In 1868, many Cubans fleeing the violence of the Ten Years’ War ended up in Tampa. They set up cigar-rolling shops in the Ybor City neighborhood, which today is a strip of shops, clubs, bars, and restaurants. Your best bet for cigars is Rodriguez & Menendez Cigar Factory and Store. For Cuban food, hit the Columbia Restaurant, which opened in 1905.
The city’s football team wasn’t named the Buccaneers by accident. Local lore pretends that pirate José Gaspar once stormed Tampa, demanding that the mayor give him the key. This “storming” is reenacted every January at the Gasparilla Pirate Fest, which began in 1904. Public-drinking restrictions are lifted for the day, and thousands line up along Bayshore Boulevard to watch pirate floats and to catch beads flung into the crowds. Tampa residents show their pirate pride all year, hence all the Jolly Roger flags around town.
Bayshore Boulevard is the world’s longest continuous sidewalk. Be careful if you want to take a walk or run along the 4½-mile stretch. There’s little shade, so in the heat and humidity it’s better to run or stroll on the other side of the road in the shade of palm trees. You’ll also be better positioned to gawk at Bayshore’s mansions.
In 1891, railroad man Henry B. Plant built the Tampa Bay Hotel, a grand resort along the Hillsborough River. Plant loved Moorish architecture, so he crowned the hotel with six minarets. Guests included Teddy Roosevelt, Clara Barton, Stephen Crane, and Sarah Bernhardt. The hotel closed in 1932 and became home to the University of Tampa in 1933. Admission to the university portion is free. You can also take a guided tour of the Henry B. Plant Museum.
Tampa is a town of transplants, lots of whom brought their winter clothes with them. Many items from those wonderful wardrobes end up in Tampa’s eclectic vintage and consignment shops. Your best bets are La France in Ybor City and Sherry’s YesterDaze Vintage Clothing & Antiques.
One tourist attraction most guides leave out: strip clubs. Tampa has more than 20 within the city limits. The two most popular, 2001 Odyssey and Mons Venus, are near each other on Dale Mabry Highway.
The place to see and be seen is Bern’s Steak House, which opened in 1956. It’s a classic, as are many of the 7,000 wines in its cellar, with bottles dating to 1827. If you’re not up for the full Bern’s experience or just want something sweet, stop into the Dessert Room, separate from the restaurant, for the chocolate/peanut-butter truffle.
You have two options. First is the Dalí Museum in St. Petersburg—a half hour away—which was born of A. Reynolds and Eleanor Morse’s private collection of Salvador Dalí.The collection includes 96 oil paintings, more than 100 watercolors and drawings, and 1,300 graphic works, photographs, and sculptures. Second is the Ringling Museum in Sarasota, an hour from Tampa and once the location of the Ringling Bros. Circus’s winter grounds; don’t miss the 56-room, bayfront Ca’ d’Zan mansion. Seeing both cities is a daylong trip.
Curious about what the Democrats are doing in Charlotte? Check out our guide to Charlotte.
Jen A. Miller is a travel writer, University of Tampa alumna, and frequent Gasparilla Pirate Festival attendee.
This article appears in the August 2012 issue of The Washingtonian.