Three Perfect Days: A Trip to Tampa

It’s my first morning back in Tampa, where I grew up, and I’m awakened by the faint sound of roosters. I’m not staying on a farm but at Hotel Haya, a boutique hotel in historic Ybor City. Street-strolling hens are ubiquitous in this district. The area was born in 1885 as a workers’ community for cigar rollers, with a population that drew heavily from Cuba and Sicily.

Ybor’s main route, 7th Avenue (La Séptima), is something of a Floridian Bourbon Street. It's filled with tattoo parlors and nightclubs, but many businesses have re-embraced the neighborhood’s roots. Hotel Haya, for instance, incorporates two historic structures. It is named after local power broker and cigar pioneer Ignacio Haya.

In need of some caffeine to start the day, I make my way down to the lobby’s Café Quiquiriqui—which I learn is how roosters say cock-a-doodle-do en español.

After a tres leches latte—made with evaporated, condensed, and whole milk—I stop into the 108-year-old La Segunda Bakery a few blocks away. I order a guava turnover and a crusty loaf of Cuban bread. The latter gets its signature crease from a palm frond pressed into the dough.

I leave a Hansel-and-Gretel breadcrumb trail that will please the roosters as I wander over to José Martí Park, which honors the “Apostle of Cuban Independence.” A couple from Havana bought the land and deeded it to Cuba’s government in 1956. Even after the revolution, the 0.14-acre park is still technically considered Cuban soil.

Along 7th Avenue, I stop in at a pair of cigar shops, Tabanero and Nicahabana, where cigars are still hand-rolled on-site, the old-fashioned way. If you’re lucky, you might catch artisans hunched over their wooden desks, as they fastidiously select each tobacco leaf, cutting and rolling them with almost monk-like precision. At Tabanero, where the air hangs thick with the earthy incense of tobacco, I buy a few maduros, which means “matured” or “ripe” in Spanish, as gifts for friends. They have a sweeter, smoother taste thanks to their fermented wrappers, but in truth I just choose this style because they’re what inspired my favorite local craft beer, Cigar City Brewing’s Maduro Brown Ale.

Lunch is at Columbia Restaurant, where the ornate dining room often hosts flamenco shows. I’m drawn, however, to the understated bar. Squint and you can picture cigar rollers eating Cuban sandwiches here back when the place opened in 1905. There is, in fact, an ongoing debate about whether the Cubano got its start in Tampa or Miami. Those who support the Tampa hypothesis note that each ingredient represents one of Ybor’s founding immigrant communities: ham (Spaniards), roast pork (Cubans), Swiss cheese, pickles (Germans) and, only in Tampa, Genoa salami (Italians). I’ve always thought the city should replace its flag with a giant Cuban sandwich banner.

After lunch, I stop to take pictures of the “Viva Ybor” mural. It features Spanish entrepreneur and neighborhood founder Vicente Martinez Ybor. Next door, at the quirky gallery Dysfunctional Grace Art Co., I peruse protection charms made from alligator skulls and dried chicken feet (don’t tell the cluckers outside). I then stop into The Blind Tiger Coffee Roasters, which also sells items from local apparel company Black & Denim. I can’t leave without a “Support Tampa Hospitality Workers” T-shirt. I appreciate its message, but if I’m being honest, I love the design even more: an anthropomorphic Cuban sandwich carrying another Cuban sandwich.

From here, I take the free canary-yellow TECO Line Streetcar downtown to Water Street. Tampa Bay Lightning owner Jeff Vinik and Bill Gates have invested $3 billion to develop luxury hotels, offices, shops, and residences in the area. It’s still a jungle of cranes and scaffolding, but the stretch adjacent to the cruise port recently opened as Sparkman Wharf, where some of the city’s best chefs operate takeout spots from colorful shipping containers. I’m having dinner with a family friend, Ray Chiaramonte, an urban planner.

“I never get tired of coming downtown and seeing all that has changed,” Chiaramonte says as we walk toward the water. “This area is where we would come and watch the banana boats unload. Now it’s the center of one of the largest downtown redevelopment projects in the country.”

I stop at Swigamajig, a restaurant run by four-time James Beard Award semifinalist Jeannie Pierola. I order a Tarpon Springs charred octopus Greek salad. It takes its name from a nearby coastal town that’ s known for both its sponge-diving and for boasting the nation’s highest percentage of Greek-Americans.

I ask Chiaramonte what he loves most about Tampa, and I find his answer remarkably similar to my own. “I was always proudest of the ethnic mix,” he explains. “We have a lot of work to do, but Tampa—with its history of all kinds of people working together making cigars 100 years ago—built a culture that was more accepting and diverse than many other Southern cities.”

I say goodbye and stop for a nightcap back at the Haya’s lobby bar, Flor Fina. I flip through the extensive rum list, but then I catch sight of someone down the bar sipping out of an elaborate ceramic peacock, which I simply can’t pass up. It’s a classic Painkiller, a tiki drink made with two types of rum, coconut, pineapple, orange and lime. It reminds me a bit of Ybor City itself—something recognizable, and a bit kitschy, gussied up for a new audience.

