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Best Things to Do for Gasparilla 2020

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Over 100 years ago, José Gaspar led a pirate invasion throughout Tampa that would never be forgotten. In fact, it’d be glorified until the end of time.

You see, when Gaspar died, it was rumored he left a fortune of treasure buried along the coast of Florida. To this day, it still hasn’t been found. 

To keep his memory and the mysterious hunt for hidden riches alive, Tampa hosts the third-largest parade in the United States every year. While drinking lots of rum, of course. If you live on Bayshore Boulevard, you know exactly what we’re talking about. 


Inspired by the legendary Buccaneer, it’s a pirate-themed season that pays homage to our history over three event-filled months. And as it turns out, it’s one heck of a party. 

We’re sharing the best things to do for Gasparilla so you can pick your poison, and drink it too. The floggings won’t continue, but the fun definitely will.

If you can’t wait a millisecond longer to put on your pirate gear, start the season early at the Gasparilla Bash. This annual party kicks off the first of many festivities with cocktails, complimentary hors d’oeuvres, live music, and pirate parlaying. As a guest, you’ll have the chance to score front row seats to see The Black Honkeys and Bus Stop jam out inside the historic Rialto Theatre. You’ll also be contributing to the community by attending this highly sought after soirée. This year the majority of ticket sales will benefit the Boys and Girls Club of Tampa Bay! 

Miss this party and you may have to walk the plank. 

Event Details
🗓 JAN 10 | 7PM–11PM
📍 Rialto Theatre

If you have a miniature pirate in tow, this parade is for you. Every year, the Sirens Krewe, a community made up of philanthropic females, helps organize a G-rated parade for you and your tiny humans. It’s the perfect opportunity for families to dress up in their favorite pirate threads and partake in the fun in a more relaxed, but equally as festive environment. We recommend this event especially if you have youngsters under five, as the main Gasparilla parade can get…dare we say, a bit rowdy. 

Meet us at Bayshore Boulevard to catch the first float. More details here.

Event Details
🗓 JAN 18 | 11AM–7PM
📍 Bayshore Boulevard

Welcome to the main event! On January 25, 2020, Tampa Bay is invited to channel their inner pirate at Gasparilla’s annual invasion. Every year, the entire city gathers along Bayshore Boulevard in full pirate attire as the world’s longest sidewalk becomes a party. Multi-colored beads are thrown from pirate ship floats, food vendors line the streets, and spirits run wildly high. 

This is your chance to partake in the third-largest, rum-infused, parade in the nation. And probably the only time you can scream “arg” on the street and get a solid “ARRRRRG” in return from a stranger. #nojudgementhere

Don’t forget to tag us on Instagram while you’re there – @stufftodointampabay.

Event Details
🗓 JAN 25 | 10AM–8PM
📍 Bayshore Boulevard

Not into large crowds or parades? Spend your Gasparilla with the Downtown Crawlers. This year marks their third annual Gasparilla Barrr Crawl, including three brunch options and drinks at four of the city’s best bars.

For $55 per person, you’ll sink your teeth into brunch at District Tavern, The Patio or Bar Howard. Afterward, you’ll hop on the Downtown Crawlers’ party bus for a free welcome shot at all participating bars. Plus, you’ll get access to exclusive drink specials, food discounts, and you won’t have to worry about waiting two hours for an Uber. 

Save your spot on the bus before tickets sell out! Buy them for you and your crew here.

Event Details
🗓 JAN 25 | 10AM–3PM
📍 Start at District Tavern or The Patio

All aboard! The 2020 Gasparilla Invasion Brunch Cruise is another lavish way to spend your holiday. It departs at 10:30AM out of Channelside and promises an up-close encounter with the Pirate Invasion Flotilla as it departs into the bay.

At $179.95 per person, you’ll get access to a 2.5-hour cruise on the water, a supreme brunch buffet, and two premium alcoholic beverages. Oh, and you can also party with the DJ on the Yacht StarShip’s promenade deck. 

