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What to Do in Tampa, Florida

I live 15 minutes from Tampa, Fla., but I hardly ever visited the Gulf Coast city when I moved to nearby St. Petersburg in 2019. My friends in St. Pete dismissed the place as a sprawling, sun-baked collection of strip malls, and the traffic on the Gandy and Howard Frankland bridges connecting the two cities was an incentive to stay on “our” side of the bay. Then the pandemic came and with it more time in the area and a lot less traffic.

My initial forays to “their” side of the bay were aimed at finding things my new hometown lacked, beginning with tennis, Turkish food and tamales. I discovered Racquet Heads, a wonderful little tennis shop hidden underneath a highway overpass. Then I became addicted to the kebabs and lahmacun (Turkish pizza) at Istanbul Mediterranean Grill & Restaurant near the Busch Gardens theme park, and the irresistible tamales at Lolis Mexican Cravings, an excellent fast-food Mexican restaurant with five locations in Tampa.

I wasn’t the only one checking out Tampa. In 2020, Tom Brady came to town, and it hasn’t just been the area’s excellent sports teams that have been on a winning streak of late. The flood of Northerners in search of sandals-and-shorts winters accelerated during the pandemic. Zillow, the real estate website, recently forecast that Tampa will be the hottest housing market in the country this year, and Forbes named Tampa the number one emerging tech city in the nation last summer. The city’s revitalized downtown will get another boost with the eco-friendly Water Street Tampa project, which will bring 3,500 new downtown condos, along with retail and hotel developments, including the soon-to-open EDITION, a striking luxury hotel, steps from the Hillsborough River.

Long overshadowed by Miami, Orlando and Key West, Tampa is emerging as a cool place to live. But is it really a place to spend your vacation?

From a tourism perspective, this city of 400,000, tucked into a metro area of about three million, remains a bit of a secret, despite its recent growth. Many visitors still fly into the Tampa’s award-winning airport and head straight to the beaches in St. Petersburg and Clearwater. But as I’ve found in my recent travels, they may be missing something.

William Drysdale was a peripatetic writer who wrote more than 50 “travel letters” from Florida in the late 19th century for The New York Times. On his first trip to Tampa Bay in 1884, the year the railroad magnate Henry Plant introduced rail service to Tampa, Drysdale extended a one-night stay into a fortnight. “After visiting nearly all the warm countries frequented by Americans, Cuba, Mexico, Bermuda, Yucatan, Texas, Louisiana, and many of the smaller West India islands,” he wrote, “I like the West Coast of Florida best of all.”

Florida Historical Quarterly credits Drysdale’s Florida dispatches with helping “create a winter tourism bond between New York and the sunshine state which has remained firmly in place for more than 100 years.”

Before Plant opened the Tampa Bay Hotel — his lavish, “fireproof,” 511-room, Moorish-style palace — in 1891, Drysdale was given a preview and wrote a gushing dispatch, claiming “its domes and spires … its 150 acres of groves, its 2,000 electric lights, its brick walls and steel beams” made it, along with Henry Flagler’s Ponce de Leon hotel in St. Augustine, one of “two great hotel wonders of the world.”

The Tampa Bay Hotel put the city on the map, but it fell on hard times within a decade of Plant’s death in 1899. According to the book “Tampa’s People with a Purpose,” the once-grand old dame became “a red elephant that was at times occupied by vagrants who burned some of (Plant’s expensive) furniture to stay warm.” It closed its doors during the Great Depression and is now part of the University of Tampa.

The former hotel remains Tampa’s most Instagrammable landmark, though many visitors leave without visiting the excellent Henry B. Plant Museum inside, which gives a colorful account of the hotel’s early days. (If you plan to visit other attractions along the city’s Riverwalk, like the outstanding Tampa Bay History Center, the Glazer Children’s Museum, the Florida Aquarium or others, consider buying the new Riverwalk attraction pass.)

To get a different perspective on the hotel’s iconic domes and Tampa’s skyline, you can rent an electric boat from eBoats Tampa and take a spin on the Hillsborough River, making pit stops at watering holes like Rick’s on the River and gliding by the Davis Island mansion formerly owned by Derek Jeter and rented by Tom Brady before it sold last year for $22.5 million.

I got the electric boat recommendation and many others from Steven Hoffstetter, a fifth-generation Floridian and a Tampa native. “We hate St. Pete and they hate us,” he joked. “Seriously, I prefer Tampa.”

Mr. Hoffstetter stressed that visitors must spend time on the water to understand the culture. He recommends taking a charter excursion via Tampa Bay Fun Boat to boozy Beer Can Island (a.k.a. Pine Key) which has a bar (“open when the weather is good, the water is calm and the hangover is manageable”), but no permanent inhabitants.

To understand Tampa’s watery geography, you must learn the legend of José Gaspar, a Spanish pirate who reputedly stole a ship in 1783 and sailed to the Gulf of Mexico, where he and his crew raided with abandon until 1821, when their ship, the Gasparilla, was sunk by the U.S.S. Enterprise. Gaspar, the legend goes, wrapped himself in the ship’s anchor chain and threw himself out to sea, proclaiming, “Gasparilla dies by his own hand and not his enemy’s!” Gaspar was largely forgotten until 1904, when Louise Frances Dodge, a society editor at the Tampa Tribune, cooked up the idea for a pirate-themed parade based on his legend.

