For an island of only 52.5 square miles—one-twentieth the size of Rhode Island—Nantucket punches above its size when it comes to dining, a reflection of the demand for quality food during the summer season.
From April through December, Tradewind offers as many as 25 flights per day to Nantucket, starting at 6:00 a.m. through 7:00 p.m., from the private terminals at two New York area airports.
Here's the Tradewind aerial survey of the island's culinary offerings, organized by the sort of place you're craving upon landing.
Haute Nantucket: Topper's
This waterside restaurant, an arm of The Wauwinet—the island's most luxurious hotel—is a luxe enclave of New American cuisine. There's lobster, but it may come butter-basted and with carrot-truffle dumplings and a vanilla Lillet Nage—you get the idea, New England gone to culinary school. Even the Mac'n'Cheese is not exempt: it’s actually truffled Rigatoni with melted Gruyère, Gouda, and Pouligny Chèvre.
Echoes of Asia: The Pearl
Located in Nantucket town, this Asian-inflected—but locally sourced—menu is inspired by the travels of chef Seth Raynor. One example: Green Thai coconut curry with tofu and pineapple.
Breakfast Writ Large: The DownyFlake
The specialty: flaky housemade doughnuts, but don't overlook the crisp-edged pancakes. Otherwise, whatever breakfast you want, all day long. An institution—80 years old in a gray-shingled diner.
Tradition by Day, Hip by Night: The Galley
A Nantucket family-owned stalwart that originally started as a clam shack back in 1958. At lunch the rattan-furnished dining room, which looks out on the Cliffside Beach Club, draws Nantucket's old guard (it's been an anniversary spot for decades), but by night there's a trendier scene in the back room.
Globe Spanner: LoLa 41°
A very chic waterside place just a block west from Children's Beach. The concept: a menu inspired by cuisine along the 41st parallel, which is not a bad line to toe as it takes in sushi, sake, Spanish and Greek cuisine, among others.
La Vida Loca Locavore: American Seasons
The menu's brilliance comes from chef Neil Ferguson's partnership with island farms and passion for the waters. The two come together beautifully in day-boat scallops with fried green tomatoes and lemon confit.
You're in the Hands of the Chef: Company of the Cauldron
Allen Kovalencik offers a fixed menu each evening (Monday's is all about lobster), so if you're the type who hates deciding, this is the spot, given the chef's deft hand with a spectrum of dishes (rosemary-skewered shrimp to Beef Wellington with a wild- mushroom duxelle). Lose control.
Dockside Reinvented: Straight Wharf
General Manager Christopher Sleeper and Executive Chef Mayumi Hattori gave this Nantucket institution a menu-lift without losing the atmosphere: hurricane lamps, butcher-paper tablecloths, and dish towels as napkins. The catch is local (do "harpooned local swordfish" meet your locavore standard?) and so are the crops. There's also traditional fun, the "swr clam bake".
Pizza: Pi Pizzeria
Nantucket's only wood-fired pizzeria owned by Evan and Maria Marley. Pies are wider and flatter than the classic Neapolitan, but otherwise in that style: super-thin middles, raised edge crust, San Marzano tomato sauce, small pools of mozzarella and prosciutto San Daniele on top.
Wine and Cheese on Landing: Table No. 1
Owner Sarah Powers brings beaucoup international experience—Krug Champagne, Cakebread Cellars, Johnny Walker Blue, and Wines of Chile—to this new venture on the wharf. "Small batch, high-quality, and hand-crafted" is her mantra. The place to provender a picnic or stock the house for the first night.