Tampa’s Gasparilla Pirate Festival

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January 27, 2017: Flying as a Pirate

Ever since I was 8, I have always wanted to go to Tampa because my parents bought me a Tampa Bay Buccaneers paper pad. I got my wish on January 27th when I went on a weekend trip to the Gasparilla Pirate Parade, the world’s largest pirate festival.

While there are occasional direct flights to Tampa, they are rare and did not leave when I needed to. Indirect flights were also very expensive. Instead, I found a $170 roundtrip flight to Orlando which is only about 75 minutes away. My flight there was on American and the return was on Frontier.

Earlier in the week, per tradition the Ye Mystic Krewe of Gasparilla stormed the Mayor’s office demanding the Key to the City. The mayor refused, so the pirates promised to return on Saturday with a full-blown invasion… The stage was set.


In order to fit in, I borrowed a pirate costume from a friend at the gym. It ended up being way more elaborate than I was expecting- it even had a wig. It was so bulky that I couldn’t fit it with all my clothes into my budget-airline approved carryon bag. So in order to save $40 and to have a little fun, I decided to wear the costume onto the plane there.

I walked into the airport in the full pirate costume and got a ton of stares. People were clearly taking pictures, but nobody said anything. I then walked over to the international terminal for more fun. I got some great reactions from a Qantas flight to Australia and got the weirdest states from a Philippines.

Eventually I boarded my Orlando flight where one person recognized that I was going to Gasparilla. Otherwise, the flight was unremarkable.

January 28, 2017: Gasparilla

Once in Orlando early on Saturday, I rented a car and headed straight to Tampa. The drive took an hour to reach my friend Jon’s house.

Once I got to his house, I immediately took a 2 hour nap.

It was now 10am and time to head out. After getting a quick breakfast, we drove the rental car into downtown Tampa passing swarms of people dressed in pirate outfits. It was unseasonably cold- around 60 degrees so people were more bundled up than the previews online showed. We blasted the theme song to Pirates of the Caribbean. It was epic.

We parked at the Tampa General Hospital (a cheap and central place to park) and then headed into the madness. We walked over toward the Convention Center. Along the way, we passed by thousands of already-drunk pirates! One guy even had a pet bird!

The convention center was blocked off, so we then headed to a waterfront bar with views of the harbor. Hundreds of boats were swarming- most flying the Jolly Rodger. Some of the boats drove over towards us and threw out beads to the cheering crowds.

Right at 1pm, a huge pirate ship with tons of flags named the Jose Gasparilla sailed into the harbor. It was staffed by hundreds of pirates from Ye Mystic Krewe of Gasparilla, the organizers of the festival. The Jose Gasparilla fired its cannons! Boom!

The pirates landed their ship at the Convention Center where the mayor handed them the keys to the city. They then walked over to buses to take them to the parade staging grounds.

The party then moved to Bayshore Boulevard, where 400,000 people would cheer on the pirates in a parade. The parade started around 2pm and had more than 50 pirate-themed floats throwing beads. Elected officials also rode floats including the mayor, city council, Florida state officials and US Representatives.

In addition to cheering for beads, Jon and I got to witness the humanity of Tampa. One super drunk white lady called herself “Ghetto Barbie” and told a black boy that only his sisters can get beads. Another group of people “reserved” an enormous amount of space and dozens of other people got in a fight with them over the space. Another guy offered to give a beer to anyone who would sing the national anthem. A bunch of people did. Someone else asked me where my beer is. When I replied “I don’t know, where is it?” He then gave me a beer.

By 4pm, we had seen tons of floats blasting music and collected many beads. It definitely helped to be tall at this parades. We then walked back to the car and drove away from the parade zone.

Since we were both really hungry, we got cake at Wright’s deli. I got a pineapple cake and it was amazing.

January 29, 2017: Exploring Tampa

The next day, I got to do a little Tampa sightseeing. My first stop was the Cigar City Brewing Company, one of the top breweries in the Southeast. I was on a tour with a couple from St. Louis who were very confused why there were so many people at the bars in pirate costumes.

After the tour, I headed over to Ybor City, the historic cigar-making district. I got lunch at the Columbia Restaurant, a famed Spanish Restaurant that claims to be the oldest restaurant in Florida. Although it was a 2-hour wait, I was able to sneak in immediately for a seat at the bar. Their soup is incredible.

Ybor City now appears to be more of a night street than a day street, but there is a fantastic history museum run by the State of Florida. Ybor originally was built for the cigar industry. No single company ever dominated the town, but there were over 50 factories at one point. Florida’s first sizable Cuban population lived in Ybor and that group played a major role in backing the Cuban war of independence from Spain. Jose Marti himself visited Ybor at least 20 times. Ybor also had Florida’s first Jewish community.

Eventually the cigar industry faded and Ybor became decrepit only to be reborn decades later as a bar district. Today’s Ybor is Tampa’s most popular place to go out. There are a few small cigar factories catering to tourists, but there are many more bars.

It sort of looked like a cross between Abbot Kinney and Bourbon Street with way less people.

It was then 3pm and time to head back to Orlando. On the way back I stopped briefly in the shockingly large town of Lakeland.

Final Thoughts:

Gasparilla is wild. The people go as crazy as any other big festival, but the pirate theming adds a fun unique element to the day. As for Tampa, I really like this city. It seems to have more charm than the other cities in Florida.

I definitely hope to return again one day. There is still so much left to do including St. Petersburg, Clearwater, Bradenton,  the sports teams and some of the museums in Tampa.


2 responses to “Tampa’s Gasparilla Pirate Festival”

  1. Sally Lawler Avatar
    Sally Lawler

    How was it going through security with a pirate costume?

    1. brycewcaster Avatar

      No issues, surprisingly!

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