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Gasparilla Children’s Parade Day: Gasparilla Preschooler’s Stroll

Possibly the most adorable event in the world, the Preschooler’s Stroll (launched in 2005) is an opportunity for the under-5 crowd to show their buccaneer spirit right before the main event, the Ashley Children’s Gasparilla Parade presented by Chick-fil-A.

Related: Gasparilla Children’s Parade: Local Parents Share Pro Tips

Gasparilla Preschooler’s Stroll 

What: Participants must be in pirate themed attire and accompanied by adult. While no motorized vehicles are allowed, the little pirates are welcome to ride in a decorated wagon, stroller, tricycle or bicycle. 

When: 1:00 p.m. Saturday, January 22, 2022

Where: A half-mile on Bayshore Boulevard from Howard to Rome.

IMPORTANT: There is a mandatory preregistration for this event. Visit to download an application. No walkups allowed on the day of, so prevent tearful outbursts and plan ahead! Also, if you are purchasing your tickets or bleachers seats with a view to watching this event, please make sure you choose a spot between Howard and Rome! Not all bleacher seating will allow you to view this portion of the stroll.  

“We started this because we had a need to do something fun for the kids too young to participate in the parade itself,” says Maiken Stefany, director of operations for the Children’s Gasparilla Parade.


The stroll is an easy half mile on Bayshore Boulevard from Howard to Rome Avenues and starts at 1:00 p.m. Saturday, January 22. Parents who want their tots to participate must pre-register. No walkups will be allowed on the day of the event. All children must be in pirate or animal themed costume, and must ride in decorated “units,” strollers, wagons or tricycles. No motorized vehicles are allowed. 

 “Parents really get into it,” Stefany says. “Neighborhoods get together and decorate wagons the same way. Parents go all out, some do replicas of ships that are really intricate—fake smoke for cannons, and some light up… the more glitter and beads, the better!” 

Prizes will be awarded for exceptional best in show “floats,” and Stafany says winners are usually offered complimentary bleacher seating for the children’s parade. The parade is intended for children 5 and under, but there are no restrictions on older children who wish to walk and pass out beads.  


The tots (and mandatory accompanying adults) must gather at the for the 1:30 p.m. start time. In recent years, the stroll has been moved away from the staging area for the larger floats for the children’s parade. In 2019, more than 1,000 people participated in this event. 

 “It’s adorable, it really is,” says Stefany. “We only move as fast as the smallest pair of legs can go. We are excited to see it continue to grow.” 

*Photos courtesy of Event Fest, Inc.

Originally published in the January 2018 issue of Tampa Bay Parenting Magazine.


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