The natural world in and around Sarasota opens up during these summer months in a way most people don’t get to see. From a once-a-year blooming cactus to fresh fruit and game fish, the world of Sarasota becomes a play land of natural beauty, which is mirrored in the city’s summertime dedication to the arts.

Activities & Attractions

Catch some Prime Fishing

One of Sarasota’s most popular fishing stops is the New Pass Bascule Bridge that connects Longboat Key to Lido Beach. While anglers converge on the bridge all year long to try to hook snook, blue fish, and flounder, the months of May and June are tarpon season – Florida’s favorite game fish – on the Gulf, with several fishermen making record catches around it. Stop by New Pass Grill & Bait Shop to stock up on equipment and bait and to pack the cooler with sandwiches and beer. Or, for an even better chance of catching, charter a boat like Wrightstuff Charters to go offshore and see for yourself why these aerial fighters are considered some of the toughest to catch.

Top Things to Do in Sarasota in May & June

Experience Warhol in Nature

When people think of Andy Warhol, they usually imagine technicolor prints of soup cans and starlets, but a vast portion of the iconic pop artist’s body of work featured natural elements. In recognition of that, Marie Selby Botanical Gardens and Museum is hosting Flowers in the Factory, a collection of Warhol work that focuses on flowers and other natural elements, until the end of June. In conjunction with the exhibit, the museum also is featuring Warhol Nights which bring in local entertainment, like the Sarasota Orchestra in June, while guests take in the exhibit and meander the gardens at sunset.

Find the Freshest Fruits

The Sarasota Farmers Market has grown to be one of the largest in the state, with over 80 vendors lining Lemon Avenue in downtown Sarasota. During these peak summer months, the best time to hit the market is between 7 a.m. (when it opens) and 10 a.m. Coming in early allows you to beat both the heat and the crowds and the vendors will still be in full supply. Not to mention, May and June are the peak season for cantaloupes, watermelons, and fava beans, though you can also find home made jams, fresh honey, and baked goods among the downtown stalls.

See a Rare Blooming Flower

Once a year, usually in late May or early June, Marie Selby Botanical Gardens hosts a special street watch party for the selenicereus flower (a.k.a. Queen of the Night), actually a transplant from Arizona’s Sonoran Desert. So what’s so special about this flower – a type of blooming cactus, actually – and why do people make the pilgrimage to see it? Because, on a single evening each year, as twilight moves to night, spectacular blossoms open up all along the length of the plant’s sinister-looking vines – but only for a few brief hours. As dawn creeps in on the horizon, the petals close up and fall off. Definitely bring your camera for this one.

Catch a Show

Sarasota is home to a host of theaters, from big art halls like the Van Wezel and Asolo Repertory to small black-box venues, like the Urbanite Theatre. Starting in May until the end of summer, nine of them come together to create the Sarasota Summer Stage, a citywide deal on tickets. For comedy, check out McCurdy’s with free shows on Sundays, Wednesdays, and Thursdays. If you’re looking for something more serious, The Players Center offers 10 perfect off on their off-Broadway productions.

Festivals & Events

Sarasota Craft Fair, 5/7 & 5/8

Sarasota is known for its tightly woven arts and crafts scene, which hosts four major events a year including this special weekend in May. More than 100 crafters from across the country converge in downtown, and sell everything from jewelry and pottery to photography and paintings to clothing and handmade soap. There’s also a “green market,” where local growers offer up Florida-grown orchids, sunflowers, and birds of paradise.

Outdoor Pops Field of Dreams, 5/11 & 5/12

For two nights, the Sarasota Symphony Orchestra takes over Ed Smith Stadium for the Outdoor Pops. Guests munch on popcorn and ball park franks while the orchestra plays favorites from La La Land, Grease, and other Disney films. At the end of each night, the stadium lets off fireworks that rival any Fourth of July display.

St. Armands Seafood and Music Festival, 5/26 & 5/27

Each year, Sarasota’s top seafood restaurants come together at St Armands Circle to celebrate two days of culinary creativity. Tickets include samples of food made on-site and live music provided by local bands. For $130 a ticket, the VIP tent includes an unobstructed view of the performances as well as a raw bar, full bar, and table service in the shade.

World Oceans Day Film Festival, 5/31

The Mote Marine Laboratory and Aquarium hosts a touring conservation based film festival every summer, which features the best nature and nautical documentaries of the year. This year includes Paradigm Lost, a story about how watersports connect with the ocean life of Hawaii, and Vamizi, a documentary about the coral reefs off Mozambique, with beautifully shot sequences that rival that of Blue Planet.

Top Things to Do in Sarasota in May & June

Sarasota Music Festival, 6/3–24

During this three-week event, Sarasota invites students of classical music to learn under some of the most highly respected and sought-after musicians from around the world. Each Friday, when classes are over, the student and teachers collaborate to put on small chamber shows in the evenings that are followed up by major symphonies each Saturday.

Where to Stay The Resort at Longboat Key Club | Lido Beach ResortZota Beach Resort