Nantucket is a boomerang-shaped island 26 miles southeast of Hyannis on Cape Cod, or 107 miles southeast of Boston. Its nearest neighbor to the west is the somewhat larger island of Martha's Vineyard; eastward, the nearest landfall would be the Azores off Portugal. The island has only one town, which also goes by the name of Nantucket. The only other community of note is tiny Siasconset, a cluster of shingled seaside manses and lovingly restored fishing shacks 8 mi west of town. A 3-mi main road directly south of town leads to Surfside Beach, among the island's most popular. Nantucket's small but busy airport is located east of Surfside.

Nantucket Town. As the ferry terminal—from Hyannis and, seasonally, Martha's Vineyard—Nantucket Town is the hub of all activity and the starting point for most visits. At the height of summer, the narrow cobblestone streets are in a constant state of near-gridlock. Town itself is easily walkable, and bikes are available for exploring.

Siasconset and Wauwinet. An allee of green lawns leads to the exclusive summer community of Siasconset (or 'Sconset, as locals say). Tucked away on either side of the village center are warrens of tiny, rose-covered cottages, some of them centuries old. About 5 mi northwest is the even tinier community of Wauwinet, with the country's second-oldest yacht club.