There are excellent choices right in Gulfport. In 2011, Gulfport was a “Best for Food” finalist in the Rand McNally/USA Today “Best of the Road” contest. Most restaurants are on Beach, Shore, Gulfport Blvd or 49th St S.
Backfin Blue - Outstanding “Old Florida” fare in an old house, right on Beach Blvd. Famous for their crab cakes. Casual, ladi-back setting. 727-343-2583. 2913 Beach Blvd. in the Historic Waterfront District.
O’Maddy’s Bar & Grill - Always a crowd and a favorite for both location and food. O’Maddy’s is right on the water, with ample outside seating. Watch the game, watch the dolphins, watch the people. Tried the burgers or fish entrees. The place to be any time of day. 727-323-8643. Shore & 54th St S. in the Historic Waterfront District.
Habana Cafe - Located outside the central dining and entertainment district, Habana is known bay-wide for it’s excellent Cuban cuisine. Consistently voted “Best of the Bay”. 727-321-8855. 5402 Gulfport Glvd. (22nd Ave S at 54th St S.)
Island Flavors & ‘Tings - Authentic Jamaican Cuisine. Mouthwatering. Restaurant, catering and grocery store. 1411 49th St S. in South 49th District.
Mid-Peninsula Seafood - Looking for great fresh seafood takeout or planning to do a little cooking of your own? Mid-Peninsula is the place! Buy fresh whiting, sea bass, salmon, snapper, oysters, shrimp and crab. Try the hush puppies! Closed Sundays. 400 49th St S, St Pete. 727-327-8309.
Pia’s Trattoria - Pia’s has expanded over the last few years and that is great news for you! Lovely indoor seating as well as the best tropical patio in town. Italian dining at its best. ia’s is open for breakfast on weekends. 727-327-2190. 3054 Beach Blvd S.
Peg’s Cantina & Brew Pub - fresh brewed beer and fresh Mexican. Terrific patio, deck and indoor seating options for whatever weather we’re experiencing. Dinner nightly; lunch on weekends. Closed Mondays. 727-3282720. 3038 Beach Blvd. in the Historic Waterfront District.
Smokin’ J’s BBQ - What can I say? We’re from Texas, so we know Real Texas BBQ. And this is it. And then some. All I can say is, order way more than you can eat and take it home. You’ll thank yourself the next day. 727-329-8624. 5145 Gulfport Blvd. Closed Mondays.
Stella’s Deli & Gelato - So far all we’ve had is the scrumptious breakfasts but if the other deli items and the gelato are half as good as breakfast, we’re in! 727-498-8950. 3119 Beach Blvd in the Historic Waterfront District. If a menu item is marked as one of their specialties, get it. Or get all of them - bring friends!
T & Me Tea Company - breakfast and lunch. Excellent breakfast & coffees, plus...wait for it...tea! This family-run business loves, loves, love tea. 727-331-5253. 2908 1 Beach Blvd in the Art Village Courtyard.
Mangia Gourmet - One of the area's newer restaurants but with a great deal of buzz. For some people, healthy eating is a mission. Owner and chef Jill Johnson won People's Choice cateogry in the Top Local Chef competition in 2015. Check our the new Sunday Brunch and the amazing Sangria. Tasty, homemade, local and environmentally friendly foods including Vegan, Gluten Free, Vegetarian and Organic. You'll be able to taste it!
Little Tommie's Tiki - Little Tommie's seems to be the charm for the waterfront dining location that had been plagued with a fair amount of restaurant turnover. Offering something Gulfport had been missing, try the rotating beer offerings and bold flavors this establishment has to offer.
Neptune's - has something for everyone. Comfortable inside with mouth-watering dishes, plus a lively waterfront bar with live music outside. Not to be missed.
Siri's Gourmet Burgers & Pizza - another of the new entrants on the dining scene, Siri's stole our hearts one night after a late flight left us with few dining options open. But it's the burgers and FABULOUS french fries that keep us coming back. Creative combos as well as your basic burger.
Tangelo's - My first experience with Tangelo's was the chocolate-crusted key lime pie. The only problem with it was that after trying it I wanted the entire pie. (Which you can buy, btw.) But later dining proved they were more than a one-pie-slice show and we keep coming back. Breakfast is available on weekends too, and it's right next to Stella's in case the wait there is too much for you!
