It All Started With Seaplanes, Smuggling and Booze

The airline was founded by Arthur "Pappy" Chalk, and started ad-hoc charter operations as the Red Arrow Flying Service in 1917. After "Pappy" Chalk served in the Army Air Corps in World War I, he returned to Miami and commenced scheduled service between Miami and Bimini in the Bahamas in February 1919 as Chalk's Flying Service. During prohibition, Chalk's was a major source of smuggling alcohol from the Bahamas to the United States.
Chalk's first base was a beach umbrella on the Miami shore of Biscayne Bay. In 1926 a landfill island, Watson Island, was created in Biscayne Bay close to Miami. Chalk's built an air terminal there, and operated from the island for the next 75 years. After the September 11, 2001 attacks, the company had to relocate operations due to concerns about port security. Chalk continued to be involved in the daily operations of the airline until he retired in 1975. He died in 1977 at the age of 88.