December is the time for community, festivities and cooler weather. Along with a bounty of holiday festivities, Southwest Florida offers plenty of activities to keep you entertained. In Punta Gorda, Fishermen’s Village comes to life with its nightly Festival of Lights, Fort Myers’ Florida Repertory Theatre presents two theatrical shows to delight, country stars fire up the night at Hertz Arena to benefit Hurricane Ian relief efforts, and Naples’ Paradise Coast Sports Complex brings winter to the coast with its SnowFest. And, there’s more theater, art and merrymaking to make the last month of the year your best one yet.
Now – Dec. 18
Agatha Christie’s And Then There Were None at Florida Repertory Theatre, Fort Myers
In this whodunnit thriller, a host invites 10 strangers to an island, where one of the guests turns up dead. Follow along with the show’s two possible conclusions, as the theater alternates endings throughout the production’s run.
Dec. 1
Boots on the Sand: Hurricane Ian Benefit Concert at Hertz Arena, Estero
Don’t miss this star-studded lineup of musicians as they come together to support the Gulf. Lynyrd Skynyrd, Gavin DeGraw and Brian Kelley (formerly of Florida Georgia Line) are just a few of the artists headlining the night, with comedian Jim Bruerer hosting. All proceeds benefit disaster relief through Volunteer Florida and the Community Foundations of Southwest Florida.
Dec. 1-4
Naples Fun Festival at East Naples Community Park
Pickleball enthusiasts convene in this age 50-plus tournament sanctioned by USA Pickleball. On the court, players get a mix of fun and fierce with Glow in the Dark play and tournament-level competitions. And off the court, pickleball coach Rachael Kroog brings leads a daily variety show packed with her pickleball ukelele, plus yoga, music and drinks to keep your mind and body fed.
Dec. 2
John Mulaney at Hertz Arena, Estero
The former Saturday Night Live cast member is back on tour. The two-time Emmy Award winner’s “From Scratch” tour has sold out arenas across the country.
Dec. 2
Off The Walls, Center for the Arts Bonita Springs
Everybody takes home an artwork, trip or other experience at this event at Center for the Arts Bonita Springs. Your entry ticket—which includes snacks, drinks and live entertainment—enters you to win any of the artworks on the wall or a curated experience, drawn through a random raffle. The event raises funds for scholarships for local kids.
Dec. 3
Collier County SnowFest at Paradise Coast Sports Complex, Naples
The 38th annual festival features nearly 100 tons of snow (from cubes run through a chipper for a life-like effect), plus ice skating, bounce houses, a holiday train and a screening of Will Ferrell’s Elf on a 32-foot screen on the complex’s lawn. Kids can expect a visit from Santa.
Dec. 6
The Commodores at Artis—Naples
The legendary funk band (sans Lionel Richie) plays their greatest hits at Hayes Hall. With more than seven No. 1 singles and five No. 1 albums, the Motown Band is sure to put you in a groovy mood.
Dec. 6-27
Cloud Tree at East West Fine Art, Naples
Russian surrealist Stanislav Plutenko merges space and time in his vibrant allegorical and fantasy paintings. The painting draws inspiration from the children’s book The Little Prince, exploring the idea of protecting the tiny planet we call home.
Dec. 6-31
Small Works of Art at Harmon-Meek Gallery, Naples
Shop from hundreds of small paintings and sculptures—perfect for holiday gifting. The gallery’s annual event showcases pieces from some of its nearly 30 represented artists, including Richard Segalman and Hunt Slonem.
Dec. 8
Frankie Valli and the Four Seasons at Barbara B. Mann Performing Arts Hall, Fort Myers
The 1960s group plays some of their greatest singles, like “Big Girls Don’t Cry” and “December ’63 (Oh What a Night).” The band has sold more than 100 million records and promises an unforgettable performance—even if your name isn’t Sherry.
Dec. 9
Brews for the Birds at The Wonder Gardens
Local breweries, food trucks and live music fill the Bonita Springs botanical garden and animal refuge. Proceeds benefit rehabilitation and care for The Wonder Gardens’ resident birds.
Dec. 10
Live Fest Presented by QBE Shootout at The Ritz-Carlton Golf Resort, Naples
After the tournament, Tiburón’s driving range transforms into a stage for Live Fest, headlined by country music star Brad Paisley, with Jake Owen and .38 Special. Proceeds benefit local nonprofits to help provide hurricane relief.
Dec. 10
Naples Fall Classic Half Marathon & 5K at Sugden Regional Park
As the seventh stop on the South Florida Half Marathon Tour, this race, with two courses, takes runners through Naples’ waterfront communities. The half-marathon course and 5k course loop around Sugden Regional Park, and the 13.1-mile race extends to East Naples and Isles of Collier Preserve. All runners end with a chorus of cheers at the park’s stadium amphitheater by Lake Avalon.
Dec. 10
Reba McEntire at Hertz Arena, Estero
The country artist, known for hits like “I’m a Survivor” and “Consider Me Gone,” performs in Estero. All tickets purchased for the original November date will be honored.
Dec. 11
Rock the Stage Fest Finals at Alliance for the Arts, Fort Myers
A local version of Battle of the Bands plays out at Alliance for the Arts as 10 finalists (with adult and under-18 divisions) face off for prizes, including scholarships and recording sessions with music producer Chris Moon. There’s more music on tap for the day, too, with headliners KISS Alive, a KISS tribute band and Shoot to Thrill, an AC/DC cover group.
Dec. 12
Big Bad Voodoo Daddy at Caloosa Sound Amphitheater, Fort Myers
The throwback swing group performs at the new Caloosa Sound Amphitheater in Centennial Park as part of Luminary Hotel & Co.’s free Rockin’ on the River concert series. Doors open at 6 p.m. for the swing band, which performs a combination of holiday originals and classics.
Dec. 16 – Jan. 15
Freud’s Last Session at Florida Repertory Theatre, Fort Myers
In this two-man show, psychoanalyst Sigmund Freud meets author and born-again Christian C.S. Lewis for an intellectual debate about love, God and the meaning of life. Maureen Hefferman—who has more than 90 directorial credits to her name—heads this production.
