Your insider’s guide to Gasparilla Pirate Fest

Pirates invade Tampa during the annual Gasparilla Pirate Fest — Photo courtesy of Keir Magoulas | Visit Tampa Bay

Shake off the winter blues with a visit to Tampa, Florida, for the annual Gasparilla Pirate Fest. Held in January, this annual celebration of all things pirate attracts hundreds of thousands of like-minded revelers to the city.

The legend and history of Gasparilla

The stuff of every child’s imagination, this annual event celebrates José “Gasparilla” Gaspar, a Spanish naval officer who turned to a life of piracy in the late 1700s. According to legend, Gaspar and his buccaneers robbed and pillaged for almost 40 years aboard his stolen flagship, the Floridablanca.

His exploits came to a tragic end when, to avoid being captured by the schooner USS Enterprise, Gaspar wrapped himself in the ship’s anchor chains before throwing himself overboard, shouting, “Gasparilla dies by his own hand, not the enemy’s!”

Since 1904, residents of Tampa have celebrated the legendary pirate José GasparSince 1904, residents of Tampa have celebrated the legendary pirate José Gaspar — Photo courtesy of Tampa Bay History Center

Since 1904, the residents of Tampa Bay have adopted the legend as their own and enthusiastically taken part in the Gasparilla Pirate Fest. Downtown hotels, restaurants and nightclubs, as well as those in the nearby Ybor City and SoHo neighborhoods, are packed with revelers dressed as pirates. All over the city, pre-parties and post-parties will last the entire weekend.

The Gasparilla Pirate Fest is a series of events that takes place on the last Saturday in January. You can attend one or all of the events, but it can take a little planning to enjoy the day fully. Below are some pro tips to help you make the most of your experience.

Pirate invasion

Pirates ready to jump ashore during the Gasparilla Pirate InvasionPirates ready to jump ashore during the Gasparilla Pirate Invasion — Photo courtesy of Keir Magoulas | Visit Tampa Bay

The day begins at 11:30 a.m., when a fully rigged replica of the Floridablanca, thronging with thirsty swashbucklers, appears at the mouth of Hillsborough Bay. As the ship makes her way to “invade” downtown Tampa, she is joined by hundreds of chartered and private vessels — a colorful and impressive flotilla that ultimately docks at the Tampa Convention Center. After an intense volley of cannon fire, the pirates take over Tampa, and the mayor hands over the key to the city.

One of the best ways to watch the invasion is to join the flotilla! Try sailing in style on the Yacht Starship or hitch a lift on the Pirate Water Taxi. You also can rent your own boat, but this option is not advised unless you are an experienced skipper who can navigate a crowded waterway.

Another way to take part is to buy a ticket to the Gasparilla Invasion Brunch. This option offers a delicious buffet to enjoy while you wait for the pirates to arrive at 1 p.m. While it’s a little pricey at $140 per person, the benefits are a front-row seat to all the action and a full belly before the partying really gets started.

A third option is to arrive early to find a spot with a good view of the bay. Options include along the Tampa Riverwalk in front of the Sail Plaza, on the Harbor Island Bridge, or on Harbor Island in front of American Social and Jackson’s Bistro.

Parade of Pirates

Generous pirates celebrate by awarding their booty to eager parade-goersGenerous pirates celebrate by awarding their booty to eager parade-goers — Photo courtesy of Ye Mystic Krewe of Gasparilla

The second act to the day’s events is the Parade of Pirates that takes place from 2 p.m. to 6 p.m. Consisting of more than 100 elaborate floats, the rowdy procession follows a 4.5-mile route along scenic Bayshore Boulevard and through downtown Tampa before ending at Curtis Hixon Waterfront Park. In 2021, an estimated 200,000 were in attendance, making Gasparilla the third-largest annual parade in the United States.

It’s important to claim a good spot — not just to enjoy the parade but to secure your share of the pirate’s booty. To celebrate their capture of Tampa, the pirates generously share their wealth by flinging colorful beads, coins and other exotic treasures to the crowds. If beads are your jam, you’ll want to make your way toward the beginning of the parade route to ensure the best booty selection.

If you don’t want to stand around for hours waiting for the parade, you can buy bleacher seats. If you go this route, plan ahead because these seats can and do sell out.

Pirate Fest

Another parade-viewing option is to catch it at the end of the route in downtown Tampa, where the Pirate Fest will be in full swing. You can pass the time with live music and plenty of food and drink vendors to keep you fed, watered and entertained while you wait for the parade to arrive.

The 2023 Pirate Fest is being expanded to include locations at MacDill and Curtis Hixon parks, with festivities scheduled to last until 8 p.m. If you choose this option, be forewarned: You won’t see the parade until about 4 p.m., so pace yourself if you want to avoid too many visits to the portable toilets.

Dress the part

Dressing up like a pirate is half the fun at the Gasparilla Pirate FestDressing up like a pirate is half the fun at the Gasparilla Pirate Fest — Photo courtesy of Keir Magoulas | Visit Tampa Bay

It’s not just the invading pirate krewes that like to dress up. Locals will use almost any excuse (this being the best one) to dress like pirates too. If you really want to get into character, one way to get outfitted is to check out Pirate Fashions. The owner, Tiger Lee, is dedicated to transforming ordinary landlubbers into authentic pirates. Whether you buy online or visit his Tampa location, you can find everything here to outfit the modern pirate from head to toe.

How to plan your trip

If you’re coming in from out of town, the best place to stay is downtown. There are plenty of hotels to choose from, only steps from the action. For example, the Tampa Marriott Water Street is adjacent to the site of the Pirate Invasion. Slightly less expensive is the Hotel Tampa Riverwalk, located along the parade route and next to the Pirate Fest. Prices will decrease and availability will increase farther out from the event. Book early as occupancy rates will skyrocket as the date nears.

If you need to travel downtown, your best option is to take a cab or shared ride service from where you are staying (watch out for surge pricing), or you can take advantage of the park and ride options offered by the city bus system. Parking at the event is not advisable. It is expensive, hard to find and will almost certainly include a lengthy walk.

What about the kids?

As one might expect from an event whose major sponsors are the Seminole Hard Rock Hotel and Casino, Bud Light and Captain Morgan rum, there is a lot of adult behavior at Gasparilla. While it is perfectly safe to bring the kids, they might have more fun at the PG-rated Gasparilla Children’s Parade, held the week before.

But that’s a story for another day. Aaarrgh!

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