If you happen to be here in late January, you can party with thousands of revelers, many dressed in pirate garb, who turn out for the Gasparilla parade along Bayshore Boulevard, which is turned into a “wet zone” where open containers of alcohol are permitted. Hundreds of pirates perform a ceremonial invasion, in which the mayor hands over the keys to the city. But what many visitors don’t realize is that the Gasparilla revelry continues after the initial invasion with a season worth of activities, including music and arts festivals and the Sant’Yago Knight Parade. The debaucherous celebrations are only-in-Tampa spectacles worth anchoring a trip around.

Another singular Tampa experience is taking a boat to the Sunday morning Thai market at Wat Mongkolratanaram, a stunning Buddhist temple with boat docks on the Palm River. Come early to beat the crowds who flock to this popular market for cheap, homemade Thai food and beautiful orchids and other flowers.

In a modern city, the natural tendency is to search for something old. The best place to experience Old Tampa is Ybor City, a neighborhood that was once famous for producing quality cigars. Its main drag, East 7th Avenue, is the city’s pulsating nightlife hub. Visitors rarely stray off 7th Avenue, but several treasures are hidden around the neighborhood. Start with the Ybor City Museum, where you’ll learn the fascinating story of the neighborhood’s founder, Vincent Martinez Ybor, a Spanish businessman in Havana who ran afoul of Spanish authorities in 1868 for supporting Cuban independence.

Facing the prospect of death by hanging, he escaped to Key West, which lacked adequate transportation links for his cigar business. He built Ybor City in 1886 as a planned industrial community at a time when Tampa had just 2,735 residents. (The area’s earliest inhabitants were the Native American Calusa, and the word Tampa comes from the Calusa word “Tanpa” which meant sticks of fire, a reference to the area’s legendary lightning strikes.)

Tampa came to be called “Cigar City” as legions of Cuban, Spanish, Sicilian and Romanian Jewish immigrants streamed into Ybor to toil in its cigar factories. The industry drifted into a gradual decline starting in the 1920s, but you can tour the J.C. Newman Cigar Company, the city’s last cigar factory, and enjoy stogies at many neighborhood establishments.

Around the corner from the museum, the recently opened Tampa Baseball Museum chronicles the region’s baseball history in the childhood home of Al López, Tampa’s first pro ballplayer. Tampa has been the spring training home to seven teams, dating back to 1913 when the Chicago Cubs trained there. Meanwhile, the legendary Yankees teams of the 1920s, ’30s and ’50s trained in St. Pete and have been in Tampa since 1996. Teams were lured to the region to promote tourism, and spring training games, which run this season until April 6, are still a big draw.

A good spot for lunch is Al’s Finger Licking Good Bar-B-Que, where you can sit at the counter and inhale the smoky goodness of pulled pork and ribs, or dine outside, where you’ll hear the neighborhood’s clucking chickens, which have their own fan club, the Ybor Chickens Society. Another nearby hidden treasure is Barriehaus Beer Company, which has excellent German and Czech-style lagers and a kid- and dog-friendly beer garden. If you have a sweet tooth, cap your Ybor City tour off at the century-old La Segunda Central Bakery, which is famous for its three-foot-long loaves of Cuban bread, Cuban sandwiches and irresistibly buttery treats, but has an off-the-beaten-track location just north of Ybor City’s historic district.

The best way to navigate Tampa’s sprawl of less-heralded neighborhoods is to eat and drink your way around town. Inflation is a buzz kill, but luckily the immigrants who run the West Tampa Sandwich Shop and the Saigon Deli haven’t received the raise-your-prices memo. The sandwich shop is a hangout for Cuban immigrants, and their $4.50 Cuban sandwich is a bargain, as is the $4 grilled pork banh mi at Saigon Deli (3858 West Waters Avenue), a wondrous, yet humble, Vietnamese eatery hidden away in a strip mall alongside a Vietnamese market and cultural center.

While we’re talking four buck treats in Tampa, put timeless Bo’s Ice Cream (7101 North Florida Avenue), a Seminole Heights institution run by four generations of the Bosanko family since 1954, on your dessert itinerary. Bo’s has excellent custard, and their ($4) “small” hot fudge sundae with whipped cream and nuts is big and appropriately sinful.

The Seminole Heights, Tampa Heights and Hyde Park neighborhoods are silly with worthwhile hidden locals’ joints you ought to try. Call ahead to get a password to enter Ciro’s Tampa, a beautifully appointed speakeasy-style cocktail bar in an old hotel-turned-condominium building. On a residential street in Tampa Heights, you’ll find perhaps the city’s best pizza and wings at Lee’s Grocery, a pizzeria and bottle shop with a dog-friendly patio. And near the airport, the humble, eight-table One Family Korean restaurant is hidden between a Korean supermarket and a Korean cultural center at the end of a strip mall where you can get awesome bulgogi (thin, marinated slices of beef or pork) and delicious Korean barbecued short ribs as a reward for finding the place.

Tampa can seem like a sprawling mess when you’re driving around busy six-lane roads in search of hidden $4 sandwich shops, so make time to decompress in green spaces like Lettuce Lake Park, where you can rent a canoe or kayak ($25 for up to four hours, no reservations), and Hillsborough River State Park ($6 entry per car), where you can hike in an Old Florida jungle on an easy 2.5-mile loop via the Baynard and River Rapids trails.

As I made one rewarding discovery after another while cruising Tampa’s broad avenues, I concluded that the city’s hidden charms are impossible to catalog in a systematic way. Make your own tracks and cover them well. I prefer to leave some nearby terrain unexplored so I never feel like there’s nothing left to discover in my own backyard. But for two weeks, I commuted across the Bay, living the life of a Tampeño, all the while feeling a bit like a spy, perhaps even a traitor. I learned that Tampa isn’t the bland and forgettable city I was told it was, and I enjoyed every minute of my subversive travels to the other side.

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