Island Airlines was a commuter airline headquartered at Barnstable Municipal Airport in Barnstable, Massachusetts, United States which operated hourly scheduled flights between the island of Nantucket and Hyannis, Massachusetts.

Milton "Red" Hersberger, a former Chicago barnstormer, developed the first aerial transport to the island in 1930, beginning with two biplanes, and acquiring his first Ford Trimotor in 1932.

His first Trimotor was purchased after it had crashed in the mountains near Pittsburgh; after it was repaired and put into operation, it was so useful that four other examples soon joined the fleet.

[2] After World War II, Hersberger was able to buy several hundred surplus engines from the US government for use in the Trimotors; they cost fifteen dollars each.

The airline has since added three more Grand Caravans and plans to eventually transition to an all-Caravan fleet.