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20 Things to Do to Make Your September More Eventful

Art exhibits, music festivals and comedy shows round out the month.

BY August 30, 2023
Island Hopper Songwriter Fest
Island Hopper Songwriter Fest (Photo by Brian Tietz/ Courtesy of Lee County Visitor & Convention Bureau)

When you look at the calendar for Southwest Florida goings-on, it becomes abundantly clear local arts and entertainment know no off-season. In Estero, famed country music star Thomas Rhett brings his twang to Hertz Arena. In Fort Myers, a juried art show honors local artists on the one-year anniversary of Hurricane Ian at Alliance for the Arts. And across the region, the three-county Sizzle Dining’s SWFL Restaurant Week ignites the culinary scene. Don’t miss these September events.


Now – Sep. 10

Frida and Her Garden at Naples Botanical Garden 

Here is your last chance to view a colorful traveling exhibition, which brought to the garden a recreation of late Mexican artist Frida Kahlo’s Casa Azul home in January. In its garden setting, the exhibition demonstrates how plants inspired the seminal artist’s work. Six oversized animal sculptures tower 8-plus feet and bear folk art totems that also influenced Frida. Visitors can readily identify most of the animals, but if the unusual hairless Mexican dog stumps you, it’s known as Xoloitzcuintli.

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Now – Sep. 16 

Agatha Christie’s Murder on the Orient Express at Broadway Palm, Fort Myers

Glamour, intrigue, suspense, humor: Broadway Palm fuels this train ride with all that and more. “We remain true to the intent of the script from Ken Ludwig’s wonderful adaptation of the classic Agatha Christie’s mystery,” says director Dean Sobon. Pair this with the production’s modern technical enhancements, and Dean says audiences have a compelling ‘whodunit’ on their hands.

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Now – Oct. 15

Naples Invitational at Naples Art Institute

Showcasing the talent of 40 contemporary Naples artists, the biennial survey reflects the complexities and opportunities of the American experience today. The show is dedicated to ceramic artist Gaily Geary, who passed away during the first week of the exhibition. Her three included pieces demonstrate the unique graphic expression that made her work part of collections across the United States. 

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Now – Oct. 27 

2023 Summer II Exhibition at Rookery Bay National Estuarine Research Preserve, Naples

Friends of Rookery Bay and United Arts Collier partner for their summer exhibition of juried, wide-spectrum works from 30 Florida artists. In keeping with Rookery Bay’s mission to connect people with local coastal environments, the art represents a wide variety of materials, including oil, acrylic, photography, digital paint, and mixed media. All art is for sale.

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Sep. 1 – 30

Storm Stories: A Juried Exhibition at Alliance for the Arts, Fort Myers 

The juried visual art exhibition debuts in tandem with a year-long oral history project to express the impact Hurricane Ian had on the lives of local artists. Meant to heal our souls, the artworks incorporate objects found after the storm. The oral-history project results in Storm Stories—Hurricane Ian: Stories of Survival, Heroism, and Humanity, a book full of prose and poetry documenting people’s accounts of the disaster. The book releases this month, and the exhibition’s closing reception coincides with Ian’s first anniversary.

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Sep. 2 – Apr. 7

Tamara Kostianovsky: Botanical Revolution at Artis—Naples, The Baker Museum 

Israeli by birth and raised in Argentina, Tamara Kostianovsky’s world vision now hones in on the Southwest Florida environment with her first-floor exhibition at The Baker Museum. Through her signature use of repurposed textiles in dynamic sculptures, she weaves together the human-organic connection. This, her first exhibition in the Southeastern U.S., debuts new works referencing local bird and plant life, such as her newly created three-panel piece titled Morning Walk at Corkscrew Swamp, inspired by the sanctuary’s vibrant ecosystem. 

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Sep. 7 – 27

Sizzle Dining’s SWFL Restaurant Week, throughout Lee and Collier counties

With a record number of establishments on the docket this year—more than 90 throughout Lee, Collier and Charlotte counties—here’s your chance to support the hospitality industry when it needs it most. One menu stands out not only for its mouthwatering dishes but because giving Cielo a Sizzle try also means supporting business on Sanibel Island, whose restaurants still suffer heavily from Hurricane Ian’s aftermath. Think about it: brown butter-bourbon salmon or apricot-pistachio seared chicken and chocolate almond truffle cake with a side of feel-good for helping one of the island’s best survive.

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Sep. 8

Intocable Concert at Charlotte Harbor Event and Conference Center, Punta Gorda

Born from northern Mexican and southern Texan border cultures, the Tejano/Norteño sounds of the award-winning touring group have captivated fans since the 1990s. Their recordings have reached the top 10 on the singles charts and won Grammy Awards, Billboard Regional Mexican Awards and Latin Grammy nominations.

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Sep. 8 – 10

Chris Kattan at Off the Hook Comedy Club, Naples

From TV to the big screen, Chris Kattan has made his name in comedy circles on sitcoms, Saturday Night Live and spinoff flick A Night at the Roxbury with Will Ferrell. At Off the Hook, he has become one of the audience’s favorite showmen with his sassy delivery and undeniably hysterical characters.

