Built in 1709, the nine-room Woodbox Inn (29 Fair St.; 508/228-0587; doubles from $155) makes Nantucket's 19th-century houses look dreadfully nouveau. Nobody has wider floorboards or smaller windowpanes—and nobody, but nobody, has better popovers. An old silk factory is now the Sherburne Inn (10 Gay St.; 888/577-4425 or 508/228-4425; doubles from $150), with eight larger-than-average rooms. Some of the 12 rooms at the Nesbitt Inn (21 Broad St.; 508/228-0156; doubles from $65) are frayed—in a Victorian way—but the location near the ferry terminal couldn't be better. Among the best of Nantucket's many guesthouses are a pair owned by the Carl family. Mom and Pop oversee the five-room Chestnut House (3 Chestnut St.; 508/228-0049; doubles from $150). Next door, their children run the 10-room Hawthorn House (2 Chestnut St.; 508/228-1468; doubles from $145).
After a few seasons at Wade Cottages (35 Shell St., Siasconset; 508/257-6308; doubles from $240, three-night minimum), you'll feel as if you're returning to your family compound. The effect might be due to the stairway down to the beach; the well-used beach chairs; the relaxed owners; or the charming accommodations in eight rooms, six apartments, and three cottages.
The Wauwinet (120 Wauwinet Rd., Wauwinet; 800/426-8718 or 508/228-0145; doubles from $380) is unmatched. One of the first resorts built on the island, it now has twice as many staff members as guests—not to mention bikes, kayaks, croquet and tennis courts, and sailboats. The service is impeccable, though some of the 35 rooms are so cozy that you feel you'd better pass up room service for lack of space to put the tray. On a bluff in Sconset there's the most romantic getaway: Summer House Cottages (Ocean Ave., Siasconset; 508/257-4577; doubles from $550). The 10 rooms are really self-contained little rose-covered cottages, all arranged around a garden.
Don't have a reservation?Check for seats at the upstairs bar of 21 Federal (21 Federal St.; 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 St.; 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.
Nantucketers love the Club Car (1 Main St.; 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 St.; 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.
A few blocks from the busy center of town but still in the historic heart, American Seasons (80 Centre St.; 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 St.; 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.
For French in the classic style, there's the Chanticleer (9 New St., 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.
Whether you sit at the counter or at one of the slightly cramped tables, the ambiance of Black-Eyed Susan's (10 India St.; 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 St.; 508/325-0308).
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 St.; 508/228-4549; lunch for two $10).
With a few exceptions, the best shops lie in the historic heart of town, along Main, Federal, and Centre Streets.
Originally produced during long hours at sea on floating lighthouses, the Nantucket lightship basket is now an institution. The intricately woven lidded baskets can be found at practically every shop along Main Street, but the finest are sold by a few venerable craftspeople. The best sources are the Ottisons (170 Orange St.; 508/228-9345) and Nap Plank, who runs Nantucket Basket Works (14 Daves St.; 508/228-2518).
Since 1913 Murray's Toggery Shop (62 Main St.; 508/228-0437) has been home to the famous "Nantucket red" trousers, the Sperry Top-Sider, and everything else the locals have been wearing from the time they were in boarding school. Peter Beaton Hat Studio (16 1/2 Federal St.; 508/228-8684) is the source for those lovely straw hats with the upturned brim and wide ribbon you see all the women wearing. If the fog has rolled in and raised goose bumps, Cashmere Nantucket (32 Centre St.; 508/228-7611) is your savior.