May in Tampa Bay is where sunshine meets celebration. As the days get longer and the weather hits that sweet spot, the city comes alive with outdoor festivals, waterfront fun, live music, and experiences that invite you to slow down—or turn it all the way up. From neighborhood happenings to major events, May is the perfect time to get outside, try something new, and soak in everything that makes Tampa Bay shine.
May 4-11
Visitors are invited to get a closer look under the hoods at Tampa Bay Automobile Museum’s most popular event, Hoods Up! This experience showcases a unique blend of vintage vehicles alongside more modern, electrically powered cars, giving guests a rare opportunity to explore the craftsmanship, innovation, and history behind the museum’s remarkable collection.
May 10
Celebrate Mother’s Day in style with a stunning cruise around the bay aboard Yacht StarShip. Treat Mom to an exquisite buffet crafted by executive chefs, enjoy the lively atmosphere with a live DJ on the top deck, and take in the breathtaking views of Tampa Bay. It’s a beautiful way to honor the incredible woman you call Mom.
March 6-May 10
Encounter new flavors at the Busch Gardens Food and Wine Festival, returning once again this year. Enjoy a delicious menu of food and drinks that are as dynamic and unique as the park itself. Guests are encouraged to sip and savor their way throughout the whole weekend!
May 9
The Tampa Bay Sun are celebrating YOU, their loyal fans! Join the Sun for their final home game as Tampa Bay Sun FC takes on Dallas Trinity FC on Fan Appreciation Night. The Sun are pulling out all the stops to thank the best fans in the league, so come out for a night of soccer, surprises, and Sun spirit!
May 16
Mr. World Wide is bringing the heat to Tampa Bay as part of his “I’m Back” Tour. Fans can expect an electrifying night packed with global hits, nonstop energy, and that signature Pitbull party vibe. If you’re looking for a reason to turn up this spring, this is one show you won’t want to miss.
May 16-17
Tampa City Ballet presents The Sleeping Beauty, a stunning ode to classical ballet that will sweep audiences into a world of enchantment. Featuring iconic choreography from Rose Adagio, this dazzling production at the New Tampa Performing Arts Center offers an unforgettable theatrical experience with romance and timeless beauty.
May 17
Chicken Yoga is a playful, all-levels flow with Yoga Loft Tampa benefiting Ybor Misfits Microsanctuary—blending movement, breath, and a little unexpected fun. Practice alongside feathered friends in a lighthearted, grounding experience that’s uniquely Ybor. Bring your mat, an open mind, and stay after to sip and spend extra time with the chickens. All proceeds support the care of Ybor’s beloved residents. (Tip: leave shiny jewelry at home—the chickens can’t resist!)
May 17
Join the Yuengling Draft Haus & Kitchen for a fun-filled Kids Market at Yuengling Family Day. Young entrepreneurs ages 5–17 will be running their own booths, selling everything from handmade crafts to sweet treats and creative games. It’s a great opportunity for kids to learn business skills, build confidence, and showcase their talents. Families are invited to enjoy the festivities and support these amazing young vendors. Interested in having your child participate as a vendor? Be sure to register early—spots fill up fast!
May 21
Local market in the heart of Seminole Heights District, held every 3rd Thursday at Common Dialect brewery, with local makers, food trucks and more. Family and pet friendly and free to attend.
May 26
Dave Matthews Band is scheduled to perform in Tampa Bay as part of their 2026 North American Summer Tour, bringing their signature blend of rock, jazz, and improvisational jams to the MidFlorida Credit Union Amphitheatre. Known for their electric live performances and loyal fan base, the show promises an unforgettable night of music and summer vibes. Fans can expect a setlist packed with classics, crowd favorites, and a few surprises—making it a can’t-miss concert experience.
May 26-31
Based on the best-selling novel that inspired the iconic film, The Notebook tells the story of Allie and Noah, both from different worlds, who share a lifetime of love despite the forces that threaten to pull them apart. “Full of butterfly-inducing highs and beautiful songs” (Entertainment Weekly), The Notebook is a deeply moving portrait of the enduring power of love. Chris Jones of The Chicago Tribune says The Notebook is “absolutely gorgeous, not to be missed,” and The New York Daily News calls it “a love story for the ages.”
May 29
Laser Light Shows are taking over the Holloway Digital Dome Theatre, home to the Saunders Planetarium. Step inside America’s second-largest planetarium and experience vivid laser visuals, dynamic music, and dazzling special effects. Designed for all ages, MOSI’s Laser Light Shows have something for everyone. The performance pairs stunning visuals with your favorite Michael Jackson soundtracks. Inside the theater, you won’t just watch the show, you’ll feel like part of it.