O’Maddy’s Bar & Grille
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. Even better, you have two outdoor dining options: sidewalk dining out front or a covered back patio. This place is popular - consider making a reservation. 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.
Neptune Grill is a family-owned restaurant with authentic Greek and Mediterranean dishes including Saganaki, Gyro off the spit, Spanakopita and more. Sip on traditional Greek Wins and enjoy live music Thursday through Sunday each week.
Caddy's has multiple locations in St. Pete/Clearwater, and all of them offer great views and tasty bites, so it's hard to pick a favorite, but it's also hard to beat the Gulfport location. Enjoy views of downtown Gulfport and Boca Ciega Bay as you sip on frozen cocktails.
Gulfport Brewery + Eatery
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.