In the early 1800s Jose Gaspar terrorized the Florida coast. Stealing fortunes from ships, the pirate up and vanished after a confrontation with the US Navy. Legends say that sensing a defeat, he tied himself to an anchor and jumped into the ocean. Regardless of the truth to this mythical tale, Tampa has commemorated Gaspar’s shenanigans with the annual Gasparilla Pirate Festival since 1904.
I’ve wanted to visit for several years, but 2026 marked the first where my schedule overlapped with the festivities.
Joining me was Rebecca, who was also traveling down from DC, and Courtney, who was flying up from South Florida.
It was a bitter January in Virginia and Rebecca and I were anxiously awaiting the balmy Florida air. Our journey started as I hopped on the metro toward National Airport. When we crossed the Potomac, it was completely frozen over.
After no wait for security, I was surprised to bump into my sister at the aiport! She was flying up to JFK, but a delayed flight led her and her friend Michelle to meet Rebecca and I in the airport.
There’s no better place to start a trip than the Capital One Lounge (not an ad). You should know how I feel about these places! Unfortunately, everyone else had the same idea. What was quoted as a 25 minute wait ended up being about 50 minutes.
Author’s Note: In all fairness to the Capital One Lounge, you can technically reserve tables in advance. This is something we discovered the day before and there was no availability.
The one at DCA, technically a Capital One Landing, is set up a little different than the one at Dulles. In lieu of a buffet line of food and a separate bar, everything is ordered from the table via QR code. It’s innovative and incredibly convenient.
After ordering doubles of all the small plates on the menu, we had a table full of food in just a few minutes.
As expected, the food was excellent! Standout items to me were the patatas bravas and steak. I also really enjoyed my espresso martini.
Rebecca and I wanted to try as many of the cocktails as possible, which showed us the downside of table-side ordering. With the lounge packed to the brim, everyone was ordering drinks. We ended up waiting about 30 minutes for another drink before bailing to make our flight.
Thankfully, our gate was right around the corner. While we were the last ones on the plane, we still made it!
Before we knew it, we were taking off over a snowy Washington and turning south over Northern Virginia.
The flight was relatively uneventful. I spent much of it watching The Hunger Games Catching Fire via American’s in-flight entertainment. Between the fading cocktail buzz, entertaining movie and seat next to one of my best friends, the flight flew by.
Before I knew it, we were circling the Tampa skyline and preparing to land.
Once on the ground, we were greeted by the airport’s Gasparilla Bar (very fitting) and a giant flamingo in the main terminal building.
I’m not really sure why she’s here, but apparently her name is Phoebe.
Above is a photo of Rebecca next to her for scale.
From there, my friend Courtney and her grandma picked us up and took us to their townhouse where we’d be staying for the weekend.
At this point it was basically 1 a.m. so we all retreated upstairs and fell asleep.
Morning came quick and we found ourselves at Armature Works on the northern end of the Riverwalk.
As previously stated, we had dreamed of coming to Tampa to escape the north’s bitter cold. But Tampa was in a cold spell. On the day of Gasparilla, wind chills were as low as the mid-twenties.
Like we did, you might be thinking that’s at least better than the negative digits D.C. was facing. But no, 20 degrees is still cold. Very, very cold.
I will say, while the cold was miserable, we made the best of it and still had a great time.
We grabbed coffee from Cafe Hey and took a few minutes to explore the area.
As always, Armature Works was very nice, but I was surprised to find the area around it so barren. There were a bunch of seemingly abandoned warehouses and an air of decay. I didn’t love it.
But enough of that and onto the pirate festivities!
Courtney’s family was very kind to drop us off by the Publix on Water Street.
Unlike the area by Armature, this newly developed neighborhood is gorgeous! It has chic high-rise apartments and architecture, fancy restaurants, and most importantly, tons of people.
Publix supplied us with a gallon of water before we started the journey to our seats. Courtney’s family got us these reserved bleacher seats along the parade route which definitely amplified the experience.
To get to them we had to walk about a mile of the parade route.
We were optimistic on the walk down. With all the Gasparilla festivities, the sun fighting the clouds and the Tampa Bay on our left, we convinced ourselves we would be facing a warm afternoon.
There were a ton of partygoers along the street, many who were carrying beverages. Had it been about 20 degrees warmer, it would have been a perfect vibe.
A few of the mansions along Bayshore were throwing house parties while others had hired their own security. At first it seemed a little ridiculous, but after witnessing the insanity of Gaspy, it made sense.
