From the active wildlife to the many cultural events, the cooler autumn air brings Pinellas County to life.


Fall in Clearwater, as with most of Florida, means the summer tourists have left with high tempts and the snowbirds have yet to arrive. An often-overlooked time to visit, it’s one of the best. From the active wildlife to the many art and food festivals, the Clearwater and St. Petersburg area comes alive as the humidity falls to a balmy and pleasant 60 percent in the afternoons.

Activities & Attractions

Dolphin Trail art sculpture

Walk With Dolphins

Fall and winter is a great great time to go explore the Clearwater Dolphins Trail, a public art pod of 120 playful dolphins designed by local artists in a variety of materials scattered all over Clearwater. Some must-see spots include Linger, decorated with lines of pine trees, at Honeymoon Island State Park, and Cleveland Street, where you can see Sun Dance and America the Beautiful. Or head to Tropicana Field to take a selfie with Skipper, sponsored by the Tampa Bay Rays and wearing a Rays jersey. Use this interactive map to chart your path.

Marvel at Monarchs during Peak Migration

It is an old Mexican belief that the orange monarch butterflies, who return to the country in time for Dia de Los Muertos, are the souls of loved ones returning for a visit. Thanks to the Gulf’s oil industry, in which the beautiful insects use the rigs as stopovers, Florida receives visits from them as well. In fact, September through November is their peak migration season, where thousands of butterflies stop into areas like Bayside Bridge Wetlands Conservatory and other wetlands around the city that are home to the monarchs’ favorite snack, milkweed.

Catch the King

There are actually two peak seasons for kingfish: spring and fall. But the latter season is when you’ll find true behemoth versions of the species (which are actually a type of mackerel) roaming these waters. That’s because it’s the season when they migrate back down south for the winter, after they’ve spent the summer getting fat off squid, anchovies, and jack. By the time they make it back to the Clearwater area, these fish weigh an average 20 pounds. The best way to find kingfish is by taking a charter like Scales and Tails off the coast and casting your line into the deeper waters of the Gulf.

Stroll Through Festive Flora

From late-November through December, the Florida Botanical Gardens turn into a winter wonderland thanks to the annual Holiday Lights in the Garden. Located just nine miles south of Clearwater and 10 miles north of St. Pete in Pinewood Cultural Park, the 30 acres of cultivated gardens are adorned in more than one million LED lights, as well as festive holiday displays of snowmen and Santas. Local musicians dot the gardens, serenading guests as they wander the lit pathways while sipping on hot chocolate and munching on sweet snacks from local vendors.

Festivals & Events

GeckoFest, 8/31

Gulfport, located just outside of St. Pete, is known as the “quirkiest town in America.” In fact, the town celebrates that unique distinction every Labor Day with this street fair showcasing the artists and performers that make Gulfport such an interesting town.

SHINE Mural Festival

SHINE St. Pete Mural Festival 10/18–26

While St. Petersburg is already known as a destination for street artists, each year, the city looks to add new pieces to its already large mural collection thanks to this annual 10-day event. Expect 16 local and international artists making their mark on the city while crowds gather to watch the mesmerizing process.

Clearwater Jazz Holiday, 10/17–20

While the lineup is still being finalized for 2019, Clearwater’s premier four-day jazz fest held in Coachman Park has pulled in the likes of past performers such as Gladys Knight, Buddy Guy, and the Count Basie Orchestra.

Shopapalooza Festival, 11/30–12/1

To kick off the holiday shopping season right, start at this admission-free street fair, featuring vendor booths by more than 200 local small businesses.

Outback Bowl Beach Day, 12/30

Every New Year’s Day, two college football teams face off in Tampa Bay, but the real event takes place the day before. The teams, joined by their cheerleaders, mascots, and the marching bands compete in a series of competitions in a Drumline-style battle of the bands, tug-of-war, and a pie-eating contest.

Where to Stay Opal Sands ResortSandpearl Resort | Treasure Island Beach Resort