Is this going to be the biggest weekend in Tampa? Check out what's happening in Tampa this 2026 Gasparilla weekend:Bert Kreischer – Permission To PartyWhat: Comedy show featuring Tampa native Bert KreischerComedy show featuring Tampa native Bert Kreischer When: Friday, Jan. 30, 2026, at 7p.m. Join Keep Tampa Bay Beautiful for our annual After Gasparilla Cleanup as we come together to clear litter and debris left behind after the festivities. Part of the 2026 Navy Federal Credit Union NHL Stadium Series™, the matchup caps off a month-long celebration of hockey in the Sunshine State. More To Explore This WeekWeeknights in Tampa keep the energy flowing with classic sounds, competitive thrills, and big-name comedy: