You won’t hear it mentioned alongside Nantucket’s  yacht-filled wharfs or Martha’s Vineyard’s  sophisticated restaurants anytime soon, but that may be precisely what makes Cuttyhunk Island so inviting.
With just a small handful of businesses and restaurants (including a pizza joint, a casual hotel serving weekend brunch, a gift shop, and a post office), little-known Cuttyhunk is where to come when you don’t just want to get away from it all, you want to get away from it all. That includes cars, too; golf carts and bikes are the preferred method of transport all over the island.
A word of warning: Hit the ATM before boarding the ferry, as there aren’t any on-island, and credit cards are rarely accepted.
But what Cuttyhunk Island lacks in luxury it makes up for in history and heartstopping natural beauty. Situated in the far southwestern corner of the Elizabeth Islands, the two-mile-long Cuttyhunk was actually one of the first pieces of America spotted by British explorer Bartholomew Gosnold (all of the Elizabeth Islands together comprise the town of Gosnold). And not terribly much about the island has changed since then, thanks to enormous conservation efforts that have kept the epic marshes clean, the woods intact, and the water views unsullied by McMansions or huge hotels.