The Brief Due to expected windy conditions, the Gasparilla pirates decided to shorten their flotilla route, similar to what they did in 2022. The Hillsborough County Sheriff’s Office will keep a close eye on the water thanks to the help of 77 boats from 40 agencies. Due to expected windy conditions, the Gasparilla pirates decided to shorten their flotilla route this year. READ: Gasparilla 2026 Guide: Here’s what you need to knowThe flotilla route was shortened like this back in 2022 due to the weather. Dig deeper:The Hillsborough County Sheriff’s Office will be watching the water closely on Saturday.