The best Miami events in May 2026 to look forward to

Bayskate is back, taking over the Historic Pan Am Hangar at Regatta Harbour in Coconut Grove for six weeks of roller skating, live DJs, cocktails, and outdoor lounges. You'll be gliding and grapevining around a 20,000-square-foot rink, with a gargantuan disco ball lighting up a place where some of America's first international flights began. This is, of course, a Miami-fied skating experience, with a cocktail program by Bayshore Club, with a rotating nighly soundtrack taht includes Latin tropibass, disco and, of course, Miami bass. The rink is open Thursdays through Sundays through June 14th, with daytime family sessions on weekends at lower admission prices. Groups can book rinkside table reservations, and season passes are available for unlimited access through the run. Skate rentals are available onsite, though you can bring your own Moxis or Impalas for extra style.

Every Wednesday night, Wynwood's PASTA opens its kitchen for a hands-on pasta-making class led by head chef Luis Jose. The restaurant — brought to life by acclaimed Peruvian chefs Juan Manuel Umbert and Janice Buraschi — blends traditional Italian technique with Peruvian influence, and the class reflects exactly that: you'll mix, knead and shape your own pasta before sitting down to eat what you made. A welcome cocktail, appetizer and dessert round out the evening.

If you grew up in a Cuban household in Miami, Álvarez Guedes was probably playing in the background. The comedian who became the Godfather of Latin Comedy through 30-plus albums of distinctly Cuban storytelling is getting the immersive treatment this spring. Debuting April 30 inside a custom-built venue at Tropical Park, Muerto de Risa is a three-hour cabaret-style production that moves guests through themed spaces — El Bar, El Cabaret, El Patio — as stand-up, live music and theatrical storytelling unfold around them. Less traditional theater, more like stepping into a night out at a classic Havana club. Learn more here. 

Two simultaneous exhibitions at the Lowe Art Museum on the University of Miami campus make up the most comprehensive presentation of Afro-Cuban art ever mounted. El Pasado Mio/My Own Past, organized by Harvard's Afro-Latin American Research Institute and expanded for its Miami run, brings together more than 81 works by 44 Cuban artists of African descent spanning two centuries, including nine paintings by Wifredo Lam and works by eleven female artists being exhibited together for the first time. The show restores artists who were deliberately erased from the Cuban art historical record, placing obscured figures like Pastor Argudin, Maria Ariza, and Tony Ximenez alongside better-known names like Agustin Cardenas and Maria Magdalena Campos Pons. The companion exhibition, Afrocubanismo: Highlights from the Ramón and Nercys Cernuda Collection, traces the cultural movement that emerged in the 1930s, when a generation of Cuban artists began centering the country's African roots at a moment when most of Cuban society had actively suppressed them. The tension in that moment is part of what makes the show complex: some of these artists are seen as co-opting a history that wasn't theirs; others as genuinely trying to re-imagine Cuba through its African roots and Afro-religious forms. On view through September 12. General admission is free.

The Balloon Museum's globe-trotting "Pop Air" exhibition has landed at Mana Wynwood, turning one of the neighborhood's most cavernous spaces into an entire immersive environment dedicated to inflatable art. The show has already toured Rome, Paris, New York, and LA, and the Wynwood footprint gives these installations more room than they've had anywhere. You're meant to wander, touch, and interact—through a geometric inflatable labyrinth, a suspended sphere installation that responds to movement, a room where balloons swirl in controlled tornadoes, and a massive LED-lit butterfly you can power yourself by pedaling. The standout is Hyperstudio's luminous projection-filled ecosystem of swings and shooting stars. Budget more time than you think you'll need; you'll want to stop and appreciate the scale of everything after filling your camera roll with selfies. 

After sell-out runs in Paris, Rome, and Milan, From the Heart to the Hands: Dolce&Gabbana arrives in Miami, opening February 6 at ICA Miami and running through June 14, 2026. The exhibition offers a rare look inside the creative universe of designers Domenico Dolce and Stefano Gabbana, tracing how their ideas move from inspiration to execution—all by hand. Curated by Florence Müller and produced by MARI, the show brings together more than 300 Alta Moda pieces, set within immersive installations and shown alongside works by contemporary artists, celebrating the artisanry, excess, and exuberance of Italian aesthetics. 

Gilded and crimson-draped Faena Theater is the ideal venue to experience OBSESSION, a new original production presented by Faena Live in collaboration with the Quixotic performance art collective. Nestled in Mid-Beach, the cabaret-style show blends live vocals, choreography and cinematic storytelling to take guests on a seductive 1.5-hour journey complete with lasers, projected visuals and plenty of theatrical haze. Helmed by emcee Sophia Bollman—whose credits include a stint on NBC's The Voice as part of Team Miley Cyrus and backup singing in Beyoncé's iconic Coachella performances—Faena Theater's 2026 headlining production also features the energetic stylings of Principal Violin and Musical Lead Kostia Lucky. Tickets start at $100 per person and include show admission only (food and beverages sold separately). Guests must be 18 or older, with a valid ID required upon arrival.

The World Cup is happening in Miami, and Wynwood is fielding its own culinary teams. The Wynwood International Food Festival runs June and July alongside the tournament, turning the neighborhood into a two-month global food trail with 20-plus restaurants each representing a different nation. The entry point is a physical passport — $25, available online or at partner locations — that gets stamped at each stop, with exclusive tasting items priced at $10 or $15 per restaurant. If you upgrade to a shot glass package, you get a welcome shot everywhere you go. The lineup spans Cuba, Japan, Korea, Lebanon, France, India, Italy, Mexico, and the United States, with familiar Wynwood spots like Cerveceria la Tropical, Ghee, Lira Beirut, and Fra Diavolo among the participants. Collect every stamp and you unlock exclusive prizes, not to mention bragging rights for saying you've basically eaten your way through Wynwood. 

If your Netflix algorithm includes Wild Wild Country and Wayward, the Museum of Sex Miami's new exhibition was made for you. Utopia: Three Centuries of Sexuality in American Cults and Communes, curated by filmmaker and publisher Jodi Wille, traces how over 20 American intentional communities — from the Shakers to the Rajneesh movement to the Source Family — used sexuality, spirituality, and art to build alternative visions of society across 300 years. More than 300 artworks, photographs, films, garments, and rare artifacts make up the two-story show, nationally recognized by Artforum and the Brooklyn Rail. On view through November.

Southeast Overtown/Park West Community Redevelopment Agency presents Sepia Vernacular, an exhibition that places Overtown’s past back into public view. Drawn from the City of Miami Planning Department archives, the show features more than 80 rare photographs from the 1920s–1950s, including selections from Max Waldman’s 1947 Color Town series, documenting daily life across the streets, businesses, families, and social spaces that seldom make it into Miami’s official histories. The exhibition will be taking place at the newly restored Lawson E. Thomas Building, which once served as the office of Miami-Dade County’s first Black judge and a central figure in the city’s civil rights movement. A newly commissioned mural by Anthony Mojo Reed II adds contemporary context which, together with the archival photo exhibition, frames Overtown as essential to understanding Miami, not peripheral to it.