Just a few blocks beyond Nantucket’s downtown fringe, American Seasons has the air of a longtime classic but the cuisine of a hip new spot. Foodies delight in the farm-to-table dishes, which may include such tastes as carrot soup with cream cheese falafel and bulgar wheat risotto with farm egg and fried pickled ramps in a baked potato broth. With a wine list with over 500 titles, American Seasons is the perfect spot for a romantic evening, especially when dining in the garden patio.

There’s still no easy way of getting into this island favorite—reservations are accepted only for dinner—but locals and longtime visitors have accepted the fact that lining up in front of the unassuming restaurant is part of the experience. Opened in 1992 by chef Jeff Worster and Susan Handy, the BYOB restaurant has a small dining room with white-washed walls and green copper chandeliers, as well as a lovely outdoor dining space. The hearty breakfast, served until 1 p.m., is the most popular; arrive early and be prepared to wait.

Opened in 1958, Galley Beach is an island classic due to its spectacular location on Cliffside Beach. The beachside dining room offers unrivaled sunset views, and after a 2008 renovation the iconic eatery is sophisticated without being too sleek. While the food is not outstanding, the view is breathtaking, and Galley Beach remains the see-and-be-seen spot for summer locals.

Few customers actually order juice at this simple shop at the corner of Broad Street; instead they line up for delicious homemade ice cream and sorbets (if you’re lucky, you’ll arrive in time for their famous blackberry, made with locally harvested fruits). For the ultimate indulgence, get an ice-cream sandwich made to order with your choice of flavor between two homemade chocolate-chip cookies. The housemade waffle cones are another favorite.

An island institution, this French go-to is always packed with locals and summer visitors, usually found catching up on island gossip with the friendly staff. There’s a formal dining room upstairs, but follow the locals’ lead and get a seat at the bistro downstairs. There are just seven tables, covered in blue-and-white-checked tablecloths, and the menu includes such haute-brasserie favorites as sweetbreads, filet of sole, rib eye and lobster. Those waiting for a table can have a glass of wine at the zinc-clad bar.

A no-frills clam shack overlooking the harbor, the popular Lobster Trap serves up fresh seafood. The spot also has a special children’s menu.

If you’re biking toward Nantucket town along the challenging—and aptly named—Cliff Road and suddenly get a whiff of freshly-baked bread, you know you’ve arrived at Something Natural, a lunch standby located in a cottage surrounded by a large garden. The sandwiches are prepared on tasty homemade bread (they also sell muffins and pastries). It’s a good spot to stock up before a bike tour, or take a break at one of the picnic tables scattered across the lawn. For those who can’t get enough of their lauded chocolate chip cookies, quarts of dough are available for sale.

Despite opening 1975, Straight Wharf has never gone out of style or aged one bit; in fact, it’s as popular as ever, enticing patrons with watermelon and tomato salad, arugula and French green olives and zucchini-blossom appetizers. For a drink at sunset, the simple wooden bar inside the main dining room and the patio overlooking Straight Wharf are always crowded. This is not the place for an intimate cocktail (for that, go to Òran Mór), but to see and be seen, there’s no better location on the island.

This Nantucket institution stocks everything from bug repellant to suntan lotion, but the soda shop up front is the real treasure. The old-school-style diner serves a simple breakfast as well as thick milkshakes and soda floats.

The restaurant of the Wauwinet, Topper's, remains at the top of the Nantucket dining scene. The innovative menu is mostly a riff on French cuisine, with the occasional Asian, American or Italian touch. Memorable past dishes include a creamy lobster bisque, branzino with summer vegetables and perfectly prepared Wagyu beef sirloin. The more formal white dining room has banquet seating, large tables and is furnished with antiques, but the gracious service ensures that it never gets stuffy. More casual is the patio, where guests are seated on cushioned wicker chairs, with sea views in the distance. While children are normally not allowed, they can join for the first dinner seating of the evening on the patio.