SOUTH

Little Palm Island Sandbar Sessions

Little Palm Island
May–August

Toes in the sand, a drink in your hand and the sun setting behind your favorite band? Sounds like a summer dream—better known as Little Palm Island’s Sandbar Sessions. Lit by tiki torches and moonlight, these private-island concerts appeal to passionate music lovers. The up-close-and-personal musical immersion features artists like Stephen Marley, Indigo Girls and Anders Osborne, who all perform an ultra-intimate concert on Little Palm Island’s iconic sandbar and mingle with guests before and after the show. Sandbar Sessions unfold with an element of surprise, as musicians are revealed only a month or so before their performance date. Staying at the resort guarantees your place at this seaside serenade, but there are a limited number of tickets for “off-island” fans, so be sure to check the website frequently. littlepalmisland.com

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American Black Film Festival

Miami Beach
June 14-18

Now in its 27th year, this empowering event celebrates Black excellence in the entertainment industry. Catch screenings of acclaimed indie films, sit in on celebrity panels and maybe even spot this year’s festival ambassador, Emmy-winning writer, actor and producer, Lena Waithe. abff.com/miami

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VFW Fishing Tournament

Key West
June 16-18

The heftiest haul reigns at this family-friendly fishing tournament in the Keys. Anglers with the biggest dolphinfish, wahoo, snapper, grouper and tuna will take home thousands of dollars in cash prizes. vfwpost3911.org

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Delray Concours D’Elegance

Delray Beach
June 16-17

Auto aficionados from all over gather in Delray Beach to marvel at Maseratis, Mercedes, motorcycles and more. Falling near Father’s Day, it’s the perfect present for the gearhead guys in your life. delrayconcours.com

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Key Lime Festival

Key West
June 30–July 4

Florida’s beloved citrus takes the limelight at this annual festival featuring a rum-tasting experience and a pie drop, where participants must drop their pies from the top of the lighthouse without damaging them. keylimefestival.com

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Miami Swim Week

Miami Beach
July 4-10

From halter tops and high-waisted bottoms to string bikinis and bandeaux, see what’s in style for swimsuit season this year at runway shows across the Magic City. You never know what might make a comeback. miamiswimweek.net

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LobsterFest

Key West
Aug. 10-13

Feast on so many lobsters that you lose count at this Key West kickoff. Whether you like a traditional down-home boil or an upscale crustacean culinary experience, discover countless ways to enjoy your claws. keywestlobsterfest.com

CENTRAL

St. Pete Pride Festival

St. Petersburg
June 1-30

Wave your flag high and dance in the multicolored confetti rain at the largest Pride festival in Florida. To commemorate the 21st annual celebration, the Sunshine City is partying all month long with free LGBTQ+ events leading up to its iconic street parade, including a Friday night concert with famous queer musicians, a street carnival with hundreds of vendors and even a chance to belt out your favorite ally anthem at Queer-E-Okee. Black and Brown members of the LGBTQ+ community are at the center of the Shades of Pride celebration, where their voices and art will tell the history of Juneteenth. Later, lace up your sneakers and log some steps from Vinoy Park to Albert Whitted Park in support of our transgender and gender-nonconforming friends at the TransMarch. The festivities culminate in a waterfront parade of positivity, empowerment and, most importantly, pride on June 24 up Bayshore Drive. stpetepride.org

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Florida Wiener Dog Derby

Tampa
May 6

Speedy things come in small packages. Watch four legs, fur and floppy ears fly at this comical competition. Don’t have a dachshund? Other bite-size breeds can also feel the wind in their ears in the Wiener Wanna-Be division. floridawienerdog-derby.com

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Guy Harvey Weekend 

Tampa
May 26-27

Throw on your favorite Guy Harvey shirt, and meet the man behind the brush at Busch Gardens. Talk all things conservation, art, diving and marine life over mimosas at brunch with Harvey or swing
by for a quick snapshot with the scientist before sneaking one last ride on Sheikra after sunset. buschgardens.com

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Silver Spurs Rodeo

Kissimmee
June 2-3

Brawns and bravery are on full display at the largest rodeo east of the Mississippi. From classic bull riding to steer wrestling and tie-down roping, watch cowboys and cowgirls compete for the purse—and some serious Southern street cred. silverspursrodeo.com

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WEC Summer Series

Ocala
June 13-Aug. 13

Settle into the stands at the new World Equestrian Center for an evening of equine adrenaline. Professional riders come from all over the world to compete in this hunter/jumper series that runs throughout the summer. worldequestriancenter.com

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Old Salt Ladies Fishing Tournament

Madeira Beach
June 22 & 24

Head out for a different kind of girl’s weekend when you register for this massive all-female fishing tournament. Lady anglers race to reel in the biggest redfish, grouper, snook and more while raising money for the Celma Mastry Ovarian Cancer Foundation. Plus, a $10,500 purse doesn’t hurt. oldsaltfishing.org

NORTH

Flamboyance! A Topiary Menagerie 

Jacksonville
April 1–June 25

Fifty flamingos have descended on the Cummer Museum of Art & Gardens, nesting on the 2.5-acre grounds adorned with live oak trees, blooming azaleas and Italian statues along the St. Johns riverbank. Each bright pink begonia-lined bird brings a sense of whimsy and wonder to the traditional 100-year-old gardens. You’ll find these floral friends sprinkled throughout the Olmsted, English and Italian gardens, giving the otherwise formal landscape a playful flair. Snack on house-made crab cakes or flatbread du jour from the Cummer Cafe while strolling through the horticultural exhibition—or, better yet, bring a blanket and reserve a spot for an exclusive Friday night picnic. This flowery flock will only be in bloom until June 25, so be sure to buy tickets before they fly home to the Franklin Park Conservatory in Ohio. cummermuseum.org

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St. Augustine Food + Wine Festival

St. Augustine
May 3–7

Stroll along some of the oldest roads in America while sipping a syrah at one of Florida’s best food and wine festivals. Both local and celebrity talents will pull together themed dinners, cooking demos and wine tastings to impress your palate. staugustinefoodandwinefestival.com

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Isle of Eight Flags Shrimp Festival

Fernandina Beach
May 5–7

This seafood soiree is more than just an excuse to feast on fried shrimp, it’s also a nod to the area’s unique background of being a territory controlled by eight different flags over the last five centuries. shrimpfestival.com

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As If! The ’90s Fest

St. Augustine
May 20

Crimp your hair, and dig out your combat boots because this one’s for you, ’90s babies. Vanilla Ice and the Spin Doctors headline this dreamy night of nostalgia at Francis Field. asifthe90sfest.com

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Tupelo Honey Festival

Wewahitchka
May 20

See what all the buzz is about at Wewahitchka’s famous annual tupelo honey celebration, where visitors can taste test sweet samples from beekeepers’ booths around Lake Alice. tupelohoneyfestival.com 

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Gulf Coast Jam

Panama City Beach
June 1-4

Grab your whiskey glasses, and trade your boots for barefeet because this is four days of country music carousing by the coast with headliners Morgan Wallen, Miranda Lambert, Hardy and Kane Brown.
gulfcoastjam.com

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Greater Jacksonville Kingfish Tournament

Jacksonville
July 17-22

With divisions for junior anglers, dock fishing and lady anglers, everyone has an opportunity to hook a big one at this tournament that benefits marine research and preservation. kingfishtournament.com