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28 Events Not to Miss This May in SWFL

Tennis tournaments, film festivals and Memorial Day celebrations traverse Southwest Florida.

BY April 21, 2023
concert crowd

Season may be coming to an end, but the Gulf Coast is alive as ever with events across the region. In Everglades City, the community gathers at city hall to commemorate Collier County’s 100th birthday this month. In Naples, comedy legend Marlon Wayans delivers laughs with a standup show. And in Punta Gorda, Irish and Scottish folk tunes resound at Celtic Fest in Fishermen’s Village. Don’t miss these stellar May events.


Now – May 21

Lobby Hero at Florida Repertory Theatre, Fort Myers

Kenneth Lonergan, known for his work on Manchester by the Sea, wrote the script for this dark comedy about an ambitious security guard in Manhattan. Broadway director Rob Lagomarsino puts on this production in the Artstage Studio Theatre.

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April 27 – May 7

Rock of Ages at TheatreZone, Naples

Set at the end of the 1980s—with plenty of spandex and Aqua Net—the jukebox musical follows a pair of star-crossed lovers and other aspiring rockstars as they band together to save their iconic music venue in L.A.’s Sunset Strip, with the sounds of Bon Jovi, Journey and other ‘80s rock gods.

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April 27 – May 14

Morning After Grace at Gulfshore Playhouse, Naples

In this production from Gulfshore Playhouse CEO and director Kristen Coury, three neighbors contemplate love, loss and relationships as they come to terms with aging in a Florida retirement community.

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April 27 – June 11

Mexico as Muse by Isabelle de Borchgrave at Naples Botanical Garden

See the Belgian artist’s paper recreations of Frida Kahlo’s as an extension of Naples Art Institute’s Miradas de Mujeres: Isabelle de Borchgrave and The World of Frida Kahlo. Some of the artist’s life-size, all-paper dresses and objects from the show are on view at Kapnick Hall through June 11. 

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May 1-7

FineMark Women’s USTA Pro Tennis Championship at Bonita Bay Club, Bonita Springs

Athletes duke it out on the court for the $100,000 prize money winnings at the elite tournament, one of only five of its kind in the country.

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May 1-31

Sunset Clouds at Phil Fisher Gallery, Naples 

The internationally recognized Naples artist displays his take on the vibrant hues of Southwest Florida’s skies through watercolor and oil paintings. 

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May 2-31

Season Closing Group Show at Harmon-Meek Gallery, Naples

The Third Street South gallery wraps its 60th season with a collection of works from its featured artists, including landscape and floral paintings by Fort Myers artist Miguel Saludes.

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May 2 – July 28

Paul Arsenault’s Reflections of Collier County: Celebrating 100 Years of Our Waterfronts at Rookery Bay, Naples

The local artist celebrates 50 years of painting in Naples with vintage pieces and works from his new For the Love of Water Collection. Some paintings from the exhibit are available for purchase, with a portion of sales supporting Friends of Rookery Bay.

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May 4-5

Latin Infusion at St. Leo Catholic Church, Bonita Springs and Carmelo’s Italian Ristorante, Punta Gorda

The five-piece ensemble—featuring soprano Erika Ramirez and baritone Fernando González—plays boleros, zarzuela pop and traditional Latin folk music as part of Gulfshore Opera’s open-air series. Watch from St. Leo’s Breezeway on May 4 or enjoy the show with dinner at Carmelo’s Italian Ristorante on May 5. 

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May 4 – Aug. 5

The Queen of Marco and the Creation of Collier County at Marco Island Historical Museum

Guests learn the story of Tommie Barfield and the role she played in building Collier County. The exhibit details her partnership with Barron G. Collier and her work lobbying in the state capital. 

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May 5-6

Naples Philharmonic Masterworks: Romeo and Juliet at Artis—Naples

The orchestra performs selections from Tchaikovsky’s and Prokofiev’s interpretations of the Shakespearean tragedy. Latvian guest conductor Andris Poga leads the group for the first time, and Macedonian pianist Simon Trpčeski accompanies the musicians for a rendition of Dmitri  Shostakovich’s famed Piano Concerto No. 2.

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May 5-7

Marlon Wayans at Off The Hook Comedy Club, Naples

The White Chicks and Scary Movie actor brings his comedy chops to Naples. Prepare for the standup show by watching his first comedy special, “Woke-ish,” on Netflix. 

