Dine Outdoors in Gulfport

Don’t let the name fool you - the menu here leans more all-American than Irish pub. To find this popular spot, look for the colorful umbrellas and large patio across from the Gulfport Beach and pier. It’s a fun, Key West-style atmosphere, but family-friendly, too (there’s a kids’ menu). Try This: Order the Mahi Tacos with baja slaw or the “Windy Cindy” a grilled cheese sandwich with bacon, turkey, tomato, havarti cheese and chipotle mayo on marble rye.

Couldn’t everyone use a little romance? Or a relaxed dinner out with friends? This charming “Old World” restaurant in tiny Gulfport makes it possible with simple, fresh Italian cuisine and a never-rushed attitude. Recently named #1 foodie hotspot in the area in the 2025 Best of St. Pete-Clearwater awards, this place is popular - consider making a reservation. Enjoy dining al fresco with two outdoor dining options: sidewalk dining out front or a covered patio out back. Try This: The Penne Quattro Formaggi al Forno (translation: penne pasta in a cream sauce with four cheeses) is divine. Choose an Italian wine to accompany your meal.

Fairy lights, towering palms, lush plantings and live music create a magical scene at Pia’s Veranda, the al fresco space next to Pia’s Trattoria. Thanks to fans and heaters, the veranda always stays comfortable for outdoor dining. Live music from a small covered stage adds to the vibe. Called “intimate” and “adorable” by guests, Pia’s gets the food right, too. Think casual Italian fare, a medley of comfort foods and inventive small plates that encourage sampling. Lasagna (served in a cast-iron skillet) and house-made tiramisu are among the favorite dishes. Pia’s Veranda is open for walk-ins only, Wed.-Sun.

Florida insiders know that some of the best dining venues are tucked inside very basic strip malls—like this Mediterranean spot with Moroccan flair. Early-bird specials are very popular at this fine dining outpost, but the candle-lit outdoor tables (on a covered patio) are most romantic after dark. The Pearl offers game choices not widely found in these parts, including camel. Order one of their delicious tagines, a trip to Morocco for your palate. And who can resist an ahi tuna ‘martini’? Don’t even try.

Digging into an ooey, gooey crepe with sparkly views of Boca Ciega Bay—what a great way to start the day! Located at the Sea Breeze Manor Inn on Gulfport Beach, this little breakfast and lunch spot specializes in sweet and savory crepes. The savory ones are French-style galettes, make with buckwheat flour. Frank’s French toast always hits the spot, soaked in a secret-recipe batter, and topped with fruits, granola, powdered sugar and whipped cream. If you’re of the carb-free persuasion, try the shakshuka.

Fitting in perfectly with quirky, colorful Gulfport, Stella’s is a woman-owned, dog-friendly diner with outdoor seating under lime green umbrellas in the Village Courtyard. As befits a diner, they offer an award-winning breakfast (try the corned beef hash), but it’s worth stopping by later in the day for a smash burger or a fried green tomato sandwich drizzled with chipotle sauce. Really hungry? That meatloaf tower (with stacked mashed potatoes, fried green tomatoes, bacon and gravy) has your name written all over it. Afternoon happy hours and live music add to the festive vibe.

Gulfport Brewery + Eatery has a beautiful courtyard to sip beer from the "Best New Brewery" in Pinellas County (as voted in Creative Loafing's Best of the Bay). While beer might be in the spotlight of this establishment, don't forget to try some delicious munchies, such as their assortment of flatbreads and hotdogs. 

Gluten-free pizza isn’t an afterthought at Tommy’s Hideaway, an independent pizzeria and pub. Of their 15 crispy-crust wood-fired pizzas, you can get any of them with a cauliflower crust, including their swoon-worthy hot and cold burrata pies. That’s just one of the things to love about this downtown Gulfport joint (a ‘Best of the Bay’ winner for Italian food.) They’ve got outdoor seating out front, plus a side patio and a walk-up bar (beer and wine only) with 12 seats, all the better to enjoy a sultry evening or totally chill afternoon. Be sure to order some garlic-parmesan fries for the table.

Take in some of Gulfport’s finest views from the Crow’s Nest, the patio bar perched on the second floor of Stormrunners. Open-air tables and banquette seating reveal elevated views of Boca Ciega Bays and sherbet-hued sunsets. There’s also a downstairs indoor dining room here, and a tiki bar where dogs are welcome. The full menu is available throughout, featuring fun cocktails and popular handhelds like a New England-style lobster roll and a grouper BLT, served blackened or grilled. Your choice, but when in Gulfport, go for the grouper!

Good burgers and good pizza? Few eateries can nail them both. That’s what makes Siri’s (named after the daughter of the owners) such a fun discovery. Burgers are made with their own grind of meat from three cuts of steak, their fries are hand-cut, and rolls are made in-house. The New York-style pizzas are hand-tossed using their own dough. There’s outdoor seating for 20 people, on metal tables with umbrellas for shade.