by | April 28, 2026
What To Do This May in Florida
Surfing pups, wiener dog derbies, speedboat races, songwriter fests and more happening this May across Florida.
North
Isle of Eight Flags Shrimp Festival
Fernandina Beach
May 1–3
This three-day festival celebrates the city’s rich shrimping history with a shrimp boat decorating contest, a juried arts and crafts show and performers dressed as pirates storming the town. All weekend long, more than 300 vendors spread out across the historic downtown selling vintage wares, homemade goods and shrimply good eats. Look for booths marked with orange flags for fresh-off-the-boat shrimp that’s fried, boiled, put into tacos and more from strictly local sellers.
shrimpfestival.com
St. Augustine Food and Wine Festival
St. Augustine
May 6–9
The nation’s oldest city hosts a long weekend with one goal: taste, feast, repeat. The experience starts on Wednesday with a cocktail hour and The Saltworks Supper, where each dish is influenced by Southern cuisine and prepared with salt, from dry brining to cooking on hot salt. For the next couple of days, sample Spanish wines, nibble on curated plates made by local and regional culinary talent and attend soirees at the charming Ancient City Farmstead, where there’s more than 300 varieties of wines, beers and spirits to choose from.
staugustinefoodandwinefestival.com
Digital Graffiti
Alys Beach
May 15–16
At this Alys Beach art festival, pieces aren’t hung—they’re projected. Since its inception in 2008, Digital Graffiti has grown to feature more than 70 digital works from global artists, each carefully mapped onto the community’s iconic white buildings with the direction of Australian curator John Colette. Past installations include a live projection of a sand artist delicately creating intricate designs atop glass, an interactive display where participants change the images using a DJ board and an experience in which attendees try on the art by stepping into the light show and becoming a part of the display. Friday night offers a cuisine and cocktail experience for the 21 and over crowd, while the rest of the event welcomes art-appreciators of all ages.
digitalgraffiti.com
Pepsi Gulf Coast Jam
Panama City Beach
May 28–31
Swap your flipflops for boots and catch artists like Riley Green, Chris Stapleton and Post Malone bring the country to the coast for four days straight. Jim Beam provides custom cocktails like the Southern Sunset, which features pineapple whiskey mixed with orange juice and grenadine, then garnished with an orange slice and a cherry. Each night has a special theme for the crowd to match the killer sets, this year it’s: Neon Night, ‘Merica Night, Camo Night and Rhinestone Cowboy Night.
gulfcoastjam.com
Central
Tampa Riverfest
Tampa
May 1–2
Celebrate the 16th year of the Wiener Dog Derby, where hundreds of dachshunds race in different divisions such as senior dogs, puppies, disabled dogs using carts and more on a 50-foot track. Off the track, other competitions, such as best tail wag and best dog costume, will be open to all breeds. For two days there’s a guaranteed good bite with the Taste of Riverwalk on Friday offering restaurant samples from Lona Cocina and Bavaros Cocina, then on Saturday go to Tacofest where specialty tacos like crispy fish tacos with mango salsa and seasoned tofu tacos drizzled in peanut sauce, are offered for a limited time.
thetampariverfest.com
Hang 8 Dog Surfing Extravaganza
Daytona Beach
May 31
Hang loose and see pooches paddle out in this sun-soaked competition. Four-legged friends compete for the best wave and wipeout and for one category they’re joined by their owners for a human-dog tandem. Drop in on the Surfing Village filled with vendors who are stoked and stocked with pet apparel, toys and accessories like custom dog bowls to fit your dog’s height. Reminisce the surf and attend the after-pawty at the Hard Rock Hotel where the sound of live music and waves crashing fade into the evening.
daytonadogbeach.org
Thunder on Cocoa Beach
Cocoa Beach
May 14–17
This super boat grand prix offers more than just racing. Think: nightly street parties, meet-and-greets with racing teams and a food hall filled with local vendors like Coconuts on the Beach, a vibrant, coastal restaurant that serves . Hang out in the race village on Flounder Drive to see premiere powerboats, like top-tier Super Cats and elite Class 1’s, that can reach speeds up to 160 mph. Be on the beach all weekend long to watch over 40 teams navigate a nearly 7-mile course to be named the best in Super Stock and Class 1 categories.
thunderoncocoabeach.com
South
Key West Songwriters Festival
Key West
April 29–May 3
The Conch Republic reverberates with song this spring as music spills into the streets, sunset cruises and iconic haunts like Sloppy Joe’s during this annual Key West Festival. This five-day celebration pairs live performances with behind-the-scenes storytelling, giving regional and national talent a platform to showcase new music to fans and industry insiders. The groovy gathering has helped launch early careers for performers like Florida Georgia Line, Kacey Musgraves and Marren Morris. Intimate sets from artists take place on stages across the island, showcasing genres spanning country, pop, rock, and blues. Most shows are free, making it easy to wander from one set to the next and discover a new favorite along the way.
keywestsongwritersfestival.com
Florida Outdoor Expo
West Palm Beach
May 1–3
Test your aim with axe or arrow in target contests at this showcase for everything outdoors from adjustable fishing lures for bass to golf carts with built-in coolers. For three days, more than 200 vendors like Self Reliance Outfitters and 3rd Reef Line will be selling clothing, equipment and tools, sharing the stage with several competitions like People’s Choice BBQ Contest and DockDogs, where dogs jump off a long platform and compete for titles like furthest jump and highest vertical.
floridaoutdoorexpo.com
Miami Swim Week
Miami
May 27–31
Stop by exclusive pop-up activations from famous brands and rub elbows with celebrities for this swimwear fashion show in a city where a bikini is worn year-round. The Ritz Carlton South Beach hosts a mutli-brand event featuring designs from Diciembre Ventinueve, Page Beach and more. Don’t miss the sunset show at The Atlantic Hotel & Spa and other daily runways held atop pool decks showcasing more than 150 designs, which include emerging and international brands, spread across 20 venues in Miami.
miamiswimweek.com
