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:<\/p>\n
Bert Kreischer \u2013 Permission To PartyWhat:\u00a0Comedy show featuring Tampa native Bert KreischerWhen:\u00a0Friday, Jan. 30, 2026, at 7p.m.Where:\u00a0Benchmark International ArenaCost:\u00a0Resale tickets can be found on Ticketmaster<\/p>\n
Bert Kreischer<\/a>\u2019s career has evolved from Rolling Stone\u2019s infamous \u201cNumber One Partier in the Nation\u201d to one of the top-grossing stand-up comedians in the world\u2014and a powerhouse entrepreneur, content creator and entertainment brand. Named by\u00a0Forbes\u00a0as \u201cone of the best storytellers of his generation,\u201d Kreischer has parlayed his signature comedy and authenticity into a dynamic media empire<\/p>\n Seminole Hard Rock Gasparilla Pirate FestWhat:\u00a0Pirate invasion, parade, and waterfront festivitiesWhen:\u00a0Saturday, Jan. 31, 2026, from 11:30 a.m. to 7:30 p.m.Where:\u00a0Downtown Tampa, centered around Bayshore BoulevardCost:\u00a0Invasion and parade are free; brunch and stage performances are ticketed separately<\/p>\n The\u00a0Seminole Hard Rock Gasparilla Pirate Fest<\/a>\u00a0is 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 \u201cinvasion\u201d flotilla, a spirited Parade of Pirates along Bayshore Boulevard, and live music and entertainment on multiple stages.<\/p>\n After Gasparilla Cleanup 2026What:\u00a0Cleanup efforts after Gasparilla paradeWhen:\u00a0Sunday, Feb. 1, 2026, from 8 a.m. to 11 a.m.Where:\u00a0Downtown Tampa, centered around Bayshore BoulevardCost:\u00a0Free but must RSVP<\/a><\/p>\n The pirates have come and gone \u2014 now it\u2019s 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.<\/p>\n 2026 NHL Stadium SeriesWhat:\u00a0Tampa Bay Lightning vs Boston BruinsWhen:\u00a0Sunday, Feb 1, 2026, at 9 p.m.Where:\u00a0Raymond James Stadium<\/p>\n 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\u2122, the matchup caps off a month-long celebration of hockey in the Sunshine State.<\/p>\n More To Explore This Week<\/p>\n Weeknights in Tampa keep the energy flowing with classic sounds, competitive thrills, and big-name comedy:<\/p>\n The Tommy Dorsey Orchestra:\u00a0Monday, 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\u00a0Busch Gardens Real Music Series<\/a>\u00a0at Busch Gardens Tampa Bay, 10165 McKinley Drive, TampaAdam Carolla<\/a>:\u00a0Wednesday, Feb. 4, 2026, at 7 p.m. at Funny Bone Comedy Club & Restaurant, 1600 E. Eighth Ave. C-112, Tampa2026 Florida State Fair<\/a>:\u00a0Opening Thursday, Feb. 5, 2026, at 11 a.m. at Florida State Fairgrounds, 4800 U.S. Highway 301, Tampa<\/p>\n","protected":false},"excerpt":{"rendered":"Is this going to be the biggest weekend in Tampa? This lineup blends bold tradition, big laughs, and…\n","protected":false},"author":2,"featured_media":136003,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[10],"tags":[684,135,137,136],"class_list":{"0":"post-136002","1":"post","2":"type-post","3":"status-publish","4":"format-standard","5":"has-post-thumbnail","7":"category-tampa","8":"tag-events","9":"tag-tampa","10":"tag-tampa-headlines","11":"tag-tampa-news"},"_links":{"self":[{"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/posts\/136002","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/comments?post=136002"}],"version-history":[{"count":0,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/posts\/136002\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/media\/136003"}],"wp:attachment":[{"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/media?parent=136002"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/categories?post=136002"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/tags?post=136002"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}