A mainstay of the Nantucket dining scene since 1985, this handsome, romantic cluster of rooms in a restored 1847 house is one of the toughest reservations in season (though Tommy Hilfiger doesn't seem to have a problem getting a table). But judging from a dinner visit, the people-watching might be a bigger draw than the food. Stick to the reliable and ever-popular surf-and-turf—a grilled half lobster with braised short ribs. The bar at 21 (as the regulars abbreviate it) is a popular gathering place after the kitchen closes, and the outdoor back bar is a little-known island highlight.

Dinner only. Open mid-May through mid-October.

With its harvest-scene murals and tables painted in quilt-style patterns, this "regional and seasonal" restaurant evokes old-fashioned Americana. (Sometimes to a fault—the rustic sign outside is so faded that you might miss the place.) Chef Michael LaScola organizes the new American menu into three culinary regions. For "Pacific Coast" he might spice-rub a Long Island duck breast and stuff dumplings with Nantucket-grown shitake mushrooms and foie gras. In a signature "New England" dish, he interprets fish and chips as potato-wrapped rare yellowfin tuna with crushed English peas and lemon confit. And for "Down South and Wild West," he might whip up a smoked tomato and bacon dressing for chicken-fried chicken livers.

Dinner only. Open mid-May through December.

Even fancy folks like John and Teresa Heinz Kerry have been known to wait on line for one of the 32 seats at this funky, diner-like café. The lines are especially long for Sunday brunch—the best on the island. Chef Jeff Worster (formerly of Citrus and Tulipe in Los Angeles) works his magic in the tiny open kitchen, changing the dinner menu every three weeks. His dishes span the globe: You might find tandoori chicken, southwestern red-pepper and chile soup, and a couple of Thai choices. Breakfast (served until 1 pm) is exceptional—especially the sourdough French toast with pecans and orange-Jack Daniel's butter. Credit cards are not accepted, and it's BYOB.

Open early April through October.

Compared to sister restaurant the Pearl, the Boarding House is more traditional in both decor and cuisine and has a more casual tone (encouraged by the lively bar). Unfortunately, the wait for a table is only slightly shorter. There's outdoor seating, but given the line of hungry diners wrapping awkwardly around it, request a table inside. The kitchen turns out simple, organic, largely local ingredients (principally fish and shellfish) prepared with Asian and Mediterranean influences, such as grilled swordfish with creamy eggplant; walnut-crusted salmon in a roasted tahini sauce; and seared sea scallops with asparagus, sunchoke, and jasmine rice cakes. For dessert, do as the locals do and order the cinnamon-sugar doughnuts with melted chocolate. The night doesn't end after the kitchen closes—this is where the staff members of other restaurants congregate after work.

Open May through September.

Reopened in 2001 after a fire, this friendly 1840s whaling bar in the basement of a Federal-style house is great for lunch and notable for its native quahog clam chowder, charbroiled burgers, and famous curly fries, which are thin, not too greasy, and perfectly salted. Lubricated by pints of local Whale's Tale Pale Ale and Dark and Stormy cocktails, residents and visitors mix easily here (a rarity in Nantucket town during the summer). Waits for a table are long at lunchtime, but a seat at the bar is more fun, anyway.

When the Chanticleer closed its doors in 2004 after three decades of serving the hautest French cuisine on the island, old-guard Nantucketers wrung their hands in despair. How could any restaurant ever replace the Chanti, an ivy-covered Sconset landmark that turned out perfect poisson grille and canard rôti? Luckily for them—and everyone else—Susan Handy and Jeff Worster, who reopened the Chanticleer in 2006, know exactly what they're doing. Worster and Handy (of Black Eyed Susan's, one of the hottest tables downtown) have preserved the classic French bent of the menu, but given it a less fussy, more modern spin. Alongside moules frites and steak au poivre are more adventurous dishes such as wild king salmon with coq au vin ravioli, and light-as-air cod beignets made with beer batter and served with red pepper aioli. The vibe has mellowed, too; while old-schoolers will still feel comfortable in their seersucker suits, jackets (and snooty attitudes) are no longer required.

Open June through October, closed Mondays in spring and fall; call ahead.

The candlelit tables fill up quickly at this tiny, refined restaurant where a harpist serenades the dinner crowd three nights a week. The prix-fixe dinner menu changes daily (it's posted on the Web site a week in advance), but loyal followers know that whatever chef All Kovalencik makes is bound to be good. Recent dishes have included pan-seared halibut over avocado salad with a coriander vinaigrette and Maine lobster-and-leek stuffed crepe with smoked shiitake emulsion. The portions are large and the prices (comparatively) reasonable, starting at $50 per person. There are either one or two seatings per night.

Dinner only. Open mid-April through mid-October.

