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