Southwest Florida’s Entertainment Calendar Packed With Music, Arts, and Holiday Shows

Music, laughs, and art fill Southwest Florida's upcoming season. From September 2025 through April 2026, more than 50 events will draw crowds to venues across the region. The Island Hopper Music Festival starts the fun this week with Chris Young and LOCASH taking the stage.

Now in its 11th run, Island Hopper starts Sept. 24 in downtown Fort Myers. The music moves to Fort Myers Beach Sept. 26-28 as the Westin Cape Coral Resort hosts LOCASH's performance. At Pink Shell Beach Resort, Chris Young will turn a pool party into an unforgettable show.

Off The Hook Comedy Club welcomes Billy Gardell for six shows Sept. 26-28, and Nate Jackson's Big Dog Tour stops at Barbara B. Mann Performing Arts Hall on Sept. 27.

Fans of scary stuff can check out Florida Horror-Fest on Sept. 28. Special guests include Paul T. Taylor from Hellraiser: Judgment and Dr. Chud, who was the drummer for the Misfits.

The Naples Players presents two October productions: Agatha Christie's And Then There Were None, plus Ada and the Engine by Lauren Gunderson. Broadway Palm brings Pretty Woman to audiences from Oct. 3 through Nov. 15.

Winter fun starts with Marco Island's first Old World Christmas Bazaar Market at Veteran's Park, November 29-30. Sand artists return to Fort Myers Beach Nov. 20-24 for the 35th American Sand Sculpting Championships.

Live Fest marks its sixth year on Dec. 13 at Tiburon Golf Club. Darius Rucker tops the bill, with Rock Republic and American Idol star Casey Bishop rounding out the show.

Marco Island Center for the Arts unveiled its 2025-26 theater schedule through April. Shows include California Suite, Four Old Broads,  and Moonlight and Magnolias. 

Most shows have tickets on sale now at their venues. While many Island Hopper shows are free, Chris Young and LOCASH tickets range from $35 to $65.