Tampa sizzles with outdoor options and fun festivals all winter long

This Gulf Coast Florida city’s enticements are myriad: year-round sunshine, abundant outdoor offerings, and plenty of signature events
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Photo via Bigstock

Tampa has traditionally flown under the radar as one of the best-kept vacation secrets in the Southeast. But, as evidenced by its presence on “best of” lists everywhere these days (including TIME’s World’s Greatest Places 2023), the word is officially out about this Gulf Coast Florida city. Its enticements are myriad: year-round sunshine, abundant outdoor offerings, and signature events like the Florida Strawberry Festival and Gasparilla—the biggest and best pirate party in existence. While summers are predictably quite hot, visitors who come during winter and early spring are in for a treat: excellent weather (with minimal threat of hurricanes), a packed calendar of outdoor events (Yankees spring training, anyone?), and plenty of options for active exploration.

Tampa on Two Wheels

Biking is booming in Tampa, with 100 miles of designated bike lanes, a bike-share program, and a lot of helpful signage for exploring the city on two wheels. Get rolling with a rented ride: City Bike Tampa and Coast Bike Share, with rental stations along the Riverwalk, are both convenient choices for downtown excursions and ideal starting points for soaking up the booming waterfront scene. (Keep it slow: There’s a 5 mph speed limit.) The nearby Selmon Greenway is short but sweet, at just 1.6 miles, providing easy access to the Ybor City historic district.

Rental stations along the Tampa Riverwalk are ideal starting points for exploring the waterfront scene

Photo courtesy of Visit Tampa Bay

For a scenic adventure, hit the 10.5-mile Courtney Campbell Trail, a raised path alongside the Causeway connecting Tampa and St. Petersburg. Riding just above the water, you’ll have unbeatable views of the bay and boats below; you might even spot a dolphin or two. Flatwoods Park Trail, meanwhile, is a woodsy, seven-mile loop in the suburbs north of the University of South Florida. More serious cyclists can hit the Upper Tampa Bay Trail, an approximately eight-mile-long path built on an unused railroad corridor and known as one of the area’s best urban routes. It connects to the 55-mile Suncoast Trail leading north to Brooksville.

There’s something for mountain bikers, too: Alafia River State Park, with its radical elevation changes and steep drops (thanks to its location in a reclaimed phosphate mine), offers sweet MTB terrain. Its trails have earned an Epic designation from the International Mountain Bicycling Association and have something for all skill levels, from fun, flowy turns for beginners to hardcore drops and technical features for serious riders.

Alafia River State Park offers something for mountain bikers of every skill level

Photo courtesy of Visit Florida

Hey Batter, Batter

Beginning in February, Major League Baseball spring training kicks off and baseball fever spikes in Tampa. Yankees faithful flock to George M. Steinbrenner Field to watch the 27-time World Series Champs take the field at the state-of-the-art complex. But with four other teams—the Toronto Blue Jays, Philadelphia Phillies, Pittsburgh Pirates, and Detroit Tigers—within a 45-minute drive, baseball fans can easily see several clubs in action during their visit. “The weather is great, every team is tied for first place, and optimism can be found everywhere you look,” says Bryan Hoch, longtime Yankees beat reporter for MLB.com.

Yankees fans flock to George M. Steinbrenner Field to watch spring training

Photo courtesy of George M. Steinbrenner Field

Not only are spring training prices far more affordable than regular season tickets (some games start at just $10), but the atmosphere is also more relaxed since games don’t count. (The rocking chairs and checkerboards at Publix Field at Joker Marchant Stadium in Lakeland, where the Tigers play, perfectly capture the chill vibe.) And therein lies another perk of heading to the ballpark this time of year: a better shot of rubbing elbows with the pros. “The players are much more accessible during camp, as the stresses of the season haven’t yet set in,” Hoch says. “The venues are smaller and more intimate, making it a perfect opportunity to meet your favorite player for an autograph or selfie.”

Hoch’s top tip for scoring those: Do your homework on both the players and the venue: “Make sure to check websites and social media to see who’s in the lineup that day, then come prepared with a baseball, card, or other item that you are looking to have signed.”

