A small waterfront town on Boca Ciega Bay with its own main street, Beach Boulevard. Hurricane Helene flooded the waterfront in September 2024. Some rooms never came back, and the ones that did have a story to tell about it.
Jesse Sapp is the pitmaster, and the name honors his late sister, Kimberley Sapp. The Tampa Bay Times reports he cooks over oak and sometimes pecan on a pit smoker more than 50 years old, at the site of the former Hogley Wogley BBQ, and quotes him: 'We take pride in how we clean our ribs.' Spare ribs, chicken, top sirloin and pork shoulder come with mustard-based sauce, hot or mild.
Gulfport's brewery turned six in June 2026 and threw its second annual Beerfest to mark it. Three of its beers medaled at the 2026 Best Florida Beer competition, and in August it released Sea Breeze, a beer honoring local newspaper history back to 1886. There is live music in the biergarten, a Tuesday run club and Thursday trivia. Since June 2026 it also opens at 9am as a breakfast cafe pouring Black Crow Coffee.
Live music some nights. Go before the band starts if you want to talk.
A Cuban restaurant on Gulfport Boulevard, up the hill from the waterfront. The Gabber's book club, which reads Florida authors, meets here at 5:30 p.m. on the second Wednesday of every month, with a schedule running through November 2026.
The building went up in 1925 and has been a bar for almost 100 years ... Walt's Place, the Swamp Club, Gulfport on the Rocks for 40 years, then Salty's, before Hurricane Eddie's moved in late in 2020. St. Pete Rising reports it held one of the first liquor licenses in Pinellas County. Helene flooded it in September 2024 and it stayed shut for 16 months, serving on the patio from St. Patrick's Day 2025 while the walls, floors, ceilings and restrooms were rebuilt. It reopened on March 12, 2026 with live music Friday to Sunday, poker, bingo, karaoke and a Thursday locals night.
Live music some nights. Go before the band starts if you want to talk.
A family-run Greek and seafood room on the corner by the Gulfport pier, open since 2011 and run by Dia and Gus Vartsakis. Helene put more than four feet of water through it in September 2024 and nearly everything had to be replaced. 'We saw our time, energy, passion, and livelihood destroyed,' Dia Vartsakis told St. Pete Rising. It reopened on August 29, 2025, in time for GeckoFest, and The Gabber's publisher called its return a marker for downtown Gulfport's recovery. Two shops that shared the building, Qi Crystal Energy and Paw Paw's Pet Boutique, did not come back.
The bar Gulfport measures storms by ... after Hurricane Helene The Gabber's publisher wrote a note titled 'The O'Maddy's Index', and during Idalia in 2023 police closed it because the corner was under water. It faces the Gulfport Pier, has live music every day and welcomes dogs at the outside tables. In March 2026 it opened a second floor, a long-planned expansion that The Gabber says came after 20 years in business.
Live music some nights. Go before the band starts if you want to talk.
Pia and Tom Goff have run this trattoria since 2005, cooking to order and baking their own cakes and desserts. The private courtyard is what people come for, and in 2021 they took over the building next door as Pia's Veranda for more seats, outdoor tables and live entertainment. They fed local seniors free during the pandemic and gave away pasta dinners in 2025 when SNAP benefits were disrupted.
Live music some nights. Go before the band starts if you want to talk.
The Matchin family's second shop, opened in Gulfport in 2023 in a former bakery space. The Gabber reported the ice cream is made in house from organic coconut milk, with 12 flavors a day and six of them rotating. The own site now lists Hershey's dairy ice cream at this shop too. With Golden Dinosaurs closed across the street since January 2025, this is the plant-based stop left on Beach Boulevard.
Named for Aunt Stella, born in Manhattan in 1910, who became a nun and loved to cook. The restaurant serves its full menu all day, breakfast included, and keeps a doggie menu for the patio.
A hurricane-themed tavern that opened on September 25, 2024 ... one day before Hurricane Helene hit Gulfport. It is three rooms in one: a main dining room, The Crow's Nest rooftop bar over Boca Ciega Bay and BARk, a dog-friendly tiki bar. Artist Derek Donnelly later painted a 'Guardian of Gulfport' mural on the building about the town getting through Helene and Milton. Live music runs Tuesday to Sunday.
Live music some nights. Go before the band starts if you want to talk.
Larisa and Tommy Lussiano opened this wood-fired pizza and sandwich pub in 2023. They told The Gabber the 2024 hurricanes devastated them and credited staff, friends, family and the town for getting them reopened quickly. St. Pete Rising listed it among the first Gulfport rooms to resume service.
