Nantucket

Nantucket Island is 48 kilometres south of Cape Cod. IR TRANSPORTATION Photo provided by Nantucket Island Resorts.

In the summer months, Nantucket resembles a well-bred beauty playing host to the good life: gorgeous families—collars popped, ice cream cones in hand—wandering through cobblestone streets; the tang of salt water and Polo Sport commingling with the unmistakable aura of old money. Once autumn arrives, however, the host slips off her sunglasses and assumes a quieter pace.

Exploring Nantucket in September, near the end of the tourism season, offers a fascinating glimpse into the allure of this tiny island located 48 kilometres south of Cape Cod, Massachusetts. As the seasonal population shrinks from about 50,000 to 10,000, the action moves away from the wharfs and beaches to the town’s galleries and charming cafés, now serving warm apple cider instead of icy lemonade.

The fall crispness also sends visitors into the white-pillared splendour of the Nantucket Atheneum library, which houses first-edition tomes by Herman Melville, who based his 1851 classic Moby-Dick on a Nantucket whaling disaster without ever having stepped foot on the island. (He did eventually visit, six months after the novel was published.) Such is the power of Nantucket’s mythology, which also sparked the imagination of John Steinbeck, who wrote East of Eden here, and an 11-year-old Ernest Hemingway, who penned his first short story, titled “My First Sea Vouge” [sic], after visiting the island with his mother.

The ocean and its mysterious depths are embedded in Nantucket’s appeal. Founded in the mid-1600s by English settlers, the island—just 22 kilometres long and six kilometres wide, “an elbow of sand”, as Melville quipped—quickly became the world’s whaling capital. When the industry collapsed in the 1840s, Nantucket emptied out like an abandoned château in a fairytale, but by the 1880s, with the tradition of the summer vacation firmly established, it once again became a tourism mecca. This ebb and flow of the American dream ensured the longevity of Nantucket’s pre–Civil War architecture—most notably, the houses with lovely weather-beaten grey shingles and cream trim that dot the island. Today, building codes are protectively strict: there are no traffic lights, billboards, neon signs, or franchises, except for a lone (initially maligned, now accepted) Ralph Lauren boutique.

The Wauwinet Inn.

The island’s signature luxury is elevated to new heights at the exquisite Wauwinet inn, located about 15 kilometres from the centre of town, past salt marshes and cranberry bogs, on a slip of land between the Atlantic Ocean and Nantucket Bay. Imbued with nautical chic, it’s the kind of place where you’d expect to see a pristinely groomed Labrador retriever ambling down the hallway wearing a designer kerchief. The cozy elegance of the 30 rooms and suites, and two cottages, is spiked with thoughtful touches: swish Pratesi linens, daily fresh blooms, and the joy of borrowing one of the inn’s 200-plus DVDs and having a staff member knock on your door bearing hot buttered popcorn.

Downstairs, the library is stocked with retro board games and an afternoon spread of port, sherry, and cheese. Take your aperitif outside and stroll by the lapping waves, or admire the cerulean shades of the sky and sea from a white wicker deck chair. At the on-site Topper’s restaurant, executive chef Kyle Zachary’s skill is on display from brunch to dinner. Indulge in the butter-poached lobster or heritage-breed suckling pig paired with Black Mission figs and violet mustard, and linger over the Wine Spectator–approved wine list, 1,450 labels strong.

Back in town, the White Elephant hotel (the Wauwinet’s sister property) boasts ultra-luxe vacation rentals called the Residences—apartments that give any of the Nancy Meyer set a run for their money. The linens are organic cotton, the china is Royal Doulton, and amenities include such necessities as a panini press. This past summer also saw the opening of a new Inn, which, combined with the Residences, forms the White Elephant Village; centrally located, it’s an ideal jumping-off point to explore the harbour and downtown core. Rent a bike and discover 48 kilometres of cycling trails, or browse Murray’s Toggery Shop, which introduced the famous Nantucket Reds—salmon-hued pants—to the world.

Or take a meditative stroll into a residential neighbourhood, past white-steepled churches, rippling flags, and leaves deepening into olive ochre. Nantucket’s singular charm resides here, among the people who love it year-round, combining the best of American ideals—independence and glory.

Air transportation provided by Porter Airlines and Cape Air. Photos provided by Nantucket Island Resorts.