Welcome to Pirate Country: A Guide to Tampa

1 Miami isn’t the only Cuban haven in the US.

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.
2 All the Jolly Roger stuff isn’t Pirates of the Caribbean memorabilia from Orlando.

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.
3 That’s one long sidewalk.

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.
4 No, that’s not a mosque—it’s a university.

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.
5 Mad Men yourself.

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.
6 Take it off!

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.
7 Aged to perfection.

Photograph courtesy of Bern’s Steak House.

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.
8 Want weird? Take a drive.

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.