2026 Update To Our 4-Day Dining Guide to Gulfport
After 2020 (previously known as the year-that-shall-not-be-named, we had another one in 2024. The year of Debbie-Helene-Milton. May they RIP somewhere far, far away. Many restaurants were hit hard, along with homes and businesses. We lost the Tiki bar on Shore, Let it Be Ice Cream was closed for what seemed like eternity, the brand new Stormrunners Tavern flooded the day after it opened. But troopers like Tommy’s Hideaway and O’Maddy’s were re-opened in a matter of days, providing some sense of normalcy, even if in a somewhat subdued and somber atmosphere.
We expanded our dining guide to 4 days from 3 after 2020 because the average length of stay had increased. It’s sort of returned back to normal, which means if you’re just in town for a weekend or even a long weekend, you’ll have to choose from the restaurants listed below. So sorry for you!
With a smorgasbord of notable and delicious restaurants in Gulfport, you’ll never be able to try them all—unless you spend your whole vacation eating. We wouldn’t judge you if you did, of course, but you’d be missing out on some quality beach time.
That’s why we (Beth and Terry of Splashy Ventures) have crafted this new, four-day dining guide, featuring the can’t-miss restaurants you have to squeeze in.
Sampling our complete list of recommended restaurants would take a full week of dining out for all three meals. So we made it bite-sized—perfect for those just visiting for an extra-long weekend or other short trip. Dine your way through our pretty little town in four days!
Note: Restaurants and businesses in Gulfport have been opening up since May of 2020 when the state began relaxing stay at home orders. Initially many were open only for pick up or outdoor dining, but that should no longer be there case. Nevertheless, you may want to Google the business and check opening hours to confirm. Also, almost all places suggested for dinner are also open for lunch on the weekends.
Bon Appetit!
Day 1
Dinner – Siri’s Gourmet Burgers & Pizza
We put Siri’s on this list for a simple reason: the food is excellent. And we put it under dinner for your first night because it’s perfect for late arrivals, when you just want to eat something delicious ASAP. Everything at the airport will be closed (especially these days), and you certainly don’t want your first stop in Gulfport to be the Golden Arches.
Luckily, Siri’s is open until midnight every night except Sundays, when they close at 8 p.m.
The pizza and burgers are both phenomenal. We usually order Byron’s burger (double burger with double cheese, bacon, grilled onions and mushrooms, and mayo), a meat lover’s pizza with added pineapple, and fresh cut fries.
Or call ahead for takeout to enjoy back at your vacation rental. In the summertime, you may want to plan to dine outside or get it to-go—it can get toasty in there with all those pizzas and buns baking.
Day 2 Stellas’s Gulfport
Day 2 Lunch – O’Maddy’s
Day 2 Dinner – Pia’s Trattoria
Day 2 Dinner – Pia’s Trattoria
Day 2
Breakfast – Stella’s
The breakfast here is award-winning. No, really—Stella’s won Best of the Bay in 2016 and cinched the number three position on USA Today’s 10 Best Spots for Breakfast in St Petersburg.
You can get a traditional breakfast here, but we suggest you try the Housemade Corned Beef hash and the Southern Shrimp and Grits (let’s hear it for the dining companions again). Any day that starts out with these two is already off to a great start.
Dine outside if the weather is nice and people watch—a Gulfport tradition you’ll be sure to adopt during your stay.
Also, if you’ve been to Stella’s in years past you should know that they moved up the street to the Art Village Courtyard in 2020. More space inside and out.
Lunch – O’Maddy’s
Though we recommended it for lunch, O’Maddy’s is a safe bet any time of the day. They’re also open really late (3 a.m. for you night owls) so you might find yourself coming back later on.
O’Maddy’s is also one of the few places where we switch up our orders. We almost always get Sal’s Fresh Smoked Fish Spread, but that’s because fish spread is a rite of passage when you visit Florida—we order it every time we see it on a menu. Like crab cakes and key lime pie, it’s fun (and delicious) to sample the specialties of each restaurant.
If you’re in the mood for a burger, or you didn’t get one at Siri’s, O’Maddy’s are definitely worth trying. We’re fans of Donna’s Tomato Jam and Gorgonzola Burger as well as The Weiser Hammer.
If grouper is in season, try it blackened in a main or in Suzanna’s Grouper Sandwich (a Gulfport favorite, too).
Since you’re on holiday, try a Bahama mama or rum runner for a little Florida flair. Or if you just want a snack, order the Smoked Gouda Mashed Potatoes.
Dinner – Pia’s Trattoria
Even if food wasn’t so tasty, we might still send you to Pia’s, just for the atmosphere.
While most Gulfport restaurants are decidedly low-key, recalling a bygone era, the indoor and outdoor dining areas at Pia’s may just transport you to another continent entirely. We’ve watched Pia’s transform over the years from a small dine-in restaurant to the spacious, relaxed, and refined experience it is today. Perfect for a dinner that feels like a treat.
If the weather is nice, dining outside is simply a must. We start with the Rustic Ciabatta, carbs and all. If you want butter, or more Pesto Oil Dip, just ask. The bruschetta is can’t-stop good, so be sure to pace yourself and save room for the rest of the meal.
