Founded on the fumes of fat cigars and pirate’s booty, Tampa’s always been a city of old-school indulgences. At the turn of the 20th century, cigar factory workers turning out tightly rolled stogies in Tampa’s Ybor district put “Cigar City” on the map. And the entire town still goes wild when swashbucklers galore wash ashore during the century-old Gasparilla Festival, held each winter in honor of Spanish buccaneer Jose Gaspar, who amassed scores of treasure trolling Tampa’s waters. But in the last few years, cosmopolitan hoteliers, James Beard nominees, and neighborhood revitalizers have transformed this history-heavy city by the bay into a must-visit gulf coast gem on the cultural cutting edge. The hallmark of Tampa, though? It never forgets its roots.
Day One
Morning
Bustling with brewpubs, eclectic eateries and shops, and craftsman-style bungalows, the Seminole Heights neighborhood is a good place to start your Tampa tour. Skip the chain pancake places and head to Three Coins Diner on Nebraska Avenue for breakfast. The diner, open 24/7, exudes an old school, greasy-spoon charm with vinyl booths and bottomless cups of coffee served on Formica countertops. After filling up on a feta cheese omelet and cheap caffeine, head west a few blocks to Florida Avenue to get your boutique and antique shopping on. Stop by the Seminole Heights General Store to stock up on everything from deli meats and locally produced honey to live fish bait and antique teacups. At Sherry’s Yesterdaze down the street, the pastel purple and Pepto-Bismol pink façade hints at the colorful racks of vintage clothing inside. For more shopping, head to the newly opened Vintage Post Marketplace, where fine china and kitschy knick-knacks mingle on the shelves of antique and consignment furniture.
Afternoon
Photo courtesy of Gasparilla Pirate Fest/Event Fest, Inc.
Not content with three James Beard nominations in the last three years for his Seminole Heights hot spot The Refinery, chef Greg Baker opened his second restaurant Fodder & Shine in early 2015. Head here for lunch to try inspired takes on Cracker cuisine, the down-home grub of early 1900s Florida settlers. Think grilled frog legs, from-scratch biscuits, smoked mullet, and pilau (pronounced per-loo)—a rice cake smothered in a rich tomato gravy and topped with sausage, shrimp, and a fried egg.
Ready to work off those biscuits? Then stroll, sprint, or skate down Bayshore Boulevard in South Tampa, home to the longest continuous sidewalk in the world—and definitely the only one to be invaded by pirates every year. If you’re here in January, line up a lawn chair along Bayshore to witness the ribald festivities and eager—though poorly aimed—bead throwing of the krewes that march in the annual Gasparilla Parade (pictured above).
Evening
Photo courtesy of Visit Tampa Bay
Move from the bay to the river at Downtown Tampa’s Riverwalk. A wide pedestrian thoroughfare studded with small parks and green spaces that snakes alongside the Hillsborough River, the Riverwalk has revitalized Tampa’s once-ghostly downtown waterfront district. Make a pit stop at the Curtis Hixon Waterfront Park for prime views of the University of Tampa’s Moorish architecture and striking minarets across the river. And yogis, take note: free yoga lessons are offered at the park many evenings.
Go from “om” to “nom” with tapas and drinks at the nearby downtown hot spot Fly Bar. With names like “Rosé All Day” and “Poolside in Mexico,” the cocktails shaken up here are “relax and unwind” in a glass, and they pair perfectly with the kitchen’s sophisticated takes on classic bar food, like nachos topped with succulent Cuban pulled pork or rabbit tacos. This isn’t a beach bum’s Tiki bar, though; warm wood paneling and steam-punk-inspired steel accents keep things hip yet comfortable. Head up to the roof deck for a spectacular sunset over the downtown skyline. 
Photo by Holmes Palacios, CC-BY
Day Two
