Is this going to be the biggest weekend in Tampa? This lineup blends bold tradition, big laughs, and community gatherings, and historic matches. Check out what’s happening in Tampa this 2026 Gasparilla weekend:
Bert Kreischer – Permission To PartyWhat: Comedy show featuring Tampa native Bert KreischerWhen: Friday, Jan. 30, 2026, at 7p.m.Where: Benchmark International ArenaCost: Resale tickets can be found on Ticketmaster
Bert Kreischer’s career has evolved from Rolling Stone’s infamous “Number One Partier in the Nation” to one of the top-grossing stand-up comedians in the world—and a powerhouse entrepreneur, content creator and entertainment brand. Named by Forbes as “one of the best storytellers of his generation,” Kreischer has parlayed his signature comedy and authenticity into a dynamic media empire
Seminole Hard Rock Gasparilla Pirate FestWhat: Pirate invasion, parade, and waterfront festivitiesWhen: Saturday, Jan. 31, 2026, from 11:30 a.m. to 7:30 p.m.Where: Downtown Tampa, centered around Bayshore BoulevardCost: Invasion and parade are free; brunch and stage performances are ticketed separately
The Seminole Hard Rock Gasparilla Pirate Fest is a full day of pirate celebrations, combining lively waterfront pageantry with community fun. Centered around the legendary pirate invasion of Jose Gaspar and his crew of swashbucklers, the festival features the “invasion” flotilla, a spirited Parade of Pirates along Bayshore Boulevard, and live music and entertainment on multiple stages.
After Gasparilla Cleanup 2026What: Cleanup efforts after Gasparilla paradeWhen: Sunday, Feb. 1, 2026, from 8 a.m. to 11 a.m.Where: Downtown Tampa, centered around Bayshore BoulevardCost: Free but must RSVP
The pirates have come and gone — now it’s time to reclaim our bay! 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. Help us keep our city and waterways beautiful while celebrating the spirit of community pride! All supplies will be provided and free shirts on a first come first served basis.
2026 NHL Stadium SeriesWhat: Tampa Bay Lightning vs Boston BruinsWhen: Sunday, Feb 1, 2026, at 9 p.m.Where: Raymond James Stadium
The Tampa Bay Lightning will face off against the Boston Bruins at Raymond James Stadium on February 1, 2026, in the first-ever NHL outdoor game held in a football stadium in Florida. 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 Week
Weeknights in Tampa keep the energy flowing with classic sounds, competitive thrills, and big-name comedy:
The Tommy Dorsey Orchestra: Monday, Feb. 2, 2026, at 11:30 a.m. and 1:30 p.m. (additional dates available through Friday, Feb. 6, 2026) as part of the Busch Gardens Real Music Series at Busch Gardens Tampa Bay, 10165 McKinley Drive, TampaAdam Carolla: Wednesday, Feb. 4, 2026, at 7 p.m. at Funny Bone Comedy Club & Restaurant, 1600 E. Eighth Ave. C-112, Tampa2026 Florida State Fair: Opening Thursday, Feb. 5, 2026, at 11 a.m. at Florida State Fairgrounds, 4800 U.S. Highway 301, Tampa