WAIL (99.5 FM) is a radio station broadcasting a classic rock format.
[2] On January 25, 2008, it was announced that WAIL-FM was one of several Clear Channel radio stations to be sold, in order to remain under the ownership caps following the sale of Clear Channel to private investors.
WAIL simulcasted with WFKZ, and the two stations were formally known as "99.5/103.1 Sun FM."
The trust sold WAIL and three sister stations to Robert Holladay's Florida Keys Media, LLC for $650,000; the transaction was consummated on February 28, 2014.
In July 2024 the station was sold to Fiorini Keys Media, LLC WAIL simulcasts on WFKZ during the Hoebee In The Afternoon Experiment, M-W 2–6, TH2-7 and Fri 2–6.