Boston: Cuttyhunk
Credit: Bill Greene / The Boston Globe / Getty Images

Before the Pilgrims climbed aboard the Speedwell, English settlers were already fishing the waters off Cuttyhunk Island just south of Cape Cod. The small island was attractive because of its protected mooring area, sandy beaches, and strategic position near the mainland at the north of Vineyard Sound. Today, the island is a summer destination for the in-the-know and the wealthy, who bike between old farms and the colonial village near where the ferry arrives on the island. Part of Gosnold, the town is home to roughly 50 people who buckle up against the harsh winter winds. Come summer, hundred spend their weekends here bathing in the sun and the calm surf and wearing the sort of swimwear that would have raised eyebrows back in the seventeenth century.

More information: Pedestrian ferries leave frequently from New Bedford. The Cuttyhunk Fishing Club is the best place to stay in town. Just be sure to book rooms in advance, the place is very popular with Boston Brahmins.