Book your cruise ticket here. Can’t wait to catch you starboard.

Event Details
🗓 JAN 25 | 10AM–1PM
📍 Yacht StarShip Cruises

The wonderful people behind Keep Tampa Beautiful have vowed to do exactly that. One of their biggest cleanup days of the year happens to be the day after Gasparilla. Help them keep our city clean and free of debris! It’s a great way to give back to the community and start your year off feeling good. 

Visit their website for more details about how you can help. Don’t forget to wear sunscreen!

Event Details
🗓 JAN 26 | 7:30AM–11AM

Arggg you ready to get your run on? Because Publix is ready for you to register. The Publix Gasparilla Distance Classic takes place after the parade dust has settled and you’ve finally decided to stop wearing your Buccaneer trousers.

From February 21st–23rd,  you can choose an assortment of runs to participate in, and there’s truly something for everyone. Register for a half marathon, 15k, 8k, or 5k to join the great race.

We’ll see you at the finish line.

Event Details
🗓 FEB 21–23 | 6:30AM–11:30AM
📍 Downtown Tampa

Emerging artists, painted Carmadas, and a stroll down the TBBCA Chalk Walk are just a taste of what to expect as a Gasparilla Festival of Arts guest. In celebration of its 50th anniversary, this year the festival will feature work from more than 250 visual artists and performers.

When you’re done admiring local masterpieces, stop by the Tampa Museum of Art and take advantage of their “pay as you will” admission price. It’s the ideal event for anyone craving an extra dose of inspiration.

Park in the Poe Garage to hop on the complimentary festival shuttle. It’ll deliver you over the bridge and to the park if you’re not into walking.

Event Details
🗓 FEB 29 | 9AM–6PM
🗓 MAR 1 |
📍 Julian B. Lane Riverfront Park

Ask anyone and they’ll tell you that the Gasparilla Music Festival is the highlight of the season. In our opinion, it’s also one of the best things to do in 2020. If you’ve attended in previous years, you might be nodding your head in agreement on the other side of the screen right now. 

For newbies, this 2-day festival brings more than 40 artists to Curtis Hixon’s waterfront park every year. The 2020 lineup includes artists such as Brandi Carlile, De La Soul, Rival Sons, St. Lucia, Curtis Harding, Portugal. The Man, The Word, Anderson East, and more.

Event Details
🗓 MAR 7 & 8 | 11AM–11PM
📍 Curtis Hixon Waterfront Park

The Gasparilla International Film Festival is one of the most cultural experiences the season has to offer. What began as a small film festival in 2007 has now hosted thousands of filmmakers, producers, and actors, in addition to World Premieres, USA Premieres, and Florida Premiere screenings.

In 2020, the festival highlights more than 120 films featuring a handful of celebrities we all know and love, alongside up and coming talent. *Bring on the popcorn.*

Check out UNATION for updates on screenings and events. 

Event Details
🗓 MAR 17–22 | 9AM–9PM
📍 Multiple Locations in Tampa

If you made it to the end of this article, we hope we’ve officially inspired you to watch Pirates of the Caribbean tonight. But before you do, make sure you mark these key event dates on your calendar! You can always follow along with us for more event news on Facebook, Instagram, or download our app (iPhone/Google Play).  

Remember to tag us at @stufftodointampabay for a chance to get reposted! We’d love to be part of your event adventures. 

Happy Gasparilla! 🏴‍☠️

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Melissa Santell

Melissa Santell

Melissa is a Tampa Bay-based lifestyle and food writer, with a serious love for cooking Italian Food, photography, and reading her Aquarian horoscope. Melissa’s work has also appeared on Thought Catalogue, Entrepreneurial Chef Magazine, and Creative Loafing. She is a University of Tampa Alumni and was previously named 30 Under 30 by the Tampa Bay Business Journal. When Melissa isn’t writing, she’s flexing her digital marketing muscles for clients or shooting food photos for her upcoming cookbook. Find Melissa on Instagram at @melsantell.

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