Get ready for some real old-school Florida! Gulfport, a hidden gem, is situated on Boca Ciega Bay, a southwest suburb of St. Petersburg. The town dates back to 1867, when Civil War veteran James Barnett and his wife, Rebecca, settled in the area with their family. In the early 1880s, Hamilton Disston purchased the land and renamed it Disston City, with hopes that the railway would pass through—but the railroad was only built to St. Petersburg. In the next six years, the name of the city changed several times until in 1910 it finally became Gulfport.
Idyllic Gulfport is lined with historical brick streets and shaded by large oak and palm trees. Hop aboard the Gulfport Waterfront Trolley for a tour around town, and explore the numerous shops and restaurants. The trolley is offered on Fridays and Saturdays and is free to the public. Stroll down Beach Boulevard and check out the Beach Bazaar for its nautical-theme collectibles and Bo-Tiki for ladies must-have beachwear, or stop in one of the many studios such as Owen Pach Glass & Sculpture, Tropical Funk, and Domain Home Accessories & Gallery.
Don’t miss Gulfport Fresh Market on Tuesdays, where an assortment of vendors sell fresh-caught fish, baked goods, cheese, spices, and locally grown honey, along with a variety of artisan knick-knacks. For foodies, there’s a large selection of dining options in town, such as Isabelle’s Southern Cuisine, Backfin Blue Cafe, and Pia’s Trattoria.
In the mood for some dancing? The Gulfport Casino, built in 1935, hosts daily swing, salsa, tango and ballroom dance classes. Adjacent to the casino is Gulfport Beach, an ideal place to unwind after a long day. The beach offers ample parking, bocce courts, a large playground, and a beach volleyball court. A popular stop for adamant fishermen is Williams Pier, which was built in 1906 and extends more than 500 feet into the Boca Ciega Bay.
Year-round, during the Gulfport Art Walk on First Fridays and Third Saturdays, Beach Boulevard is lined with local vendors, independent artists, and musicians. And don’t miss GeckoFest on Labor Day weekend or the Tangerine Blues Fest in September.
Where to Dock
- Gulfport Municipal Marina (727-893-1071, mygulfport.us) Located in a protected basin along the ICW, the marina offers 250 slips, a ship store with bait and tackle, pump-out services, and gasoline and diesel fuel.
Where to Dine
- Stella’s (3119 Beach Blvd. S, 727-498-8950) A great waterfront spot for breakfast or brunch. Local favorites include the Texas-style french toast and the house-made corned beef hash.
- O’Maddy’s Bar & Grille (5405 Shore Blvd S., 727-323-8643) Set on the water with outdoor setting, theyoffer happy-hour specials from 8 a.m. until 8 p.m. and karaoke.
- Peg’s Cantina (3038 Beach Blvd., 727-328-2720) Some of the best Mexican dishes around. Favorites include the crab quesadilla, and there are craft beers from Cycle Brewing.