Gasparilla. Some things are certain. There will be scantily clad pirates and liquid libations. At some point, it is advised to eat some food. Here are some of the top places that are easily accessed along the invasion route.
Oggi Italian Street Food
Like so many of the restaurants on Davis Islands’ main drag, it feels like a sweet neighborhood mom-and-pop, one that would be equally at home on a windy side street in Sicily. The alleyway is filled with charming small tables illuminated by tiny white lights, a funky welded chrome archway and railings setting off the inviting front porch. It’s got real character, something magnified by a staff of Italian-accented waiters with the authentic balance of insouciance and helpfulness. It’s a short menu: antipasti, an array of roasted chicken options, a handful of hearty pastas and some truly excellent cannoli. Prices are a tad high, but considering the quality of ingredients, they seem fair-minded. 236 E Davis Blvd. (813) 252-7778.
Margaritas Mexican Restaurant
Estela’s was a landmark Davis Islands Mexican spot for years, but a few years back became Margaritas Mexican Restaurant. It’s the kind of place to kick back with a margarita (best one: the spicy version made with Sauza Hornitos tequila) and crunch your way through a basket of warm chips. A long list of dinner combos will require a substantial perusal and some cogitation ("hmm, do I want one relleno and one enchilada, and then a chalupa to round it out?"). These are mostly things you’ve seen before in workhorse combinations, with gooey pools of refried beans and scoops of neon-yellow rice. 209 E Davis Blvd. (813) 251-0558.
Jackson’s Bistro Bar & Sushi
Lounge, patio, sushi bar and waterfront dining room of steaks and seafood all spill over this busy station on the downtown cruising scene. It’s got an extensive wine list, plus good views of other people’s boats and condos. On any night of the week, Jackson’s is a fine place to sip, immerse yourself in swank and possibly spot an athlete. The waterfront venue also has possibly the best vantage point of anywhere for the annual Gasparilla Pirate Invasion. And when celebs come to town, they’re sure to drop by. Paris Hilton, Pete Wentz, Ashlee Simpson, Benji Madden and various Playmates have been spotted there. 601 S Harbour Island Blvd. (813) 277-0112.
It opened Oct. 30 and promptly threw a huge Halloween bash: sexy pirates, scantily clad skeletons, lots of those pneumatically enhanced superhero costumes. It was instantly cemented as a destination for Tampa’s youngish party people. It’s burgers and flatbreads and mac and cheese and fairly straightforward American pub food, served in a good-times sports bar setting. Sharing some small plates seems appropriate: A plate of simple grilled chicken skewers sitting on a bed of hummus with a handful of pita chips, beef strip loin sliders with a kicky horseradish sauce and a trio of corn tortillas cradling slow-braised brisket, peppers and a cilantro lime aioli are all appealing, easy finger foods. 601 S Harbour Island Blvd. (813) 605-3333.
Mad Dogs & Englishmen
Co-owner Wilton Morley seems to do things his own way, and that has worked out just fine. This is a family place, a casual indoor-outdoor spot to meet for a pint and a nibble. The beer list favors Britain, the wine list is more global (prices very reasonable, by-the-glass pours very generous) and the servers and bartenders seem to be from all over the place. The menu features British pub staples (fish and chips, chicken curry) with some more eclectic offerings like red Thai curry and innovative housemade ice cream. 4115 S MacDill Ave. (813) 832-3037.
Yoko’s Japanese Restaurant
One of the reliable suppliers is this quiet but busy spot in the MacDill gourmet cluster. Students, professors, military brass and locals fill the small bar, snare tables or sit shoeless at tatami for tempura, bento boxes and clever sushi. 3217 S MacDill Ave. (813) 835-4311.
The POX burger (pickles, onion and the fabled secret sauce), the butterscotch and coconut cream pies — these are things restaurateur Richard Gonzmart brought back to life when he reopened this Tampa original. It can make you nostalgic for a time you never experienced, burgers, skin-on fries, thick shakes (in other words, ballast for when the pirates have overindulged a bit). 1601 W Swann Ave. (813) 308-1925.
Food is super affordable, tacos all under $4, with sides that complete the deal for another $2.50. Then on the bar side, you’ve got come-hither Latin-inspired cocktails that skitter north of $12. So there’s this diner cognitive dissonance — "this is cheap" and "wait, I shouldn’t have another chorizo spice-infused margarita, but I want to." And second, the ordering process is fascinating and really seems to work. Built on the sushi bar idiom, each table has a little ordering chit. Then you pop the blue dragonfly card into the metal holder and a server swings by. 1601 W Snow Ave. (813) 258-8226.