For the island charm
Talk to folks on Nantucket, and you’ll find a refreshing determination among visitors, seasonal residents and locals alike: We’re not taking this place for granted. More than pretty beaches and what’s-down-that-private-drive? homes, the island has an unexpectedly unstuffy vibe; an impressive amount of green space thanks to dogged conservation efforts (see your first cranberry bog!); a rich history of entrepreneurs (Macy’s, Folgers coffee) and whaling (Herman Melville owes many a Moby-Dick detail to the place); and deep Quaker roots that will appeal to Philadelphians. This is where Chris Matthews has a home and veep Joe Biden traditionally celebrates Thanksgiving, and while there’s a distinct red-white-and-blue energy with a summer crush of crowds on the cobblestone streets, those in the know will tell you that without a doubt, the more placid fall is the best time to go. —Janine White
BEDDING DOWN: The Wauwinet (120 Wauwinet Road, 508-228-0145; open through October; from $225 a night) is a romantically remote inn about 20 minutes’ drive from the island’s town center. Charm is a given, of course, but the warm service and complimentary amenities (afternoon port and cheese in the library, hot popcorn delivered to your room in a porcelain tureen with your DVD loan from the front desk) are flawlessly executed rather than merely tacked on. For families or groups, the townhouse-style accommodations at the White Elephant Hotel Residences (50 Easton Street, 508-228-2500; from $350 a night in the fall) are central to everything and offer kitchen, living and dining areas (and turndown service, too).
DINING: The finest dining on the island is at Topper’s at the Wauwinet. Beeline to the gastronomic-heaven part of your vacation by opting for exec chef (and Walnut Hill grad) Kyle Zachary’s seven-course tasting menu. Right by the town’s ferry landing is the Juice Bar (12 Broad Street, 508-228-5799), for smoothies and ice cream. The line’s long for good reason.
STATE FARE: Tender, rich Nantucket Bay scallops are in season through the fall. (Scalloping is still big business on the island.) Your best bet for sampling the local harvest is the Pearl (12 Federal Street, 508-228-9701), which has won seafood awards aplenty.
PASTIMES: Rent a bicycle (they’re complimentary if you’re staying at the White Elephant) and pedal out to middle-island Cisco Brewers, where you can hang out in the rustic tasting barn and sample local beers like Whale’s Tale Pale Ale and Captain Swain’s Extra Stout.
DAY TRIP: You can soak up the island’s history most keenly in the frozen-in-time village of Siasconset—just ’Sconset to locals—where twee wood-shingled cottages originally inhabited by seasonal whalers still stand.
GETTING THERE: If you don’t fear the mating of the words “tiny” and “plane,” fly directly onto the island by connecting through Boston or Providence. (Save yourself the Logan headaches and choose the latter.) Or you can fly to either city, rent a car, and drive to Hyannis to catch a ferry.