1. Where to Stay
Shoe designer turned hotelier Vanessa Noel caters to the trend-obsessed with her two boutique hotels in the heart of Nantucket. The Vanessa Noel Hotel goes heavy on the heavenly whites, the bathrooms sparkling with Philippe Starck fixtures and the funky, ground-floor Café V looks transported direct from Nolita. Though fashion-forward, the small quarters (there are just eight rooms, all wedged into a historic 1847 building) aren’t suited to families with small kids.
Next door, Noel’s newly opened Hotel Green offers the island’s only ecoconscious lodgings: The furniture comes from recycled materials; the cleaning products are all biodegradable; and the wall paint is milk- rather than latex-based. Bring kids and pets, but if either is bigger than a carry-on, you might want to reserve the one suite.
Traditional, country-club Nantucket lives on at the Wauwinet, set on the island’s northeastern coast far from Nantucket town (although a free jitney runs there several times daily). Rooms and cottages are outfitted in tasteful chintz, with Pratesi linens and fresh-cut flowers. The on-site Spa by the Sea gives caviar facials, and Topper’s restaurant pairs excellent Bloody Marys with outrageous sunsets.
2. Where to Eat
Flash back to your last Hamptons weekend at the slick, dinner-only LoLa 41 (15 South Beach St.; 508-325-4001). Chef David Edgar’s menu literally spans the globe with cuisines that touch down in every country on the 41st parallel—that means Japanese-inspired sashimi, a Greek soft-shell crab, and a half-dozen Northern Italian pastas. The best bet, though, might just be the American Black Angus sirloin burger, topped with caramelized onions and Wisconsin Cheddar.
Hit the sweet spot between old and new Nantucket at Straight Wharf Restaurant, which has been around for more than 30 years but was revived by two young Boston chefs in 2006. The menu changes with the seasons and September’s an especially good time to drop by. Fall entrées include the tender, braised rabbit with homemade carrot gnocchi, and a clambake with local corn fondue. The back deck looks right onto the harbor—ask for a table “along the rail.”
If you like your green vegetables truly green, check out Water Street, a cozy bistro where all of the meat, most of the produce, and a handful of the wines are organic.
Sing for your supper at the Summer House Restaurant in the East Coast village of Siasconset. Plenty of polo-shirted, sunburned-from-the-sailboat types (and, recently, Katie Couric) follow their filet mignon au poivre dinners with boozy Cole Porter impressions at the piano bar.
3. What to Do
Shopping in Nantucket Town has gotten almost unrecognizably chic over the past few years. A pair of stilettos isn’t the obvious choice for tackling the island’s cobblestone streets, but women who must have a new pair of Jimmy Choos (or a Brioni blouse or Ferragamo handbag) can swing by David Chase. Fancy undies—Cosabella camisoles, Natori chemises—are right around the corner at Ladybird Lingerie. And shelter-shop hounds who can’t live without another John Derian découpage plate or embroidered Ankasa throw pillow should visit Trillium.
Once you’re done shopping, absorb the season’s last rays at one of Nantucket’s justifiably famous beaches. Sheltered north-shore strands like Jetties and Children’s Beach are within walking distance of town. (Jetties is much bigger and has a casual sit-down restaurant with great clam chowder.) Surfers should head to wilder southern-coast beaches like Surfside, Miacomet, and Cisco, though there’s limited parking, so arrive early on big-swell days. To the far southwest are the windswept dunes and spectacular sunsets of Madaket; bring a blanket and a bottle for sundowners among local families.
4. Insider’s Tip
The East Coast village of Siasconset (called “Sconset”) is admired for its centuries-old cottages covered with climbing roses. Less known, though, is the intentionally unmarked Bluff Walk, a neighborhood walking trail that brings you right through the backyards of some of Sconset’s most opulent waterfront homes. The homeowners put up with the occasional strollers, so long as they’re respectful and stay on the walking trail. (By fall, many of the occupants have headed back to the mainland anyway.) The walk starts at the end of Front Street, at the ocean end of Sconset’s town square. Bypass the small sign that says “Footpath Only, No Bikes” and take the path to the left, cutting past some hedges and across the first lawn. Erosion over the past few years has made the last quarter-mile or so unsafe: When the track suddenly disappears among scrub and boulders, you’ll know to turn back.
5. Oddball Day
To commune with Nantucket’s wild side, head to Great Point, the sweeping peninsula at the island’s northeastern tip. There’s no road along this seven-mile stretch of dunes and beach—it’s protected preserve land—so the only way to get here is by driving a 4x4 right on the sand. Young’s Bicycle Shop on Straight Wharf in Nantucket Town rents open-top Jeep Wranglers. Pay a $25 entry fee and reduce your tire pressure, then four-wheel all the way to the Great Point Lighthouse at the end of the spit. Along the way, you’ll see some of the island’s most dramatic, and empty, stretches of beach. Bring lunch—the takeout counter at Water Street Bakery, right down the street from the jeep-rental shop, has terrific sandwiches—plus plenty of water and sunscreen, and spend the rest of the day with piping plovers, the occasional surfcaster, and harbor seals bobbing offshore.
6. Related Links
The alternative transportation group Wheels, Heels & Pedals provides information on Nantucket biking, hiking, and public transportation.
Click around Yesterday Is Today for weekly listings of gallery shows, wildflower and ecology walks, and free concerts.
Daily weather and surf conditions for all Nantucket’s beaches are posted on Nantucket.net.
Society scribe Gene Mahon chronicles the island’s old-guard soirées (with party photos à la Town & Country) on his Mahon About Town blog.