From the Panhandle to Tampa Bay, discover the best ways to celebrate seafood, music, art, and more.

By Tracey Minkin and Susan Hall Mahon
March 08, 2019
Clearwater Jazz Holiday
courtesy of P. Widoff

Festivals — whether they be food, wine, music, or art — are perfect ways to build a bit of learning and considerable dose of fun into a few days. And when those festivals pop up along the white sands and turquoise waters of Florida’s Gulf Coast, the whole thing just gets better and better. Get a dose of sun, sand, and play at these ten great festivals.

SarasotaMOD Weekend, Sarasota
Discover one of the most stunning collections of midcentury modern architecture (on some of the country’s most beautiful beaches) in this three-day festival in November that includes exclusive house and trolley tours, lectures, film screenings, an art exhibition, evening social events, and whole lot of ogling.

UNwineD, Panama City Beach
This two-day celebration of wine from around the world, craft beer, and crafted spirits and cocktails takes place in the fun, sun-loving destination of Panama City Beach on the white-sand Florida Panhandle. A Friday night kick-off party leads to a Grand Afternoon Tasting that includes art and boutique displays, followed by an outdoor concert in a new park just steps from the beach.

Paddle at the Porch, Destin
Grab a board and try your hand at stand-up paddleboarding on the crystal-clear Gulf waters. This SUP event features 1-, 3-, and 6-mile race options, with a cash prize awarded to winners. Bonus: The contest takes place on the beach directly in front of Destin’s beloved Back Porch restaurant, where you can chill post-race with a plate of ice-cold oysters and beer.

30A Songwriters Festival, South Walton
Each January, Florida’s Highway 30A transforms into a music-lover’s Eden when hundreds of artists come to play intimate venues steps from the Gulf’s flour-soft sand. Emmylou Harris, Jason Isbell, Brandi Carlile, and Rosanne Cash are just a handful of the incredible musicians who have played sets at small, low-key venues like Old Florida Fish House in Seagrove Beach, Bud & Alley’s in Seaside, and the Rosemary Beach Town Hall.

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Great Gulfcoast Arts Festival, Pensacola
Historic Seville Square swells with more than 200 juried entrants in this three-day November festival that showcases painters, potters, sculptors, graphic artists, jewelers, and other craftspeople. The action carries on with live music, demonstrations of traditional arts, crafts, and trades, and an inspiring student art show featuring more than 2,000 works by local public school students.

30A Wine Festival, Alys Beach
While the centerpiece of this five-day February event is a Grand Tasting along this stunning beach community’s picturesque South Charles Street and features high-end wines and small plates from outstanding local chefs, the entire weekend fills with delicious options. Exclusive wine dinners, seminars, a bourbon and BBQ night, and a rousing day of rosé and competitive croquet round out the fun.

Destin Seafood Festival, Destin
“The World’s Luckiest Fishing Village” puts its fresh-from-the-Gulf wares on display each October along the Destin Harbor Boardwalk. Shrimp, lobster, grouper, and crawfish are just the beginning of the local catch served up by Destin’s most well-known seafood restaurants. Admission is free, and there are activities for kids and four stages featuring live entertainment.

Pepsi Gulf Coast Jam, Panama City Beach
Panama City Beach closes out summer with a bang at this three-day country music festival that’s held every Labor Day Weekend along the sparkling waters of Florida’s Emerald Coast. Carrie Underwood, Martina McBride, Keith Urban, Toby Keith, Brad Paisley, and more blockbuster artists have headlined.

Digital Graffiti Festival, Alys Beach
The iconic white-walled buildings of dreamy Alys Beach, along Florida’s 30A, become a spectacle of swirling lights and colors every May at this projection art festival, the first of its kind in the world. Digital artists, photographers, filmmakers, and designers submit their work for consideration, and accepted entries have the chance to win in three categories: best in show, curator’s choice, and special recognition.

Clearwater Jazz Holiday, Clearwater
Clearwater, home of the Best Beach in America (two years running!), plays host to this four-day jazz, blues, folk, and rock festival — with world-class acts like Earth Wind & Fire and The Avett Brothers — each October. The al fresco celebration takes place at Coachman Park, a swath of green grass surrounded by swaying palm trees and fronted by the turquoise waters of Clearwater Harbor.