Get Your Groove On: 5 Festivals In Tampa, FL, To Catch On Your Trip

Get Your Groove On: 5 Festivals In Tampa, FL, To Catch On Your Trip
| 5 min read

Affectionately coined “The Big Guava”, Florida’s Tampa is a city that knows how to work hard and play harder. The outgoing Tampanians love having a good old celebration, with an abundance of annual festivals ranging from art festivals to Guavaween, a Halloween event featuring live music and costume parades down the streets, you will definitely find something for both the cultivated and wild side of you. Here are some fun events to experience in Tampa:

1. Gasparilla Pirate Festival - January

A Tampa tradition dating back to 1904, the Gasparilla Pirate Festival is held on the last Saturday of January every year. Pirates are never ones to be boring! Starting off with a bang, the Ye Mystic Pirate Krewe “invades” the sunny shores of Tampa, sailing all the way from Tampa Bay to downtown Tampa on the majestic Jose Gaspar ship. Demanding the city key from the mayor, the mayor has no choice but to oblige under the threats of the one-eyed rogues. Having seized the city, the swashbuckling pirates then proceed to hold a boisterous victory parade through the streets of Tampa, with live music playing in the background, and booze for the crowd. The head of the pirate crew is led by the mythical Jose Gaspar, famed to be a Spanish captain who took over the high seas of southwestern Florida back in the late 1700s. Avoiding capture and spreading mayhem for over four decades, he was finally apprehended in 1821. Some say he wrapped himself with the anchor chains and threw himself overboard, dying on his own terms, while others say he was murdered by U.S Navy crew members. Today, the annual re-enactment draws a crowd of more than 300,000 each year. When the first Gasparilla Pirate Festival took place, the majestic Jose Gasparilla ship was sailed downtown to serve as a reminder of the victory trumped against the evil Gaspar, but the city-wide celebration today has a more light-hearted touch amongst the celebratory parades. Watching the color-loaded ship teeming with scurrying pirates sail beside hundreds of pleasure craft is a sight to see, and it’s definitely not one to miss! The festivities run into the evening, with live music, food, and entertainment for everyone. If you’re still undecided, check out this video shot by a drone that brings you around the event grounds of the pirate invasion in 2016!

Gasparilla Pirate Invasion

Location: Tampa Convention Center

Price: Free

Website: Gasparilla Pirate Festival

2. Gasparilla Music Festival (GMF) - March

Every second week of March, you will hear the familiar echoes of your favorite bands resonating all over Tampa. The Gasparilla Music Festival features both upcoming local bands performing with national headliners. In this festival that embraces the diversity of music, there’s even a kid-friendly alternative to the raving - the GMF Kids Fest, held alongside the main event. Spanning four stages within two days, the performance venues vary from local eateries to public parks. Get a change of environment by raving to the beats in the usually stoic train cabins! The festival was started as an initiative to support local musicians and eateries, as well as to promote the cultural heritage of the Tampa area. Founded by the Gasparilla Music Foundation, the non-profit organization also seeks to provide financial assistance and support for music students studying locally. Several of the featured acts are young musicians who are just starting out. Check out the short trailer of the 2016 Gasparilla Music Festival below for a glimpse of what goes on at the festival!

Gasparilla Music Festival

Location: Downtown Tampa

Price: from 30 USD, children 12 and under free

Website: GMF

3. Tampa Bay International Gay and Lesbian Film Festival (TIGLFF) - September/October

Source: Photo by Wikimedia Commons user Ebyabe used under CC BY 2.5

Started in 1990 by the Friends of the Festival, the non-profit organization originally started with the Pride Film Festival as a fundraiser, before slowly developing over the years into the Tampa Bay International Gay and Lesbian Film Festival that we all know now. Spanning nine days with over 30 independent short and feature-length film screenings, get up close with the filmmakers themselves in intimate Q&A sessions held after the screening sessions. With the support of many local community-based organizations, the festival was able to celebrate “25 straight years of queer cinema”, as quoted from their slogan back in 2014. However, films aren’t the only things you can catch here; you may even see some of your favorite actors and actresses too! The festival in 2015 had Lea DeLaria of Orange Is The New Black gracing the event grounds with her comedy, partnered with live music. As the world continues to evolve with the times, the various social and political changes that are impacting the global LGBT community are brought to attention with the films made by, for, and about said community. Celebrate the compelling cinematic creations here with an open mind, and speak to the filmmakers themselves to find out more about the stories behind their creative works.

Tampa Bay International Gay and Lesbian Film Festival

Location: Tampa Theatre

Price: from 15 USD

Website: TIGLFF

4. Guavaween - October

Guavaween is the largest Halloween event in Tampa, with up to 100,000 people from all parts of the world participating in the energetic outdoor festival. Featuring live bands, dancing, and the famous costume parade, it’s no wonder that it’s such a crowd favorite amongst the fun-loving Tampanians. Held in the historical Ybor City, the nostalgic balance of the old and new is ever so prominent here, where cigar shops who still sell hand-rolled cigars are set beside snazzy nightclubs with vibrant neon lights. Take some time to appreciate the mysterious alleys and lanes shrouded in man-made lights around you. The famous Mama Guava costume contest is one of the highlights of the night. Judges will choose the best costume designs with categories such as best couple design, most original costume, and best-themed costume. Scored on the creativity of the costume as well as the presentation on stage, get your creative juices flowing and you may be the next winner to walk away with 1,000 USD in cash!

Guavaween Tampa

Location: Ybor City

Price: from 10 USD

Website: Guavaween

5. Cigar Heritage Festival - November

Editor's Note: There's no photo available at the time of writing

Join the locals as they celebrate their history and heritage with the annual Cigar Heritage Festival, held in November. Once crowned the “Cigar Capital of the World” in the early 1900s, the booming business of cigars helped to pave the way of the sleepy fishing village transitioning to the blooming city of Tampa that we know of now. Meet some of the world’s greatest cigar makers, and learn the secrets of the trade with live demonstrations on how to roll your own cigar. Sample the finest brands of cigars available. Whether you’re just passing by or a long-time cigar enthusiast, you can make new friends while being entertained by live music from salsa bands.

Cigar Heritage Festival

Location: Centennial Park 1800 E 8th Ave, Tampa, FL 33605

Price: from 5 USD

Website: Ybor City Cigar Festival

Let your hair down!

Filled with entertainment across different platforms, find something that resonates with you; the abundance of festivals available will not leave anyone out. Vacations don’t just have to be about visiting common tourist attractions. Take part in one of Tampa’s festivals, immerse yourself in the authentic local culture, and have heaps of fun!

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Crystal is a curious child, who loves exploring Singapore in her free time with a camera in hand. Her street photography subjects often include unaware strangers, uncommon architecture, and...Read more

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