The Latest

24 May Events in SWFL

Art exhibits, Cinco de Mayo parties and traveling basketball troupes make a splash this month.

BY May 2, 2024
Sidney & Berne Davis Art Center Courtesy © The Lee County Visitor & Convention Bureau.

Celebrate all Southwest Florida has to offer in style this May. On Marco Island, The Naples Players presents a bilingual adaptation of one of William Shakespeare’s classic comedies. In Bonita Springs, the Finemark Women’s Pro Tennis Championship brings on-the-rise talent to the Gulf Coast. And Fort Myers’ Fringe Festival offers edginess and ingenuity to the River District. Don’t miss these May events. 


Now through May 5

FineMark Women’s Pro Tennis Championship at Bonita Bay Club

Watch some of tennis’ top up-and-coming players battle it out in singles and doubles matches for a chance to win the $100,000 purse. USTA Pro Circuit often serves as a stepping stone to greater success—past competitors include Lauren Davis, Katie Volynets and rising star Coco Gauff. Learn More


May 1-15

Paint the Town with Joy! at East West Fine Art, Naples

Joy Stanley’s colorful works pay homage to locally loved institutions—Naples Pier, Bleu Provence, The French Brasserie Rustique—recreated with a whimsical sensibility. See the artist’s watercolors at the East West’s Mercato location. Learn More


May 1-19

The Naples Players present Clue: On Stage at Naples United Church of Christ

In this classic ‘whodunit,’ Mr. Boddy turns up dead at his own dinner party. The familiar characters, brought to life by Naples Players actors, are all suspects. The production marks the last of the theater company’s performances at Naples United Church of Christ before they move to their new home. Get Tickets 


May 2 

The Harlem Globetrotters 2024 World Tour at Hertz Arena, Estero

Catch the slam dunks and rapid dribbling of the beloved basketball team as they match up against rivals, the Washington Generals. Don’t think you’re off the hook—keep an eye out for the new Halftime Skills Showcase, where lucky fans find themselves competing on the court. Get Tickets


May 2-5

PlayLab 2024 Festival of New Works at Florida Repertory Theatre, Fort Myers 

Actors, directors and playwrights debut five new play readings at the weekend festival. Keep your eyes peeled for a romantic comedy about modern-day matchmaking and a dramedy about loneliness and loss. Don’t miss the playwrights’ roundtable discussion on May 5 after the final play reading. Get Tickets 


May 3-5

Hibiscus Festival at Gilchrist Park, Punta Gorda

The “City of Hibiscus” floods the park overlooking the Peace River for its 20th anniversary celebration. The festival kicks off with a Friday evening concert, with live music from about 20 groups serenading the party all weekend. Check out the plant sales and food and drink vendors between sets. Learn More


May 3-19

The Studio Plays present Doubt: A Parable at Golden Gate Community Center, Naples

John Patrick Shanley’s Pulitzer Prize- and Tony Award-winning drama involves the ethical dilemmas that unfold when the strict principal of a Catholic school suspects the popular priest of having inappropriate relations with a student. This production has a 16-and-up rating for references to sexual abuse and adult content. Learn More


May 3-30

Divergent Inspiration at Sidney and Berne Davis Art Center, Fort Myers

STARability Foundation members showcase their skills in this inclusive, space-themed art exhibit. The Naples-based nonprofit provides services to people with intellectual or developmental disabilities, and the exhibition explores how everyone’s brains function in vastly unique and divergent ways. Learn More 


May 4

National Estuaries Day 2024 at Rookery Bay Environmental Learning Center, Naples

Rookery Bay joins the country’s 30 national estuarine research reserves for a day of exploration. Get on the water with kayak demos and boat rides, tour the facility’s nature and wildlife exhibits and art gallery, and feast on food truck bites. Learn about Rookery Bay’s sea turtle and shorebird monitoring, shark and water-quality research, and local natural and human history. Learn More 


May 4 and 5 

Cinco de Mayo Bar Crawl, Fort Myers

Kick-start the holiday fun early at The Hideaway Bar on May 4. Visit your favorite bars and pubs of the River District, sipping on themed pours like a Chelada beer cocktail at Main Street’s Indigo Room. Munch on tacos at select locations. Learn More


May 4

La Comedia of Errors at Arts Center Theatre, Marco Island

The Naples Players present a 90-minute bilingual adaptation of one of William Shakespeare’s funniest comedies. In the play, two sets of twins are mistaken for each other, and crazy antics ensue. Learn More


