The station signed on the air in December 1960; 63 years ago (December 1960). Its original call sign was WYND. It was owned by Kelsey Hutchinson of Gulf Coast Broadcasting.[4] On November 1, 1966[5] it switched to a top 40 format called Surf Row Radio. It has had different call letters over the years, including WWZZ and WSGX. As WSGX, the station was broadcasting in AM Stereo.[6] In 2011, the station became a Fox Sports Radionetwork affiliate.
In October 2013, the station changed to adult standards and big band hits. The on-air staff included Eugene Dolan, Doug Miles, Smilin' Lou Powers, with shows such as "Big Band Wakeup Call", "Sunshine Music Memories with Smilin' Lou Powers", "Big Band Files with Doug Miles", "The Sounds of Sinatra with Sid Mark", "Milkman's Serenade" with Eugene Dolan, "Those Were the Days" with Danny Lane, "Swing Street" with Kevin Hayes, Artist Spotlight with Doug Miles, contributor Don Henderson, "Your Hit Parade" with Bea Wain and Andre Baruch, and Old Time Radio Classics with Will Rogers. Betty Comora was Creative Director.
"Artist Spotlight with Doug Miles" guests include: Cynthia Sayer, Liz Callaway, Dick Hyman, Patti LuPone, Steve Lawrence, John O’Hurley, Jack Jones, Sandy Stewart, Judy Carmichael, Linda Purl, Sid Mark, Audrey Landers, Deana Martin, Larry Kane, Mark Russell, Stephanie Trick, Kitt Moran, Julie Budd, Ann Hampton Callaway, Dennis Bono, Michael Feinstein, Sarasota Jazz Project Big Band, Ken Loomer Big Band, and Ocean's Eleven Big Band.
On August 8, 2016, the station was sold by Southwest Florida Radio Broadcasting LLC to Solmart Media for $125,000. The format was changed to Spanish language programming, simulcasting then-sister station WZZS in Zolfo Springs, Florida. Eventually, WTMY began airing its own Regional Mexican format. On April 4, 2019, the station added an FM translator, W256DI on 99.1 MHz.