Surprises and treasures: Gaspirilla and beyond
Josh's initial ideas were shaped by comparisons to other cities, but what he found was a revelation.
A vibrant getaway brimming in uniqueness and surprises
Stepping off the plane, I'm hit with a warm Gulf breeze – a sweet relief from Chicago's icy grip. This place tastes different, salty, and warm. As I cruise towards downtown, the sights reel me in. There's Busch Gardens® Tampa Bay with its wild roller coasters teasing in the distance, and palm trees, cool bungalows and murals that pop. It’s got a “we live here and we love it” kind of vibe; everyone is stoked to call it home.
I'm here for Gasparilla Season, a tradition stretching back over 120 years as a playful homage to the area's colorful, albeit mythical, pirate legacy. Every year, the legend of pirate, Jose Gasparilla, comes alive with a theatrical invasion in which the Mayor humorously "surrenders" the keys to Tampa Bay to commemorate its buccaneer spirit and rich maritime heritage. The season is an exuberant display of culture and merriment as the streets thrum with the nation’s third-largest parade, and, music, film, and art festivals. I land amidst the festivities. I see colors everywhere, and people, everywhere. Families line the sidewalks in costumes, pets sport palm-festooned sombreros, and everyone's in high spirits going out, hanging out, eating good food. There’s a vibrant blend of community and tradition that pulsates the atmosphere transforming Tampa Bay into a buzzing hub of creative energy.
During this time, each weekend promises new delights and experiences, truly a spectacle that has something for everyone, such as the Gasparilla Music Festival which fills the air with eclectic tunes, and the Gasparilla Film Festival which casts a spotlight on indie storytelling.
As I start to feel a little hungry, I see a place called The Oxford Exchange, and I decide to grab a bite there. From the moment I walk in, I'm greeted by an upbeat, smiling hostess brimming with positivity. The atmosphere immediately captivates me – an atrium filled with light, cozy reading nooks, and a charming bookstore vibe. When my bill arrives, it's presented tucked inside a hardback book cover, which was pretty rad.
But, Tampa Bay's not just about pirate shenanigans. The waterfront is gorgeous and as a nature nerd at heart, I’m drawn to the tranquility of the outdoors, so following the festival I decide to venture out on a kayaking tour. It’s the perfect tonic to the wildness of the previous day. I paddle out, taking in the serenity around me, and suddenly, I see a gray bulbous form gliding through the waters below. The hairs on the back of my neck prick up as I imagine some beastly sea creature, but then breathe a sharp sigh of relief as I realize that it is, in fact, a snoozing manatee – I’d never seen one in real life! To this day, that sight is one of my favorite memories of all time.
Back ashore, night blends salsa rhythms, rich smells of roasting Cuban coffee, and laughter drifting from historic Ybor City. As I stroll through the vibrant streets, the echoes of Spanish music and the lively atmosphere feel like a familiar embrace. As a Mexican and Puerto Rican, I grew up immersed in rich Hispanic culture so hearing Spanish spoken here resonates deeply. I meet locals over steaming plates of tangy Ropa Vieja stew, hearing stories of the immigrant cigar factory workers who built this quarter over a century ago. And then there are the wild roosters roaming the streets that add a unique quality.
In Tampa Bay, you get a mix of different worlds all in one place – pirate adventures, peaceful nature, and lively streets with a rich history. It's a lot of different experiences, but somehow, it all fits together perfectly.
*Editors note: This article includes first-hand experiences as well as inspirational activities.
A 120-year-old pirate festival I knew nothing about, but quickly became fascinated by.”
Quick fire five
What's your favorite memory in Tampa Bay?
Seeing a manatee while kayaking! That unexpected encounter with such a gentle giant was a moment of pure awe and definitely a highlight of my Tampa Bay experience.
Describe Tampa Bay in three words:
Color. Energy. Roosters.
What's surprised you the most in Tampa Bay?
Gasparilla. Everyone embracing this mythical pirate invasion was both surreal and fantastic.
Describe what Tampa Bay would be like, if it was a person?
Well kept together and they’d be that family member you hear a lot about, and then you actually meet them and you're like, 'Oh, you know, this one person's pretty cool’.
What's a must-try experience or dish in Tampa Bay?
The 'beach blonde' wings at Wicked 'Wiches with their secret sauce. Perfect fuel for a day of exploring!