May 4 — July 28

Tradition Interrupted at The Baker Museum, Artis–Naples

A dozen national and international artists explore their ancestral connections as they merge ancient art and craft customs with innovative techniques. See interpretations ranging from woodcut prints and photo-weaving to Coca-Cola can sculptures. Learn More


May 6 — July 2

Fiberlicious: A Textile Lover’s Feast at Marco Island Center for the Arts

Fort Myers-based Art Quilters Unlimited presents distinct, woven works, including wearable items with layered textures. Works demonstrate hand and machine stitching techniques, fiber manipulation, burning, printing, weaving, embellishing, felting, dying and beading. Learn More 


May 7 

Indigo Girls at Barbara B. Mann Performing Arts Hall, Fort Myers

The folk rock duo made a splash on their debut album with the iconic song “Closer to Fine.” Thirty-five years later, Emily Saliers and Amy Ray are still performing, now touring with their latest album, Look Long. Critics hail the album for its diversity, with tracks touching on politics and culture—from gender identity to good old Southern living. Get Tickets


May 11

Day Before Mother’s Day 5K, Fort Myers Beach

Kick up some sand as you take on the beach race course.  Take off at Times Square, head south past Margaritaville Resort, then circle back to Bowditch Park before ending the race back where you started. Learn More


May 15-25

Men Are Dogs at Fort Myers Theatre

In this comedy, therapist Dr. Cecelia Monahan uses unorthodox methods to run a support group for single and divorced women until a chance encounter with a substitute delivery man makes her reevaluate her own experiences. Stick around for a ‘talk back’ session with playwright and director Joe Simonelli following the opening night performance. Learn More


May 16-18

New Play Contest at The Laboratory Theater of Florida, Fort Myers

In this annual competition, three playwrights vie for The Louise Wigglesworth Excellence in Playwriting Award. Catch readings of the new works written by playwrights from around the country. Learn More 


May 18

Day of Celtic Music at Fishermen’s Village, Punta Gorda

The Cultural Heritage Center of Southwest Florida and the New World Celts, Sarasota Chapter, bring national talent to the Gulf Coast in this annual festival. Enjoy performances at the Sunset Beach Club and Center Court, including McIntyre Band and Celtic Conundrum. Learn More


May 18

Brave New Pops 3: ’70s, ’80s, ’90s Unplugged at Barbara B. Mann Performing Arts Hall, Fort Myers

Multi-instrumentalist Andrew Lipke has worked with the revolutionary composer Steve Hackman (known for creating And I Love Her: The Beatles Reimagined orchestra show) and Led Zeppelin tribute band Get The Led Out for more than a decade. See him join the Southwest Florida Symphony for a set of symphonic, reimagined rock classics by artists like Nirvana, Eric Clapton, Paul McCartney and Rod Stewart. Learn More


May 22-26

Fort Myers Film Festival 

Hundreds of local and national independent flicks take over Fort Myer for five days of movie-loving magic. Don’t miss out on mingling with the filmmakers at the red carpet opening on May 22 at Sidney & Berne Davis Art Center. Learn More 


May 23 and 24

Patriotic Pops at Artis—Naples

Get into the Memorial Day spirit as the Naples Philharmonic, Naples Philharmonic Chorus and Naples Philharmonic Youth Chorus salute our troops in this star-spangled performance. The show pays tribute to the country’s musical heritage, featuring the best-loved works by American composers. Vocalist Nikki Renée Daniels, star of the recent Broadway revival of Company, makes a guest appearance. Learn More 


May 23 — June 2

Into the Woods at Cultural Park Theatre, Cape Coral

The Stephen Sondheim classic weaves together several Brothers Grimm fairy tales as the Baker and his wife, Cinderella, Red Riding Hood and other fairytale friends meet in an enchanted forest and set out to break a witch’s curse. Learn More


May 30 — June 2

Fringe Fort Myers 2024

Provocative, uncensored and inclusive live performances take over Alliance for the Arts and Broadway Palm Dinner Theatre for a festival celebrating everything alternative, edgy and refreshingly offbeat. Festivities kick off with the Teaser Show, where each group has three minutes to sell the audience on their show. Nearly 50 performances play on three different stages throughout the four days. Check the ratings before you go: Some performances are billed for mature audiences only. Learn More


May 31

Billy Currington at Seminole Casino, Immokalee

The Grammy Award-nominated singer-songwriter takes the outdoor stage with his smooth, distinctive voice and award-winning country hits. Get Tickets 

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