Best-in-Class Beaches

Beaches in the Tampa area beckon with wide expanses of powdery white sand (which is actually made of quartz crystals, not shells) and warm water year-round. The best of the bunch are about a 45-minute drive west from town across the Pinellas Peninsula to the Gulf Coast. (If you’d prefer to stay in Tampa, get a taste of the ocean at Salt Shack on the Bay, a seafood dive that recently made The New York Times’ Best Restaurants in America list.)

Clearwater Beach, which consistently tops national “best beach” lists, is a stunner, with azure waves and powder-fine sand, plus Pier 60, a prime spot for fishing and sunset watching. When hunger strikes, choose from a cornucopia of nearby seafood shacks and watering holes. (Frenchy’s Rockaway Grill, located right on the beach, is a longtime locals’ favorite for its to-die-for She Crab soup and grouper sandwiches.) Traffic can get hairy on weekends, but once you’re in Clearwater, you can hop aboard the Jolley Trolley to hand off the driving: A $5 unlimited day pass stops at the beach, downtown Clearwater, and Sand Key, a pristine barrier island.

Clearwater Beach beckons with miles of powdery white sand

Photo via visitstpeteclearwater.com

Farther south, St. Pete Beach is another perennial favorite, with gorgeous swaths of coastline complemented by a classic Old Florida feel. To best soak up that retro vibe, head to the iconic Don CeSar, a sprawling, upscale resort that opened in 1928. The Pink Palace, as it’s also known, wrapped a multi-year renovation in 2022 and remains a stylish spot that draws both locals and visitors; a sunset cocktail is a fitting way to toast a great day at the beach.

Those searching for a more back-to-nature experience can choose from several local and state parks. A few worthy picks: Honeymoon Island State Park, with four-plus miles of beach and another three of trails through virgin slash pine forests; undeveloped Caladesi Island, accessible only via boat (you can catch a 20-minute ferry from Honeymoon); and Fort DeSoto Park, with five interconnected, undeveloped islands spanning more than 1,000 acres.

Kayaking is a popular way to explore Caladesi Island

Photo via visitstpeteclearwater.com

Gasparilla: Tampa’s Swashbuckling Shindig (January 20–March 2, 2024)

Bust out the Buccaneer gear, gather your best mateys, and get ready to grab some beads at the Gasparilla Pirate Festival. Named for legendary 18th-century pirate José Gaspar, who once terrorized the waters off west Florida, Gasparilla is an official season in Tampa. The first festival was held I 1904; nowadays, hundreds of thousands of visitors descend on Tampa to join the revelry, which spans massive parades (including the country’s third-largest), brunches and bar crawls, kid-friendly activities, and live music; there’s even a popular race with varying distances for ambitious athletic types (tagline: Aarrgghh you ready to run?).

Two must-see highlights, especially for first-timers: Ye Mystic Krewe of Gasparilla’s spectacular reenactment of the historic pirate invasion of the city—complete with a fully-rigged pirate ship and scores of bead-tossing buccaneers—followed by the Parade of Pirates, with more than 100 floats on the 4.5-mile route (things get a little rowdy toward the end; you’ve been warned). Hotels tend to book up months in advance, especially properties on the parade route or within easy walking distance (two newcomers to check out: The Roost, an extended-stay property, and JW Marriott Tampa Water Street). Several organizations, including Ye Mystic Krewe, offer tickets to watch the invasion over brunch, and you can also book a spot for viewing the parade.

Ye Mystic Krew of Gasparilla takes to the bay

Photo courtesy of Visit Florida

Families, meanwhile, shouldn’t miss Children’s Gasparilla: A full day tailored to pint-sized pirates, including an alcohol-free parade, air show, and fireworks. Gasparilla festivities also extend to other events, including a music fest, film fest, arts fest, and a night parade.

Paddling Paradise

Thanks to its location in Tampa Bay and proximity to three scenic rivers (Alafia, Hillsborough, and Little Manatee) Tampa is a place you can paddle for days. Tidal inlets, mangrove tunnels, and sparkling stretches of the Gulf of Mexico abound, so no matter what experience you’re craving—a day-long adventure exploring a secluded state park, or simply watching the sunset against a skyline—there’s a route that fits the bill. You can also count on some excellent wildlife viewing: sea turtles, rays, dolphins, alligators—even a manatee or shark.