On an island that abhors flash, the Pearl draws the cream of the see-and-be-seen celebrity crop and the hard-to-get reservations are prized (if you can't snag one, you can still eat at the bar). The dining room is also a stark departure from Nantucket typical—instead of dark wood and antique sideboards, one wall of the urbane, baby-blue space is an aquarium filled with darting tropical fish. The under-the-sea aesthetic complements chef-owner Seth Raynor's Asian-influenced seafood dishes, such as a "martini" of yellowfin tuna, wasabi, and crème fraîche; and tataki of day-boat sea scallops in a Chinese black bean vinaigrette. The spice-crusted, wok-fried local lobster with grilled lime and Asian barbecue sauce is the subject of constant debate—over whether it's Nantucket's finest lobster dish. Korean-style braised short ribs and tenderloin with foie gras–truffle jus will sate carnivores, but it's the fish that really sizzles here. There's also an impressive sake list, and a late-night menu served Thursdays, Fridays, and Saturdays until midnight that includes sashimi and satay.

Dinner only Wednesdays through Sundays, early April through late October; call ahead.

"Please, please tell me I can get one of your lobster rolls," we overheard a patron begging the woman behind the counter of the Rotary. We were a bit taken aback. Not only was he apparently desperate to shell out nearly $20 for a sandwich, but he was willing to do so at 8 am. But then our order arrived, and we understood—a split hero roll overstuffed with about three pounds of chunky claw meat, lightly dressed with mayo and crunchy bits of celery. We took it to one of the Formica tables and tucked in—with a knife and fork. This modest joint on the Nantucket Town rotary—a sort of navigational center of the island—also serves burgers, eggs, and other sandwiches, but it's the lobster rolls that have a following of ravenous addicts. Which is why they start serving them at 6 am.

Open Mondays through Saturdays.

Charmingly mismatched plates and cutlery, wine served in juice glasses, and French tables with antique schoolhouse chairs set the scene for Sfoglia's rustic, home-style Italian fare. Chef-owners Ron and Colleen Suhanosky—whose combined experience includes cooking stints at Florence's celebrated Cibrèo, New York's Gramercy Tavern, and Boston's Biba (where they met)—change up the menu twice a month but might dress fluffy gnocchi with a garden pepper-tomato sauce, bake Sicilian orata (sea bream) under egg white soufflé, or crisp chicken under a brick. Ultra-silky panna cotta and killer gelato are the work of Colleen, who cut her sweet tooth working under Gramercy Tavern's Claudia Fleming. In a reversal of the usual sequence of events, they opened a Manhattan outpost by the same name in early 2006 (1402 Lexington Ave.; 212-831-1402).

Open Mondays through Saturdays, December through September.

At this, the best place for dinner in Nantucket Town, Gabriel Frasca and Amanda Lydon (hot young chefs from Boston) specialize in unfussy preparations of local, seasonal produce and seafood. A single bright-pink prawn floated on top of sweet pea soup and a dollop of curried panna cotta is almost too pretty to eat (but too delicious not to); panko-crusted halibut fillet, fingerling potatoes, and tender baby artichokes strike a perfect balance of salty and sweet; and the crowd-pleasing Clambake combines buttered lobster with sweet corn, chorizo, and littleneck clams. The wainscoted dining room with a huge print of a striped bass is pleasantly summery, but when the weather's nice, reserve a table on the back porch, crack open a bottle of Spanish verdejo, and linger over dessert while the sun sets over the harbor. Lunch is served in the bar and on the front patio on weekdays, and brunch is offered on weekends, featuring ricotta pancakes with Nantucket blueberries.

Open mid-May through September.

Even if you're not staying at the Wauwinet, hop aboard the hotel's free shuttle boat, the Wauwinet Lady, at Straight Wharf for the short, scenic cruise to lunch or dinner. Chef David Daniels (Acqua in San Francisco, Ventana Inn in Big Sur, XV Beacon in Boston) puts a gourmet spin on standard dishes: His steak is a Kobe sirloin au poivre with cognac sauce, and he gussies up mac and cheese with cave-aged Gruyère, Gouda, Pouligny chèvre, and truffles. The island-famous hamburger—served only at lunch—is part Kobe beef, part short rib, and topped with Dijon mustard, capers, and caramelized onions. French pastry chef Serge Torres finishes the meal with candied cherry tomatoes and vanilla ice cream or bananas Napoleon. The Wauwinet also has the most extensive wine list on the island. In summer, lunch ($21 for the prix fixe menu) is served on a deck overlooking the water; at dinnertime, and in cooler weather, a crackling fire warms the elegant dining room.

Open early May through late October.

Lunchtime crowds in Nantucket Town stressing you out? Avoid them altogether at this hole-in-the-wall takeout bakery. The sandwich selection (all on fresh-baked organic bread) includes spiced grilled lamb, cucumber, and yogurt sauce on a warm baguette and fresh mozzarella, roasted red peppers, and eggplant between hunks of olive bread. A bag of chips, a natural soda, and a handful of napkins are all you need for an impromptu picnic; park benches at the Easy Street Boat Basin are just a block away.

Open early April through December.