Nantucket's Sea-Washed Charm

Happy Hour Spot: Cru – Rosé and local oysters on the dock, waterfront people-watching
Population: 11,800
Coffee: Handlebar Cafe
Best day of the year: Daffodil Festival, April

Thirty miles off the coast of Cape Cod, Nantucket is about 15 miles long and 3 miles wide—an “elbow of sand,” wrote Herman Melville. Once the Whaling Capital of the World, the tiny island is now a tony summer retreat, known for gray shingled houses, sailboats, clambakes and 50 miles of (mostly) quiet beaches. A bike is the best way to get around: Rent one from Young’s on the Steamboat Wharf and ride to Something Natural, just outside town, for sandwiches on homemade herb bread and a freshly baked cookie for the road. The 6-mile Madaket Road Path offers glimpses inland: ponds, hills and the Madaket Mall—the “take it or leave it” where locals trade treasures at the town dump. Before you ride to the beach, stop at Millie’s for a Madaket Mystery, a rum punch made here for decades.