There’s always a soup offering and it’s always worth it. Even if you’ve never dreamed of two of the soup’s ingredients blended together, trust us, you’ll love it. And If a salad is in your plans, order the Insalata Pia.
Now for the best stuff. If you eat pasta, you should get the lasagna. Period. If not, we often alternate between the Chicken Marsala and Chicken Piccata. Both come with pasta as a side dish, but you can ask for some asparagus, sautéed spinach, or sautéed vegetables instead.
In 2020 Pia’s expanded their outdoor dining area to a really spiffy sidewalk option. They had sidewalk dining before, but now there are large umbrellas, string lights and planters that block the cars parked on the street. It’s a great spot for people-watching too. In addition to the sidewalk dining, there is a very large outdoor patio/courtyard and two indoor dining areas as well – the bar and the main dining hall.
Best-Ever Chicken Salad Sandwich at Neptune
Habana Cafe’s Picadillo – is worth calling ahead for
The Crumb Factory – Croissants Croissants Croissants!
Day 3
Breakfast – Annex Coffee or The Crumb Factory
Annex is more than a coffee shop, with seasonal sandwich specials like the turkey and cranberry sandwich in the fall, but my favorite is the bacon, egg and cheese croissant. Try it with an iced latte.
Annex is more drive through and pick up place, rather than a restaurant. If you’d like another restaurant option, try the Crumb Factory on Central, just east of 58th St S.
Lunch – Neptune Grill
Since it’s a new day, it’s time for more lunchtime Bahama Mamas—and Neptune’s makes the best in Gulfport. Probably the best we’ve had since visiting Bahamas 30 years ago, in fact.
Though…Scully’s Johns Pass does a great job, too. Perhaps you’ll want to conduct a side-by-side taste test?
Anyway, back to the food. Ordering at Neptune is difficult because the menu is quite varied and everything—and we mean everything—is excellent.
Want a Greek Salad? Fabulous choice. How about Smoked Fish Spread again? Check! Pastichio or moussaka? You’ll think you’re in Greece.
If you’re watching carbs, you can’t go wrong with the Bacon Wrapped Filet. Substitute sautéed spinach or double vegetables for the baked potato. Or see if they’ll make the Steak Diane for you—it’s a personal favorite that’s no longer on the menu, but we’ve scored it a few times since it went away.
If you want to keep it simple, the Black Angus Burgers and fries are excellent as well. And for those who want to eat lighter, our new favorite is the Chicken Salad Sandwich. Listen to these ingredients: chicken breast, celery, raisins and cashews. It’s the chicken salad you’ve been searching for. The Lemon Chicken Soup is so, so good, too.
Dinner – Tommy’s Hideaway
Tommy’s Hideaway has the secret sauce. (And hint: it might be all over the Parm Fries.) Fries? Check. Parmesan? Check. Herbs? Whatever. Butter? Pretty sure it’s all over them. The Meatballs with Ricotta are delicious, as are the burgers and pizza. And pretty much any dessert. Especially the Churros.
Parm Fries at Tommy’s Hideaway
Gulfport Brewery + Eatery – part of the Tampa Bay Beer Trail
Day 4
Breakfast – Mademoiselle Paris – French Restaurant and Bakery
I used to have to drive to SPB for French pastries. No more. Mademoiselle Paris has hit the ground running in Gulfport. It’s not their first offering either, with locations in Sarasota and AMI already.
Consistent, familiar French foods for breakfast, like Omelettes, Eggs Benedict, Crepes, Quiche, and Croissants. Paninis and Savory Crepes and sandwiches for lunch.
Lunch – V-Roll or CITGO.
Yes, I listed the CITGO on Gulfport Blvd. It might be the best Cubano you’ll ever have. Word is on a SLOW day they make about 150. They’re THAT popular. Like Annex, though, it’s a “to go” place, unless eating in a gas station store is your thing. So if you want a restaurant and an excellent Gulfport choice, I suggest V-Roll Vietnamese Rolls and Bowls. Be warned that you’re going to be in line and ordering as soon as you walk in, so you may want to look online at a menu first if you’re new to it. You can build your own but they also have some signature creations. I’ve thoroughly loved everything I’ve had and usually over-order. But it is all good the next day.
Dinner – Habana Cafe
Time for your last dinner in Gulfport. We’ve been dining at this Gulfport institution since 2002. In the restaurant world, that kind of longevity should tell you something.
Habana has options for inside dining under the sparkling, cloud-filled ceiling or outside in a private cabana. My favorite appetizer is the Drunken Shrimp. Favorite main dish is hands down: the Picadillo. Ground sirloin of beef in a sofrito of onions, bell peppers, fresh garlic and tomatoes. What’s not to like? I like it so much I will call ahead to make sure they have it. The Cuban bread is worth getting an extra order of so you can take it home to eat with your leftover Picadillo.
Now about dessert. I love flan. I’ve been obsessed with it since I first had it in 1980. Habana has not one, but two types of flan – regular Flan and Cream Cheese Flan. I like them both, but my preferred way to consume these is to order both. I dip my fork in first one and then the other, so that my is a combination of both. If I had to get just one I would get the cream cheese version. Think more “cream” and less “cream cheese” and you’ll have an idea of what it will be like.
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