Few towns in Florida are able to marry that rickety-yet-romantic Old Florida feel with a truly offbeat, artsy aesthetic in the way that Gulfport does. This eclectic jewel of a town is nestled right on the shores of the Gulf of Mexico’s Boca Ciega Bay. At once colorful, vibrant and naturally easygoing, Gulfport welcomes artists, musicians, lovers of gourmet food, craft beer aficionados, karaoke buffs and more.
Arts & Culture
For eclectic local art, head to Art Village Courtyard. You'll find everything from glass blowing exhibits to local arts and crafts. If you want to grab a cup of coffee or a craft beer and sit in the shade, this is the place. You can also stroll into surrounding boutiques to see the intriguing wares of local artisans.
Semi-monthly Gulfport Art Walks celebrate the town's No. 1 attraction: art. You won’t just find Gulf beach sunset paintings here, either. Think abstract wall décor and jewelry made from turquoise and shells.
Start with a stroll down Beach Boulevard. Looking for an Elvis Coaster? A brass mermaid? A quirky gift card? A hula girl lamp? Chances are you’ll find most, if not all, of these among the many quirky boutiques that line this strip.
On Tuesdays from 9 am to 3 pm, browse Gulfport’s popular Fresh Market. You’ll find locally caught fish, produce (local and organic), freshly baked breads, cheese, nuts and granola, herbs, plants and flowers, home-made dog treats, hand-made soaps and body care products, candles, jewelry and local art and crafts. Live music adds to the festive atmosphere.
Dining & Nightlife
The quaint village of Gulfport doesn’t skimp on its dining options – in fact, you’ll likely be surprised by the variety of inspired fare. La Cote Basque Winehouse is known for its classic French fare. Peg's Cantina offers some excellent Mexican food, including many veggie-friendly dishes, and it brews its own craft beer made on sight. Get your seafood fix at Backfin Blue Cafe.
Shore Boulevard is lined with enough places to constitute a night out. The crown jewel of these is O'Maddy's Bar and Grille, which hosts karaoke nearly every night. Meanwhile, the Gulfport Casino (though deceptively named) is home to swing and salsa dance events. Beach Boulevard has some fine drinking establishments as well.
Boaters should head for the basic-yet-charming Gulfport Municipal Marina, which is convenient to both inland and Gulf waters. Fuel up here while chatting with the locals about Gulfport’s interesting history and their area favorites.
Events & Festivals
Every Labor Day weekend, GeckoFest takes over the whole town, sending off summer in style. Think wacky costumes (many with a lizard theme), food vendors, a massive stage featuring local bands and a parade, all making for some fabulous people-watching (or dress up and join in the fun). In the winter, Gulfport's Get Rescued is a massive street festival that highlights local pet rescues. Every event that takes place is carried off in style, attracting locals and visitors alike.
To get your bearings in this eclectic town, take a free half-hour tour on the Gulfport Trolley, or you can check the place out for yourself on foot. Gulfport is just a short distance away from St. Pete Beach and downtown St. Petersburg, and it’s convenient to major roadways such as I-275, the Pinellas Bayway and Gulf Boulevard.