The 2023 Guide to Dining on Nantucket and Martha’s Vineyard

MARTHA’S VINEYARD

The Obama-anointed special occasion restaurant in Oak Bluffs is spread across an intimate indoor dining room and a tented, heated patio that’s a witness to live jazz each Thursday night. Every night, however, may be accompanied by local scallop crudo, housemade squid ink tagliatelle, and skate wing with fava beans and fiddleheads.

Alchemy, a 20-year veteran of the Edgartown dining scene situated in a historic, two-story home in the vacation town’s main street, continues to deliver with indulgent bistro classics including Jonah crab and grilled asparagus salad or a surf and turf plate that pairs filet medallions to butter-poached lobster with roasted garlic potatoes and truffle jus. And that’s not even mentioning the long-running establishment’s cocktail program, which can refresh with a French Quarter (vodka, St. Germain, grapefruit, bitters) or close out on a boozy Edgartown old fashioned, accented with housemade apple cider bitters.

The first thing you may want to know about Chilmark Tavern is that it is BYOB — a vital concern, as it is situated on the Vineyard’s last remaining dry town. Once you’ve digested that information, turn your attention to the roadside restaurant’s rustic menu, which includes such dishes as burrata with roasted peaches and local tomatoes, beer-battered fish and chips with malt vinegar dust, and porcini-rubbed New York strip steak.

Détente is a French word that refers to the easing of hostilities. But in Edgartown, it also refers to a husband-and-wife-owned restaurant that’s dabbled in housemade pastas and locally sourced ingredients since 2005. Whether seated indoors, at the restaurant’s garden-style patio or bellying up to its soapstone bar, you’ll be rewarded with heirloom tomato panzanella, slow-roasted Berkshire pork Bolognese or roasted quail with spaetzle and duck confit.

Some restaurants make you guess about their offerings: Salvatore’s Ristorante Italiano is not one of them. The Tisbury establishment was opened in 2019 by a Naples-born chef who cut his teeth working in kitchens in Italy and France, and today fills vacationers with comforting staples including rigatoni alla amatriciana, housemade lobster ravioli, and veal osso bucco in a white wine broth with saffron risotto.

An oversized porch sporting a row of white wooden rocking chairs is Chesca’s best advertisement, but the real action happens inside. After all, that’s where you’ll encounter chef Michael O’Brien’s Italian-inflected dishes, including bacon-wrapped, feta-stuffed dates, chopped littleneck clams with angel hair pasta and slow-cooked lamb bourguignon.

NANTUCKET

Yes, the Miacoment restaurant is located on Nantucket’s only 18-hole golf course. However, no tee time is required to partake in the veal schnitzel with brown butter spaetzle, pork tenderloin dips, or even a “Rodeo” burger topped by cheddar, bacon, chipotle ranch, barbecue sauce, and a couple of onion rings for good measure.

Now entering its 10th season on the Grey Lady, the Proprietor’s Table continues to push local palates with a globally inspired range of sharing plates including semolina cavatelli with fermented carrot butter, smoked beets with bearnaise and chili crisp, or even a whole trout accompanied by herbed butter and melted leeks. The cocktail menu similarly delights with inspired drams like the Strawberry Fields (pisco, guava, strawberry-infused vermouth) or the Chai Chai Slide (rye, masala chai, coconut cream).

Dune’s side-street patio is one of the more charming alfresco dining experiences the island has to offer, but the inside dining room marked by a quartzite bar is nothing to sneeze at either. Similarly, the long-running restaurant’s housemade mozzarella with roasted red pepper and cashew pesto or pan-roasted Atlantic halibut in a coconut lemongrass broth are always worthy of consideration.

Brotherhood of Thieves, which has wet local whistles since its 1972 founding, received a facelift of sorts in 2021 and now exits as four distinct concepts. Its mid-19th-century downstairs dining room continues on as Brotherhood of Thieves with blackened swordfish sandwiches and local drafts, while the upstairs has been transformed into Notch Whiskey Bar. Meanwhile, Cisco Kitchen & Bar will also dispense sushi rolls and nachos indoors while a beer garden on the outdoor patio offers suds and curly fries aplenty.

Entering its 50th year of service, cozy Company of the Cauldron — helmed by French Laundry vet (and Thomas Keller relation) Joseph Keller — marks special occasions with a French-influenced menu of American classics. On a given visit, that may mean the restaurant’s famous popovers followed by a bavette steak with caramelized shallots and a lobster-filled baked potato with a chocolate tart Chantilly to finish.

Spread across the eccentrically decorated dining room, bar and porch of the Greydon House hotel, Via Mare purports to be a Venetian-style bacari, but only “loosely” so, per the restaurant’s’ own admission. This means that you’ll encounter authentic cicchetti such as whipped salt cold with crispy polenta or trenette pasta with crab, but also hot chicken Milanese with Moroccan pancakes or spicy cumin lab with Sichuan peppercorns.