- Wednesday, September 12 – Pensacola-based pianist Bobby van Deusen, a boogie-woogie, ragtime and stride piano marvel with equally strong classical chops, performs at a preseason fundraiser for the Charlotte County Jazz Society. JD's Bistro, Port Charlotte. 2 p.m.
|Lisa Kelly, J.B. Scott|
- Monday, October 8 – Singer Lisa Kelly and trumpeter J.B. Scott open the Charlotte County Jazz Society’s 2018-19 concert season. William H. Wakeman III Theater, Cultural Center of Charlotte County. Port Charlotte. 7 p.m.
- Thursday to Sunday, October 18-21 – 39th Clearwater Jazz Holiday, once again a jazz event in name only. Most headliners are from genres other than jazz. Coachman Park.
- Wednesday, October 31 – Vibes player Joe Locke guests with the Naples Philharmonic Jazz Orchestra in the sextet’s 2018-2019 season opener. Artis-Naples’ Daniels Pavilion, Naples. 6 and 8:30 p.m.
- Monday, November 12 – Trombonist Bill Allred’s Classic Jazz Band performs in the Charlotte County JazzSociety’s concert series. William H. Wakeman III Theater, Cultural Center of Charlotte County. Port Charlotte. 7 p.m.
- Friday to Sunday, November 16-18 – The 28th annual Suncoast Jazz Festival offers a mix of Swing, big band, blues and traditional jazz. Headliners include Adrian Cunningham, Nate Najar, Chuck Redd and Rossano Sportiello.Clearwater Beach.
- Friday, November 23 – Saxophone smoothie Dave Koz brings the 2018 edition of his Christmas Tour, with Mindi Abair, Jonathan Butler and Keiko Matsui, to the area. Van Wezel Performing Arts Hall, Sarasota. 8.p.m.
- Sunday, November 25 – Saxophone smoothie Dave Koz brings the 2018 edition of his Christmas Tour, with Mindi Abair, Jonathan Butler and Keiko Matsui, to Artis-Naples’ Hayes Hall. Naples, 7 p.m.
- Wednesday, November 28 – Guitarist Romero Lubambo guests with the Naples Philharmonic Jazz Orchestra in the sextet’s 2018-2019 concert series. Artis-Naples’ Daniels Pavilion, Naples. 6 and 8:30 p.m.
Several local restaurants (including J.D.’s in Port Charlotte, 88 Keys Florida and The Blue Turtle in Punta Gorda, Fandango in Sarasota, The Roadhouse and The Barrel Room at Twisted Vine Bistro in Fort Myers, and Slate’s in Cape Coral, offer jazz steadily). A variety of matinee concerts sponsored all season by the Jazz Club of Sarasota and the South County Jazz Club also keep things swinging for jazz lovers.