For weekend visitors, a paddle through downtown offers an interesting way to explore the city. Several outfitters, including Tampa Riverwalk Rentals, have convenient kayak and SUP rentals along the Hillsborough River, which runs right through town. Take a leisurely paddle alongside Tampa’s 2.6-mile Riverwalk, which showcases the parks, museums, and dining spots of downtown’s ongoing renaissance. It’s equally impressive at night, with shimmering reflections from lighted bridges and glittering skyscrapers; some outfitters, including Urban Kai, offer full-moon events.

Paddlers who want to dip deeper into nature can head to Hillsborough River State Park, 20 minutes northeast of downtown. Bald cypress trees, strikingly clear water, and a shady route—as well as some Class II rapids, a rarity in Florida—make it a beloved spot among locals. Not surprisingly, weekends are busy, so arrive early; outfitter FloVibez has on-site rentals and guided tours. Post-paddle, you can even turn your outing into an overnight adventure: Timberline Glamping Company offers air-conditioned canvas tents, complete with mini fridges, for cushy camping at the park.

Timberline Glamping Company offers cushy camping options at Hillsborough River State Park

Photo courtesy of Timberline Glamping Company

With its calm bay waters, Tampa is also a great place to try kayak angling: a hybrid of fishing and paddling. “Kayak fishing provides the relaxation that paddling offers and the adrenaline of hooking a fish,” says Tatiana Cox Lopez, a certified kayak instructor and community outreach director for Tampa Bay Kayak Anglers, a nonprofit that promotes the activity and offers guided tours. “It’s a great sport for the mind and body, and it’s pretty easy to learn.”

With its calm bay waters, Tampa is a great place to try kayak angling

Photo courtesy of Tampa Bay Kayak Anglers

Fairs, Festivals, and More
What’s happening outside in winter and early spring

Florida State Fair, February 8–19, 2024
One of only a handful of wintertime state fairs, this 325-acre extravaganza attracts about half a million attendees over its 12 days. Of course, there are rides and games galore, plus interesting livestock exhibits (like a modern-day milking parlor). But the distinctly Floridian twist on traditional fair snacks is well worth the $15 fair admission alone: think fried Key lime pie, watermelon sweet tea, and Tampa Cuban funnel cake (a Cuban sandwich mashed between two funnel-cake slices). Don’t miss Cracker Country, a living museum that includes 13 original structures dating to 1870 and offers a fascinating peek into the daily lives of 19th-century Floridians.

Illustration by Rachel Winter

Florida Strawberry Festival, February 29–March 10, 2024
Move over, Florida oranges: Since the 1920s, the beloved strawberry has taken center stage during its namesake festival in Plant City. The sweet, juicy eats are certainly a draw (pro tip: do not miss the shortcake), but the music is a magnet, too: A-listers like Reba McEntire, Willie Nelson, Blake Shelton, and even Taylor Swift in her country era have graced the stage.

Illustration by Rachel Winter

Tampa Bay Beer Week, March 2–10, 2024
Toast Tampa’s exploding craft beer scene during this sudsy, eight-day affair, which celebrates the city’s impressive evolution into a bona fide Southeastern beer hub. On tap: brewing competitions, seminars, and, of course, tastings from the likes of Cigar City Brewing, which has been a major player in the local beer scene for nearly 15 years.

Illustration by Rachel Winter

Tampa Bay Wine and Food Festival, April 9–13, 2024
Wear forgiving clothing for this foodie extravaganza, which draws top restaurants and culinary talent from around the Tampa Bay area for multicourse dinners, cooking classes, and pop-up tastings. The VIP Chef Showdown is always a highlight, as chefs battle for top honors across categories like fried chicken, seafood, and tacos.

Illustration by Rachel Winter

International Cuban Sandwich Festival, May 26, 2024
Eat your fill of the beloved pork, ham, and cheese staple—Tampa’s signature sandwich—at this belt-stretching affair. Founded in 2012, the free festival features live music and a competition for the world’s largest Cuban sandwich (one previous winner measured 280 feet).

Illustration by Rachel Winter

This article appears in the Winter 2024 issue of Southbound.

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