The cobblestoned streets of Nantucket Town (Nantucket is the name of the island, the county, and the main town) look like the prototype for Ye Olde Villages everywhere. In the eastern town of Sconset, the post office serves as a central meeting spot, as it has for the past 106 years. And all across the island, the biggest badge of local pride is a worn-out Jeep, with years’ worth of beach permits—the more, the better.
Given Nantucket’s respect for tradition, it’s hardly a surprise that even the latest developments are focused on preservation. Wendy Schmidt, wife of Google CEO Eric Schmidt, recently swooped in to save Mitchell’s Book Corner (54 Main St., Nantucket Town; 508/228-1080), a 40-year-old store on Main Street that was in danger of closing. And Nantucket social fixture Linda Loring turned over 270 acres of her property—the largest remaining privately owned, unprotected tract—to the Nantucket Land Council; they’re now part of more than 13,000 acres (40 percent of the island) designated as conserved land, most of which is open to the public.
But even the classics welcome an update. “There’s been an infusion of new ownership and energy,” observes Amanda Lydon, co-chef of the recently reopened Straight Wharf Restaurant (6 Harbor Square; Nantucket Town; 508/228-4499; dinner for two $75), Nantucket’s answer to Chez Panisse. She and her partner, chef Gabriel Frasca, prepare playful takes on summer staples, such as a “deconstructed clam bake.” And island stalwart The Wauwinet (120 Wauwinet Rd.; 800/426-8718; wauwinet.com; doubles from $380)—famous for its breakfasts of lemon-ricotta pancakes or eggs with smoked salmon and caviar—has added the airy Spa by the Sea. The treatment rooms announce their names—Sea, Sun, Sand, and Sky—with shell-covered plaques on the doors, and mid- massage, you can see (and hear) the Atlantic lapping at the nearby shore.
Staying in one of Susanne and Wade Greene’s six cottages (two-week minimum) or five apartments (one-week minimum) is like crashing the family compound. Rooms are austere affairs (lace duvets, unrenovated bathrooms), but outside, beach chairs, Boogie boards, and all manner of floating toys are yours to borrow. 35 Shell St., Sconset; 508/257-6308; wadecottages.com; apartments from $1,900 a week.
Set right on Nantucket Harbor, this hotel has the amenities and services of a large resort, along with easy access to countless restaurants and shops. The 64 rooms are decorated in a simple, beachy style, with cream-hued bedspreads and pine and cherrywood furniture. 50 Easton St.; 800/445-6574; whiteelephanthotel.com; doubles from $600.
Labels like Bono’s Edun and Nicole Miller Collection fill the racks at this new eco-chic clothing shop in downtown Nantucket. You’ll also find vintage Missoni dresses and a collection of wicker purses. Zero Washington St., courtyard; 508/228-7818.
Nantucket Stock Exchange
A hand-carved wooden sign bearing golden whales and a big American flag mark the outside of this off-the-radar gray- shingled cottage that teems with antiques: vintage postcards of the Nantucket Yacht Club, whale-shaped ashtrays, weathered wooden buoys, and Nantucket Railroad signs. 25A Old South Rd.; 508/228-9155; nantucketstockexchange.com.
It’s worth the inevitable wait for one of the 32 seats below the antique chandeliers at this local brunch favorite. Be sure to try the veggie scramble with sides of black-eyed peas and grits. 10 India St.; 508/325-0308; brunch for two $20.
From 1881 to 1917, a railroad ran from Nantucket Town east to Sconset. A narrow vintage train car from that period now doubles as this kitschy piano bar, the go-to spot for gossiping over dark ‘n’ stormy cocktails. 1 Main St.; 508/228-1101; drinks for two $20.
Pick up fixings for a beach picnic at this unassuming joint, where East Coast luminaries (think John Kerry in swim trunks) come for oversize sprout, veggie, and avocado sandwiches. 50 Cliff Rd.; 508/228-0504; lunch for two $20.
T+L Tip sheet
When to Visit
The island is at its peak in the summer. Locals generalize that July is for Bostonians, and August is for New Yorkers. The rest of the year—in particular May, June, September, and October—is for people willing to sacrifice a few hours of sun for empty swaths of sand and easy reservations.
Best Bike Rental
If you’re staying in town, there’s no need to rent a car. Nantucket’s bus system is highly efficient, and bicycles are the best way to beach-hop during the day (26 miles of bike paths trace the shore). Young’s Bicycle Shop (6 Broad St.; 508/228-1151; youngsbicycleshop.com; rentals from $25 a day) is the time-honored spot for renting cruisers and Bianchis; it offers discounts if you book online.
Best Island Map
Pick up the free weekly newspaper Yesterday’s Island (yesterdaysisland.com)—found in most local shops and restaurants—for a detailed map of the island.
Gene Mahon, Nantucket’s unofficial mayor and 38-year full-time resident, offers photographs and inside information about the island’s best events and openings on his blog, Mahon About Town (mahonabouttown.com).
Nantucket has 82 miles of sandy coastline.