Whether you’re rolling into town for the famed First Friday Art Walk or a longtime local with a taste for something new, Gulfport has good eats covered. The city’s downtown and waterfront district are essentially walkable paths for restaurants, bars and coffee shops that can win over any small town food critic. 
A romantic Italian restaurant with an outdoor garden and string lights, Pia’s Trattoria  – coined Pia’s by locals – is downtown’s coziest spot for from-scratch lasagna. The menu sticks to classic Old Italy pastas and salads and offers options that are hard to find just anywhere (looking at you Salmon Di Capri.) 
Watch the waves lap at the shores of Gulfport Beach as you feast on fish tacos, sandwiches, rum cake, blackened grouper… what’s not to love as you sit and watch the world go by? With daily specials, a live music courtyard, and a delicious menu, this Gulfport gem is often crowded… but there’s always room for one more.
This one is for the vegans. Gulfport’s Golden Dinosaurs is a Beach Boulevard legend with a 100% animal-free menu and an elaborate collection of cream sodas. Plus, the veganism doesn’t end with veggie burgers. Golden Dinosaurs offers offbeat vegan bites such as their best selling Cuban, French dip and the mysterious po’ boy. It’s seriously all meat and dairy free, and seriously COVID-19 safe with a walk-up window and outdoor dining. 
Get your coffee and muffin or tea and sandwich or donut and iced latte or… well, you get the idea: whatever morning or midday nosh you crave, this coffee house delivers. Avo toast and lavender latte? Monte Cristo and chai? Yeah, they’ve got that. Plus, the retro Florida decor, shady courtyard, and friendly rep the place has will have you coming back for more.
A coffee lounge reincarnated from the 1970s, SumitrA Espresso Lounge is one conversation pit away from going barefoot only. The shop sells solid Americanos and chai lattes alongside handmade pastries and crafted cocktails. The menu is extensive and the baristas are coffee connoisseurs that don’t have time for the nonsense of chain coffee stores. Much of what they serve is as gluten free, CBD infused… it is Gulfport after all. 
Steps across from the Historic Peninsula Inn, shaded by tropical greenery, Gulfport Brewery serves up frothy, tasty, beer – but that’s not all that keeps the locals coming back. They serve Gulfport faves like Gulfport Grilled Cheese, the Californication, and – of course – a might Cuban Sammy. 
Habana Café is Gulfport’s favorite Cuban kitchen. The inside of the old-style restaurant’s walls are completely covered in local mural work and the menu is full of traditional Spanish cooking. They serve the famous Arroz con Pollo a la Chorrera (only on Fridays) black bean soup and according to Habana Cafe itself, «the best flan you’ve ever had.»
Looking for classic Italian-American fare? Look no farther than Tutto Bene, serving up pizzas, pastas, and frutti di mare. As with so many Gulfport restaurants, they offer indoor dining but also have an ample, dog-friendly, spacious courtyard for diners. This Italian bistro also boasts luscious made-from-scratch desserts and some lovely wines.
Catch Backfin Blue while you can – this downtown Gulfport seafood spot is only open on Friday, Saturday and Sunday nights. The little red house is known for serving up fresh jumbo crab legs and a buttery seafood bake for those three special nights a week, outside only. The demand for blue is on, says Backfin, as the restaurant offers call aheads and only takes walk-ins when there is a rare availability. 
Gulfport’s Historic Peninsula Inn towers over most of the village as a yellow icon, and the hotel’s front porch restaurant, Isabelle’s Restaurant in Gulfport doesn’t disappoint. The warmly lit outdoor seating area serves southern cooking with a coastal Floridian twist. Seafood linguine is next to old fashioned pork chops which is next to a vegan vegetable stir fry. Catch the drift?
If you’re in town for the night or weighed down with peach scotch and surf & turf, the Historic Peninsula Inn offers homey rooms in the heart of Gulfport, breakfast in bed included.