[8] In 1641, Thomas Mayhew the Elder, of Watertown, Massachusetts, bought the islands—along with Nantucket and Martha's Vineyard—from William Alexander, the Earl of Stirling.

[10] Before the creation of the Province of Massachusetts Bay in 1691, the islands were part of the extinct Dukes County, New York.

The first known European inhabitant was Francis Usselton, who had been banished at the time for making secret trades with the local Indians without consent from the governor.

[11] The total land area of the islands is 34.55 km² (13.34 sq mi); and there was a permanent population of 75 persons as of the 2010 census, making it the smallest town in Massachusetts.

Currents of up to 6 knots (11 km/h) are driven by the different sizes and filling rates of Vineyard Sound to the southeast and Buzzards Bay to the northwest.

Listed from northeast to southwest, the named channels are: There are many bluefish and striped bass found in the waters near all the islands.

Some of the most popular include Nashawena Island’s Highland Cattle, Tarpaulin Cove Lighthouse, Gay Head Cliffs, the Naval Lookout Point on Cuttyhunk, and a plethora of wildlife.