Comedians Bert Kreischer and Tom Segura are rolling into downtown Tampa this week to sign bottles of their Por Osos Vodka, with a Thursday afternoon stop at a 1946 dive bar and a Friday morning appearance inside MacDill Air Force Base. The pair, both stars of the hit podcast 2 Bears, 1 Cave, will be at The Hub's package store at 1 p.m. Thursday before heading to the MacDill Exchange at 11 a.m. Friday. It is a homecoming of sorts for Kreischer, a Tampa native, and a return to a state Segura also once called home.
The Tampa stop was first reported by Creative Loafing Tampa, which detailed the pair's itinerary at The Hub, located at 719 N Franklin St. The Hub bills itself as a bar, pub, and music venue, and the outlet notes that Kreischer, 53, and Segura, 47, will both sign Por Osos Vodka bottles for fans there. Kreischer is scheduled to sign bottles at liquor stores across the Bay Area as part of the broader promotional swing, according to the same report.
The Hub itself carries decades of downtown Tampa history. The building at 719 N Franklin St. first opened in 1946 under Pio Guerra Jr. and expanded into a piano cocktail lounge in 1949, once serving judges, lawyers, and boxing champions before settling into its current identity as a cash-only dive bar, according to Locations Hub. The bar celebrated its 60th anniversary in downtown Tampa back in 2006. Unlike many nightlife spots downtown, The Hub also runs an attached package store, per the Scoundrel's Field Guide, which allows it to legally sell sealed bottles for off-site consumption alongside its regular tavern service — the exact setup that makes a retail bottle-signing possible at the location.
A Florida State Legend Behind the Bar Tour
Kreischer's ties to Florida run deep and predate his current fame. He graduated from Jesuit High School in 1991, per the CL Tampa report, before his Florida State University years cemented his reputation as a legendary partyer. An April 1997 Rolling Stone profile titled “Bert Kreischer: The Undergraduate” crowned him the top partyer at FSU during his sixth year of college, according to Wikipedia. That article is credited as the original inspiration for the 2002 film Van Wilder, and CL Tampa notes Kreischer is considered an inspiration for Ryan Reynolds' title character.
Segura also has genuine Florida roots, having graduated from Saint Edward's School in Vero Beach before building his stand-up career and co-founding YMH Studios with his wife, Christina Pazsitzky, according to Wikipedia. His late father was reportedly a prominent community leader and hospital board chairman in Vero Beach, per Vero News. The duo's chemistry now fuels 2 Bears, 1 Cave, which attracts more than 500,000 monthly listeners and regularly places among the top comedy podcasts in the country, according to Muck Rack.
A Sobriety Detour Before the Vodka Push
The bottle tour arrives amid a personal wrinkle for Kreischer: he tried the dry life after going on blood thinners, per CL Tampa, and has promised to return to drinking alcohol in the fall of 2026. Por Osos Vodka itself is named for the podcast that made the duo famous, and it launched in February 2024 as a partnership between Kreischer, Segura, CPG venture studio Drip MFG, and Mexcor Distribution, according to a release carried by PR Newswire. The vodka uses non-GMO wheat and Persedo C.R.A.F.T. technology, positioning it as an accessible, mid-market gluten-free spirit.
Friday's Stop Targets MacDill's Military Community
After Thursday's downtown signing, Kreischer and Segura will appear inside the MacDill Exchange at 11 a.m. Friday, per Por Osos Vodka's own schedule as relayed by CL Tampa. The Main Exchange operates inside Building 926 at 3108 N Boundary Blvd and serves a base community of nearly 17,000 service members, family members, and civilians daily, according to The Exchange Post. MacDill Air Force Base is also home to U.S. Central Command and U.S. Special Operations Command, giving the Friday stop a very different audience than Thursday's downtown crowd.
The Tampa visit isn't Kreischer's first brush with local goodwill. He organized “BERT AID” at Clearwater's Ruth Eckerd Hall in October 2024 to raise relief funds for Hurricane Helene victims, with proceeds directed to Metropolitan Ministries, as previously reported by Hoodline. Both comedians have also kept busy well beyond Tampa Bay: Kreischer headlined the “Laughing on the Lake” outdoor comedy festival at Ozarks Amphitheater in Camdenton, Missouri, in May 2026, a bill that included comics like Kathleen Madigan and Rory Scovel. Segura, meanwhile, has branched into hospitality as a co-owner of Ciccio Bomba, an Italian bakery and restaurant concept planned for Austin, Texas.