The parade route housed a few very elaborate corporate booths. I’m sure you could buy a ticket to some of them, but it was fun to walk by. This pirate ship sponsored by Captain Morgan’s rum was my favorite.
Once we found our seats, we had a little under half an hour before the parade. We took some time to admire the bay and grab some photos before going to grab some food and another drink.
The parade started around 2:00 p.m. led by Budweiser’s Clydesdale Horses
I’ve never been to Mardi Gras, but I feel like they have to be similar vibes. There were dozens of pirate themed floats with various Tampaians (?) accompanying them. Beads were flying left and right and drinks were disappearing from everyone’s cups.
Had it not started raining, we would have had the perfect afternoon.
Remember when I said our spirits were high? While with a threatening gust of wind, a wave of rain drenched us.
The temperature plummeted ten degrees as we joined a mass exodus of people trying to leave the seating area. Once out, we booked it toward Counter Culture, a nearby restaurant. Thankfully, we had a reservation. There had to be a hundred people attempting to escape the rain and getting turned away from the overwhelmed hostesses.
If you do decide to partake in Gasparilla, I think a dinner reservation near where you’ll be sitting is essential. This truly saved us.
The restaurant had delicious, if pricey foods. I was able to grab a cider from Keel and Curley, a cidery/winery I love in nearby Plant City. My main dish was this excellent cauliflower dish.
Drained from the cold and the insanity of the day, we ended the night by grabbing a drink at the neighborhood clubhouse before heading to bed.
The next morning started with a walk around Courtney’s grandma’s neighborhood. Looking at these photos now, I genuinely can’t believe it was in the thirties!
The neighborhood had a great view of the Tampa Bay, Courtney’s cousin even said that she’d seen dolphins there before.
One of the neighbors had a Gasparilla display on their front porch, but the poor pirates looked a little hungover when we walked past.
After a quick brunch back at the neighborhood clubhouse, we went over to Hyde Park to check out the farmer’s market.
It turned out to be more of an artisan market, similar to the one hosted at Orlando’s Lake Eola Park. These are cool in their own accord, but Florida has such incredible produce. I’m always a little disappointed to not see an abundance.
Nevertheless, it was cool to walk around and see what everyone was selling!
We grabbed coffee from Buddy Brew Coffee, a local coffee shop in Tampa, and turned to browsing the shopping center’s permanent tenants.
As you can probably tell, it was still cold. The air temperature was below 50.
As we were leaving the village, I caught this cool view of the Tampa skyline.
We went back to grab our things from Courtney’s grandma’s house.
On the way to the airport, to circumvent the airport prices, we grabbed dinner at Walk Ons. The restaurant brings in local brews, so I tried a delicious Orange Blossom Pilsner from a local brewer.
After that it was back to the Tampa Airport…
…and goodbye to Phoebe.
Here’s Rebecca saying goodbye to the Gasparilla Bar that first welcomed us.
Now, Rebecca and I love a good deal. When we found the chance to save a couple bucks on the flight home, we jumped on it. Even if it meant stopping in Miami.
The 30-minute flight had some great views of Florida as we flew south.
We passed over the suburbs of Tampa, Sanibel Island and the tip of Naples before turning east over the Everglades.
Still seated together, Rebecca and I tried to watch first part of the Grammy’s on American’s live TV. There were SO many ads that we were already approaching South Florida before they gave out an award.
As we circled over Southern Florida, I saw a cruise ship out in the ocean.
The approach into Miami has to be one of the coolest landings I’ve ever done.
We had about 45 minutes in the airport which meant just enough time to get empanadas from Half Moon Empanadas and walking to our new gate.
Before long, we were back over the Miami skylineand leaving the Florida coastline as we headed north.
We flew over Grand Bahama Island as the lights along the Florida shore disappeared.
I’m not sure why, but the flight took a strange route over the ocean. We didn’t cross back over land until coastal North Carolina.
We landed at National Airport and I was back home around 1:30 a.m.
Overall, Gasparilla was great, thanks in large part to the company I was with. I think I would have enjoyed the festival itself a bit more if it was warmer, but that’s at no fault to anything but fate.
I’ll be looking forward to visiting another year. We had such grand plans to kayak at the springs, lounge by the Gulf and swim in the pool, but all were thwarted by the cold.
I guess that only means I need to go back!
Turquoise Skies 