When I was a kid, the Hillsborough River always loomed large for me, snaking as it does through the mangrove swamps and cypress forests of the city’s rural outskirts, then through state parks and suburbs, before eventually emptying out into Tampa Bay. In sixth grade, area students attend a riverside camp called Nature’s Classroom, where they learn about native species. I can trace my love of birdwatching to the ibises, egrets, herons and cormorants that I saw dipping and splashing and hunting in these waters. These days, the river acts like a ribbon, connecting some of the most progressive and exciting neighborhoods along downtown’s western edge.

I start the morning at Oxford Exchange. It's a restaurant, shop and coworking space in a whitewashed-brick building that was constructed in 1891 as a stable. In the 1920s it was transformed into a shopping arcade. In the glass-roofed conservatory, I order lemon ricotta–topped pancakes and an iced caramello—local Buddy Brew coffee sweetened with housemade caramel. In the attached shop, I pick up an embroidered patch depicting my next stop, the University of Tampa, just across the street.

The campus is home to the city’s best-known building, the former Tampa Bay Hotel. The property was founded by railroad tycoon Henry B. Plant in 1891 and is topped with minarets that gleam silver in the sunlight. I head into the building, which now houses the Henry B. Plant Museum. It is a time capsule of the Gilded Age that reveals not only the way people lived back then but also the way they traveled—the kinds of hotel spaces they lingered in, the souvenirs they brought back in their trunks from exotic adventures.

Outside, in Plant Park, I stop in front of an impressive pre–Civil War cannon that’s only the first sign of the hotel’s military legacy. During the 1898 Spanish-American War, the building served as an HQ for U.S. Army officers. Colonel Theodore Roosevelt ran his Rough Riders through horseback drills nearby, while Clara Barton organized hospital supplies inside. I cross over the Kennedy Boulevard Bridge and continue north along the Tampa Riverwalk, a walking and biking path that skirts the bank of the river.

In front of the Tampa Museum of Art, I stop to snap a photo of Spanish sculptor Jaume Plensa’s Laura with Bun. It's a 23-foot-tall cast-iron head of a young woman with her eyes closed peacefully. It looks as if she’s soaking up the Florida sun. At the northern terminus of the park sits Armature Works, a 1910 streetcar warehouse that now hosts a food hall.

It’s wildly popular, and it encapsulates a new way of thinking in this city. Tampa, to me, has always represented an insatiable drive for expansion: superhighways, new chain restaurants (Hooters and Outback Steakhouse were both born in the area), gated subdivisions that pop up like weeds. Not to get overly sentimental, but places like Armature Works almost feel contemplative to me. It's as if we all took a breath and decided to finally respect the spaces we already have instead of churning out new ones. For lunch, I grab a patio seat at Oak & Ola, chef Anne Kearney’s restaurant, and order the colorful lobster and saffron pasta.

I complement the dish with a super-refreshing Child’s Play cocktail. It's a zingy mixture of Tito’s vodka, grapefruit, lemon, seltzer and aquafaba (that’s chickpea water, for the uninitiated) for a bit of foaminess. I stop myself at one drink because I have an active afternoon ahead.

At the river’s edge, I meet up with Mike Conlee. He's an owner and guide at Urban Kai, which offers kayak and stand-up paddleboard tours of the river.

We lower ourselves into kayaks and slip into the water. We retrace my steps along the Riverwalk in reverse. “The river is somewhere around 27,000 years old and is the water source for most of Tampa,” Conlee tells me as we paddle southward, toward the bay. “The river’s headsprings start at the Green Swamp and flow 60 miles, ending in Downtown Tampa.” Because the water gets brackish in these parts, we keep our eyes peeled for manatees, dolphins and rays, as ospreys fly overhead. Conlee points out the docked José Gasparilla II, a pirate ship built in 1954 and used ever since in Tampa’s annual Gasparilla festival. Based on the legend of a pirate named José Gaspar who supposedly invaded the area (there’s no proof he actually existed), this Tampa Bay tradition is a celebration similar to Mardi Gras that has been going strong since 1904. Residents invade the harbor in their boats and line the streets for raucous fun. I’ll always associate the day with sweating inside my wool marching band uniform. As we glide toward the mouth of the river, Conlee points up at the skyscrapers downtown. “It’s such a unique way to see the city, since we are mostly surrounded by water here,” he says. “And it’s definitely the best way to catch a sunset.”

I’ve worked up an appetite (and probably sore arms tomorrow). I summon a rideshare to take me to dinner in Seminole Heights. The area is an eclectic jumble of early-20th-century bungalows and stripmalls that hides some of the most exciting restaurants in Florida. At the acclaimed Rooster & the Till, James Beard Award nominee Ferrell Alvarez casts a wide net for culinary influences to sprinkle through his sharable plates.

Vietnamese nuoc cham adds a citrusy tang to cobia collar. A Mexican-inspired birria lamb-neck quesadilla is served on a lamb-fat tortilla. The pork belly comes with corn pudding, tasso ham XO sauce, and turnip chow chow. It is the kind of dish that a Southern grandmother and her hipster progeny might both love. Instead of grabbing dessert, I walk a few blocks to Mandarin Heights. It's a mid-century-style cocktail lounge with a breezy outdoor terrace where influencers pose for photos in a bathtub surrounded by framed flamingo portraits.

