Island Airlines

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. He called the operation Erie Isle Airways. 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. 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.

Hersberger renamed the airline Sky Tours and sold it in 1953.. It was sold again in 1973. It received its current name in 1991 when ownership of the operation was assumed by William McGrath.

As of June 2013, Island Air's fleet consisted of the following aircraft:

Cessna Grand Caravans

In January 2009, Island Airlines announced the addition of a Grand Caravan to their fleet, becoming the first airline in over 30 years to add a new type of aircraft to the Hyannis/Nantucket route. The airline has since added three more Grand Caravans and plans to eventually transition to an all-Caravan fleet. Island Airlines was the only airline flying this type of aircraft between Hyannis and Nantucket, a market traditionally dominated by the twin–engine Cessna 402.