Yummy’s - a casual lunch and dinner spot. Best Chicago-style hot dog in the area and, again for those in-the-know, they also sell Blue Bell ice cream. Happy cows from Brenham, Texas simply make better ice cream. Before it was available in Florida, people were know to bring it in themselves! 727-321-YUMY. 2914 Beach Blvd S, in the Art Village Courtyard.
Anytime Pizza - in the Historic Waterfront District on Beach Blvd S. New York style pizza, fantastic sandwiches and fresh salads.
Gulfport Cafe - an excellent choice for breakfast and one of the best deals in town. Townshores off 58th St S. Checkout Facebook for a menu. (Note August 2015: Gulfport Cafe has been sold and is undergoing renovations at this time. Still open for business during renovations. Fingers crossed our favorite breakfasts and waitstaff are preserved!!!)
Isabelles - Let’s put it this way: St. Louis Ribs with Mac & Cheese, Pecan Encrusted Grouper with Creamed Spinach & Asparagus, Lobster Bisque, Gumbo, Cornbread, Key Lime Pie, Chocolate Chess Torte...yup, even if you just finished eating we just made you hungry all over again. Located inside The Peninsula Inn & Spa on Beach Blvd S in the Historic Waterfront District.
McDonald’s. You know it. 5111 Gulfport Blvd. Drive-thru and playground.
Several don’t-miss favorites.
The Hurricane - Not just for hurricane-watching, the Hurricane has some of the best crab cakes in the area, along with grouper and fish spread. 727-360-9558, 807 Gulf Way,
Paradise Sweets - Gourmet candies, coffees, home-town Working Cow ice cream and water views make this a perfect way to begin or end your trip to Pass-A-Grille. On Historic 8th Ave at the water’s edge (Gulf Way).
Brass Monkey - sandwiches, soups, salads and entrees. Try dining on the patio upstairs. Watch for gulls - they will try to steal your sandwich! The owners hail from the restaurant industry in the Chesapeake Bay area, so they know crab cakes! “All killer! No filler!” 727-367-7620. 709 Gulf Way, Suite 200,
Black Palm Restaurant - A wonderful melding of Caribbean and So American cuisines. Reservations recommended. 727360-5000. 109 8th Ave, Pass-A-Grille.
The Don Cesear Hotel Sunday Brunch - Yes it’s expensive. But the food is superb, the views are out-of this world and you won’t need to eat again until the next day. Over 200 culinary delights. Not a typo! 200. Ocean views on three sides of the dining area. Reservations recommended. Located in the Lowes Don Cesar Hotel on St Pete Beach, Gulf Blvd. at Pinellas Bayway.
Bern’s Steakhouse & Sidebern’s - Legendary. Reported to have the largest selection of wines in the world and a 24 page dessert menu. Often called the most unusual steakhouse in the world. 813-251-2421. 1208 Howard Ave, Tampa. Sidebern’s is next door
St Pete Restaurants
St Pete has several “don’t miss” restaurants as well.
Red Mesa Restaurant (not Cantina) - Regional Mexican and southwestern flavors. My personal favorite. If you’re headed to a cultural evening event downtown, Red Mesa has a special “Sunset” menu before 6 pm guaranteed to get you out and on your way. But linger if you have time, and try out many of the wonderful appetizers (like Chorizo Fundido so delicious you may be ruined for life), the entrees (my favorite Palomilla Steak) and desserts (Coconut Natilla for coconut and chocolate lovers). 727-527-8728. 4912 4th St N, St Pete.
Central Avenue Oyster Bar - Fresh seafood, steaks, chicken and pasta dishes. Try it with a movie at Muvico at Baywalk. 727894-9728. 249 Central Ave, downtown St Pete.
Gratzzi - Northern Italian cuisine downtown. 727-623-9037. 211 2nd Ave N., St Pete. (Formerly located in the Baywalk complex.)
Skyway Jack’s – A St Petersburg institution. 2795 34th St S, St Petersburg. Billed as one of the oldest, strangest, coolest, bestest places for breakfast. Serving for over a quarter of a century. 727-867-1907
Madeira Beach Dining
Scully’s - Dine waterside and watch the jet-skier’s from the boardwalk. Great location, but come for the food. Be prepared to take a doggie bag home and leave room for the Key Lime Pie. 727. 393-7749. 190 John’s Pass Boardwalk, Madeira Beach.