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Sep. 8 – Oct. 1

Noises Off at Laboratory Theater, Fort Myers 

A play about producing a play, this show follows the slapstick antics as a suggestive comedy makes its way to the stage. The farce deals with an ineffective director, alcoholism and love triangles among the cast. Physical comedy and a dazzling range of British dialects add dimension to the always-cunning performances Lab Theater pulls off from its small stage. 

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Sep. 9

Tunnel to Towers 5K, Fort Myers 

The Tunnel to Towers Run & Walk Series honors all who lost their lives that day and supports first responders and the military in the line of duty. In its sixth year, the Fort Myers rendition starts and ends at Florida SouthWestern State College. 

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Sep. 14 

Thomas Rhett at Hertz Arena, Estero 

Slotted as a top country singer and songwriter, Thomas Rhett admits the rock and hip-hop he grew up on also seep into his repertoire. Son of musician Rhett Akins, the Academy of Country Music award-winner has music in his blood. Nate Smith Music and Cole Swindell play warm-up on the “Home Team” tour, celebrating the cities and folks Thomas plays to and parties with.

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Sep. 15 – 17

New Works Festival at Gulfshore Playhouse, Naples 

In its final season at its original theater before moving to Gulfshore’s new home, the 10th-annual New Works Festival stages three winners from a months-long judging process, each followed by post-show talkback opportunities and staged readings. The three winning titles—Circle Forward, The Lion Tamer and Hrzda—join one of the 2023-2024 season’s plays, The Refugees, for the festival and its interactive workshops. 

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Sep. 16

Fort Myers Latin Music Festival at Caloosa Sound Amphitheater, Fort Myers

Established Latin artists like popular Cuban singer and songwriter Osmani Garcia—known for his catchy and upbeat reggaeton and Latin pop music—join established and up-and-coming Florida performers, including Miami-based Lucy Grau, dubbed the ‘Latin Disco Queen.’ Hispanic culinary specialties, bounce houses and cultural activities make this an all-day, riverfront fiesta for the whole family.

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Sep. 19 – Oct. 29

Beguiled Again at Florida Rep, Fort Myers 

Rogers and Hammerstein may strike a chord, but Rogers and Hart? This revue of the beautiful music Richard Rogers and lyricist Lorenz Hart once made together kicks off Florida Rep’s 26th season while it brings back memories and stirs nostalgia. “Bewitched,” “The Lady is a Tramp,” “Where or When,” “My Funny Valentine:” Just a few favorites woven into light, music-driven narrative as a vehicle into the past.

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Sep. 20

Nurses Night Out with Greg Williams at Snappers Comedy Club, Fort Myers

From male nurse to stand-up comedian, Greg “G” Williams has his audience in stitches with tales from real-life hospital experiences flipped to expose the humorous side of the medical profession. All jokes aside, G dedicates his shows to those working to save lives and provide comfort. 

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Sep. 22 – Oct.1

Island Hopper Songwriter Fest, Lee County

The eighth-annual festival—featuring headliners Kristian Bush of Sugarland and Grand Ole Opry artist Chris Janson—expands its musical dynamics to one additional community this year. Cape Coral joins Captiva Island, Fort Myers Beach and Downtown Fort Myers on the festival’s tuneful journey. Cape waterfront venues Gather, High Tide Social and Nauti Mermaid Dockside Bar & Grill host the Sep. 25-26 portion of this year’s festival, while other venues throughout the county celebrate their comeback to the scene following Hurricane Ian recovery efforts.

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Sep. 23 

Key Lime & Tropical Fest at Fishermen’s Village, Punta Gorda 

In its 10th year, the festival celebrates all things tartfully key lime and artfully tuneful. Tropical Avenue Band headlines from the beach adjacent to Fishermen’s Village Tiki Bar. Simply Sweet shop fills the zesty niche with tasty treats from key lime pie and fudge to taffy and pie on a stick. 

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Sep. 28

Zach Bartholomew Trio: Chick Corea Tribute at Center for Performing Arts’ Moe Auditorium & Film Center, Bonita Springs

Award-winning musician Dr. Zachary Bartholomew pays tribute to one of jazz history’s most iconic pianists and composers, the late Armando “Chick” Corea. Zach has headlined at top jazz venues and performing arts centers around the country and performed at festivals globally. In addition to showcasing Chick’s prolific work, Zach features some of his original compositions paying homage to the musical legend.

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Sep. 28 

Mary Chapin Carpenter & Shawn Colvin at Seminole Hotel & Casino, Immokalee 

Longtime friends, the two Grammy Award-winning artists share experiences, music and the stage on a co-headlining tour that kicks off at Seminole Center. They revisit biggest solo hits like Carpenter’s “Passionate Kisses” and Colvin’s “Steady On,” while reliving stories from their illustrious careers as country and folk music icons. 

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