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May 5-25

Divine Hypocrisy at Sidney & Berne Davis Art Center, Fort Myers

Longtime Southwest Florida artist David Acevedo examines his relationship to religion and puts forward social commentary in this mixed-media exhibit with about 35 works.

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May 5-25

Spectrum of Nature at Sidney & Berne Davis Art Center, Fort Myers

German artist Alisha Morgan draws inspiration from her worldwide travels and relationships over the years for her layered, abstract pieces in this exhibit. 

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May 6

The Orchestra at Barbara B. Mann Performing Arts Hall, Fort Myers 

Former members of the classic English rock group Electric Light Orchestra play their hits, including “Mr. Blue Sky,” backed by the Southwest Florida Symphony. 

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May 6

Old Dominion at Hertz Arena, Estero

The five-time, Country Music Award-winning band showcases its contemporary country-rock sound on its No Bad Vibes tour.

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May 8

The Commemoration of the Collier County Centennial, Everglades City

Join county commissioners on the historic steps of Everglades City Hall to celebrate the county’s 100-year anniversary. Later this summer, Collier County Museum opens a time capsule in honor of the first Board of County Commissioners meeting.

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May 8-30

Lisett Llorens at Marco Island Center for the Arts

The Bolivia native uses her educational background in fashion and jewelry design to her intricately detailed pieces full of Latin America’s flora and Hispanic architecture as part of Collier County’s ¡ARTE VIVA! celebration of Spanish and Latin art.

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May 8 – July 3

The Artist’s Question … Answered in Fiber at Marco Island Center for the Arts

Studio Art Quilt Associates’ members from around the country exhibit elaborately stitched pieces. Juror Zak Foster selected 29 quilts that answer questions asked by the artists.

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May 11-14 & 18-21

Stage It! Ten-Minute Play Festival at Centers for the Arts Bonita Springs

Hundreds of playwrights from all over the world submit for the annual juried festival, where no production lasts more than 10 minutes. Patrons of the event vote for an Audience Favorite play, so be sure to see more than one.

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May 12-14

ELVIS: In Person at The Bell Theatre, Cape Coral 

Graceland ranked Florida’s 19-year-old Matt Stone in the top 10 of their 2022 list of Elvis tribute artists. The teenager breathes new life into The King’s vocals, gyrations and overarching stage presence.

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May 13

Celtic Fest at Fishermen’s Village, Punta Gorda

Bagpipes and fiddles provide instrumentals for traditional and modern spins on Scottish and Irish tunes from Eireann’s Call, Mac Tier and more Celtic bands. Plus, Kellyn Celtic Arts dancers showcase their skills.

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May 17

Ride of Silence at Cambier Park, Naples

During National Bike Month, Naples Pathways Coalition joins the global organization’s annual silent ride around the park  to honor people who have suffered injuries or been killed while cycling. 

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May 17-21

Fort Myers International Film Festival

Sidney & Berne Davis Art Center and other venues throughout the city roll out the red carpet for indie film screenings, filmmaker panels, performances and parties. Flicks include the Deep Rising ocean-mining documentary narrated by Jason Momoa and the feature film Other People’s Children depicting one woman’s maternal relationship with her boyfriend’s daughter. 

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May 19

Eli Young Band at Seminole Casino Hotel Immokalee

Since its debut at the University of North Texas in 2000, the modern country group has won four Billboard No. 1 hits and toured with legendary acts, like Toby Keith, Tim McGraw and Rascal Flatts. 

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May 20-25

The 25th Annual Putnam County Spelling Bee at Gulfshore Playhouse, Naples

Steven Calakos directs this production of the Tony Award-winning musical, where students take the stage and put their vocabularies to the test.

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May 25-26

Patriotic Pops at Artis—Naples 

Kick off Memorial Day Weekend with the Naples Philharmonic, Naples Philharmonic Chorus and Naples Philharmonic Youth Chorus for the annual salute to the red, white and blue. Radu Paponiu conducts the symphony in this performance, featuring the music of iconic American composers John Philip Sousa and Irving Berlin. 

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May 26

Brit Floyd: 50 Years Of The Dark Side Of The Moon at Hertz Arena, Estero

The fan-favorite tribute band returns to the stage to celebrate Pink Floyd’s iconic album, Dark Side of the Moon, recreating the band’s final 1994 tour. The group has played more than 1,000 shows worldwide since its beginnings in 2011. 

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