It’s a whimsical affair, but the drinks are deadly serious. The Holè Molé mixes mezcal, tequila, and Aperol with green poblano chile, roasted corn, red bell pepper, mole, cilantro, lime and (again) aquafaba. It might technically qualify as a salad. It leaves me feeling good enough to maybe think about a bathtub influencer selfie of my own.

Just across the bay from Tampa proper sits peninsular Pinellas County. Its western shore is lined with some of the best beaches in the nation. In recent years, something even more exciting has been happening in its biggest city, St. Petersburg. Once nicknamed “God’s waiting room,” St. Pete still has the trappings of a retirement mecca—you can’t miss the world’s largest and oldest shuffleboard club. But the area is also developing more than a few urban bona fides. Visitors will find a gallery-filled warehouse district, a slew of microbreweries, and a pedestrian-friendly main street named Central Avenue. It is lined with street art and indie businesses that would fit in in Austin or Nashville.

A cross-bay ferry began running recently, but I’m heading over to St. Pete early, so I opt for a rideshare across the Sunshine Skyway Bridge, which looks like a twin-masted ship and practically feels like an aquatic safari. Keep your eyes trained toward the horizon and you’re almost guaranteed to see a pod of playful dolphins. I drop my bags at The Vinoy Resort & Golf Club, Autograph Collection, a newly refreshed Mediterranean Revival gem that opened its doors in 1925. The grand building is awash in a dusky coral color that reminds me of either flamingos or peel-and-eat shrimp.

Friends from the area have told me that the city’s best new brunch can be found, oddly enough, at the Johns Hopkins All Children’s Hospital.

The only thing more gorgeous than The Library’s book-lined space is the pork-belly Benedict with fried green tomatoes and creole fondue served on a house-baked biscuit by executive chef Rachel Bennett, a semifinalist for the 2019 James Beard Foundation’s Rising Star Chef award.

Cafeteria Jell-O it’s not. From here, I head toward the reimagined St. Pete Pier, which opened in 2021.

I used to go to the old pier, a 1970s inverted pyramid, for family brunch buffets. The latest incarnation is a minimalist thing of beauty that truly pays homage to the nature surrounding it. I walk under an aerial installation by Tampa-born sculptor Janet Echelman called Bending Arc, which calls to mind a fisher’s cast net catching a breeze before it falls to the water’s surface. The piece was made by tying 1,622,528 knots in 180 miles of twine. I continue along the water, dipping my feet in at Spa Beach, before heading to the Tampa Bay Watch Discovery Center.

The space is an aquarium and science museum dedicated to reviving and revitalizing the bay. With the help of volunteers, the nonprofit installs shell reefs and oyster reef balls (each bivalve can filter up to 50 gallons of seawater a day) and replants marsh grass, which supports life-sustaining mangrove ecosystems.

Now, from the pier, you can regularly see manatees, dolphins, rays, and sharks. But there’s still work to be done. A sculpture of a wave at the museum is made from 1,500 plastic bottles—the number Americans use every second.

I need something to help digest that hard fact, so I make for the pier’s rooftop bar, Pier Teaki, for a spiced fish spread with plantain chips and a Hemingway daiquiri.

Although the pier might be a bit polished for Papa’s dive bar tastes, I’m sure the sun and all those fish teeming in the bay below (thanks, Tampa Bay Watch!) would have eventually won him over.

Next up, I want to explore one of the institutions that has turned St. Petersburg into a surprising museum capital. The past decade alone has seen the opening of the Chihuly Collection, the Imagine Museum, the James Museum of Western and Wildlife Art and the Museum of the American Arts and Crafts Movement. Perhaps the most attention-grabbing is The Dalí Museum, which houses more works by the Spanish Surrealist than any collection outside Europe.

The building calls to mind the order-meets-fantasy vibe of many of Dalí’s works: It’s a giant concrete box, seemingly under attack from an amorphous entryway/skylight that wraps around it like a parasitic blob. Inside, the lobster-shaped telephones and paintings of men hatching out of eggs convince me that Dalí, a lover of the unusual, would feel right at home in the state that spawned the Florida Man meme.

After a swing through the gift shop (for all your color-changing-melting-clock-mug and Dalí-mustache-corkscrew needs), I grab a treat at The Hyppo, a Florida mini-chain of ice pop shops born—like the state itself—in St. Augustine.

The flavors read like a regional culinary history: key lime, guava, muscadine (a Southern wild grape), mojito and even datil, a tiny, super-spicy, Florida-grown chili pepper. I opt for a guava cheesecake pop, which tastes a bit like the pastelitos I grew up eating in Ybor City, and head down Central. As I stroll the street art–filled corridor, past block after block of new cultural institutions, the pop triggers in me an odd sensation of nostalgia and, I suppose, more than a little bit of regional pride. Proust can keep his memory-sparking madeleines; on the humid Gulf Coast, an icier treat does just the trick.