WAIL995

WAIL (99.5 FM) is a commercial radio station broadcasting a classic rock format, licensed to Key West, Florida, and serving the Florida Keys. The station is currently owned by Fiorini Keys Media, LLC, following a succession of ownership changes over the years. WAIL was formerly known as "99.5 The Whale" and previously simulcast with sister station WFKZ (103.1 FM) under the joint brand "99.5/103.1 Sun FM." Clear Channel Communications placed the station into the Aloha Stations Trust in 2008 as part of a divestiture required to comply with ownership caps following a leveraged buyout. Florida Keys Media, LLC acquired WAIL and three sister stations from the trust for $650,000 in February 2014, and the station was subsequently sold again to Fiorini Keys Media in July 2024. WAIL continues to simulcast programming with WFKZ during select dayparts, including an afternoon program and Saturday night programming featuring The Night Train With Joey Naples, maintaining the longstanding radio relationship between the two Florida Keys frequencies.