WHERE TO EAT
Check for seats at the upstairs bar of 21 Federal (21 Federal Street · 508-228-2121 · Dinner for two $100). The menu changes weekly and manages to be creative without adding that telltale sixth fruity ingredient that announces "Innovative chef at work." At the Boarding House (12 Federal Street · 508-228-9622 · Dinner for two $100), where reservations are required, Atlantic seafood gets the Pacific Rim treatment. On summer nights, the outdoor tables are hard to come by and hard to beat—there's a cheap bistro menu. The dining room of Topper's (508-228-8768 · Dinner for two $150), at the Wauwinet Hotel, is elegant in a restrained, gentlemen-will-be-more-comfortable-in-blue-blazers way. By all means, don't drive: take the complimentary boat ride to and from town.
SOMETHING OLD, SOMETHING NEW
Nantucketers love the Club Car (1 Main Street · 508-228-1101 · Dinner for two $125), a slightly stodgy standard. Don't be put off by the claustrophobic entrance through the last remnant of the old Nantucket railroad; once inside you'll find they do good things to sweetbreads. The couple who owns the Boarding House recently opened Pearl (12 Federal Street · 508-228-9701 · Dinner for two $150), which has a tropical-aquarium theme and requires reservations. The tuna martini is the best appetizer on the island.
LET'S GET ROMANTIC
A few blocks from the busy center of town but still in the historic heart, American Seasons (80 Centre Street · 508-228-7111 · Dinner for two $90) exudes warmth, particularly in the chilly shoulder seasons. Find out whether or not you and your date are compatible at the Company of the Cauldron (5 India Street · 508-228-4016 · Dinner for two $100): the lights are low, the tables snug, the mood intimate—and, since there's only one entrée each evening, you both eat the same thing.
OUT - OF - TOWNER
For French in the classic style, there's the Chanticleer (9 New Street · Siasconset · 508-257-6231 · Dinner for two $150). The main dining room feels more like a country-club banquet hall in suburban Maryland, but regulars know to ask for seats in the handsome bar, where the presence of smokers makes it all the more French.
TOP OF THE MORNING
Whether you sit at the counter or at one of the slightly cramped tables, the ambiance of Black-Eyed Susan's (10 India Street · 508-325-0308 · Breakfast for two $20) is casual. Breakfast is the specialty, though the coffee is a tad pedestrian. If you must have a jolt, get it at Espresso Café (40 Main Street · 508-325-0308).
SIDE BY SIDE
There are two classic old drugstore soda fountains in town, located in two classic old drugstores right next door to each other: Nantucket Pharmacy and David's Soda Fountain at Congdon's Pharmacy. For generations, Nantucketers haven't been able to make up their minds about which is better, so you don't have to either. But if you want a smoked Baltic sprat sandwich on rye, go to David's (47 Main Street · 508-228-4549 · lunch for two $10).