Gasparilla Pirate Festival 2023 is 8 days away, on January 28th. Mark this day in your calendars for a weekend filled with fun and excitement. From 2pm to 6pm on this day, the pirate parade will start. Watch the captains and their Krewe's float by with Pirate themed ships. Bay to Bay and Bayshore Blvd. The parade goes down Bayshore Boulevard, to Brorein Street., then goes north on Ashley Drive. The parade will end at Cass Street and Ashley Drive. This event is free for everyone.