less in perpetuity. Here, the culinary pleasures are simple and genuine: braised littleneck clams, the cheeseburger with garlic fries and the best steak frites on the island. It’s easy to come back week after week.

Then again, I’ve done ten-day vacations on Nantucket when I’ve eaten at Black-Eyed Susan’s (10 India St., 508-325-0308) three times in a row. Imagine a no-frills diner converted into a cozy modern restaurant—get a seat at the counter and watch your dinner fired right in front of you. There’s always a new international influence: this year, the exemplified with the “Pad Thai Pancake,” with Gulf shrimp, Napa cabbage slaw, peanuts, and a chili-tamarind syrup as well as the satay-spiced salmon over sticky rice “risotto” with Panang curry. The tuna tartar is never listed on the menu, but always a special: Get it. And take note: They’re BYOB, so pick up a great bottle at Epernay Wine and Spirits (1 N. Beach St., 508-228-2755) or Current Vintage (4 Easy St., 508-228-5073) on your way.

Brunch and Late Night

Black-Eyed Susan’s also does a fabulous breakfast—you can’t beat the sourdough French Toast with the orange-Jack Daniels butter, the corned beef hash, or the Portuguese scramble with linguica and tomatoes. Just get in line early; even slightly off-season or on a rainy Wednesday morning, it can be among the longest waits in town.

Black Eyed Susan's
Credit: Carey Jones

The Boarding House (12 Federal St., 508-228-9622), smack in the center of town on the corner of India and Federal, serves a nice dinner, but it’s best early and late. Early, for a deliciously civilized brunch—toss on a sundress or your Nantucket Reds; claim a table on the patio, with the best people-watching in town; and go to town on honey-almond French toast, avocado eggs Benedict, or fried soft-shell crabs—plus a bacon Bloody Mary. And late, when the front barroom becomes one of the rowdier all-ages parties in town. Whale’s Tales and vodka-cranberries for all.

And while the inimitable Club Car (1 Main St., 508-228-1101)is under new ownership this year, shedding its old-school menu of oysters Rockefeller and beef Wellington, the classic piano bar inside the train car is as lively as ever. If your idea of a nightcap is a Scotch and a “Piano Man” singalong, you’re still in good hands.

The Club Car
Credit: Matt Kisiday Photography