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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.
For anything from a beachside cottage to a sprawling manse, look to Congdon & Coleman (508/325-5000; congdonandcoleman.com) or Island Properties (508/228-6999; islandpropertiesre.com).
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.
If Ralph Lauren had married Lilly Pulitzer, their sons would shop here. Ties in nautical patterns, woven belts, madras shorts, and lobster-print totes are equal parts preppy and cheeky. 18A Federal St.; 508/325-4449; eyeoftheneedleinc.com.
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.
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.
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.
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.
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