4 Day Dining Guide to Gulfport Florida

2021 Update Our 4-Day Dining Guide to Gulfport

The year that shall not be named caused many upheavals in the restaurant world.  It also changed the average length of stay for most guests staying at our vacation homes.  Quick trips are less common, providing us with an incentive to expand our 3 day dining guide to 4.

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

DinnerSiri’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

BreakfastStella’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.

LunchO’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.

DinnerPia’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

Tutto Bene’s Caesar Salad

Day 3

Breakfast – GulfPerk

Charming newcomer Gulf Perk has just the vibe Gulfport needed.  Along with the coffee options you’d expect – lattes, mochas and caps – there are pastries, muffins, bagels, the obligatory avocado toast and breakfast sandwiches. 

And just in case you miss breakfast, you can try GulfPerk After Dark.  Charcuterie & wine. Thursdays through Saturdays.

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.

DinnerBackfin Blue or Sea Dog Cantina

Backfin is a Gulfport institution and always buzzing. Get there early if you can pull yourself away from the beach!

We rotate between ordering the Backfin Blue Jumbo Lump Crab Cakes, the Homemade Meatloaf (wrapped in bacon and stuffed with gorgonzola) and the Slow Roasted Choice Prime Rib. The prime rib sells out quickly—one of the reasons early dining is so popular.

Start with the Fish Spread (of course), the Crab Martini or the Puree of Corn and Crab Chowder. The Crab Cake Starter is also solid option if you’re not having the crab cakes as your entree.

We also love indulging in their loaves of warm brown bread with butter. Get an extra to take home for a late-night snack!

Backfin is still open on a fairly limited basis after Covid, open Thursday through Sunday only and table service is very limited.  (The restaurant isn’t very large to begin with, making the seating spacing a constraint.)  So we provide a worthy alternate Sea Dog Cantina, located just down the street.

Sea Dog is part of the Sea Dog brewing family, but the menu is uniquely Gulfport.  My personal favorites are the House Queso Fundido, the Chicken Tortilla Soup, Mexican Street Corn Caesar Salad, the Chile Braised Beef Brisket, and the Enchiladas made with the chile beef brisket.  They have some really creative margarita blends, including a couple on tap!

Beautiful Interiors at Sea Dog Cantina

Gulfport Brewery + Eatery – part of the Tampa Bay Beer Trail

Day 4

Breakfast – Gulfport Family Restaurant

Consistent, familiar southern breakfast foods at prices that won’t break the bank.  Pancakes, eggs, sausage, bacon, grits, potatoes, corned beef hash, country fried steak, pork chops and chopped sirloin are all on the menu. Thick Texas Toast is dipped in their French Toast batter and grilled.  Omletes are available too.

And that’s just breakfast.  They also serve lunch, with tasty dishes like Greek salads, cheeseburgers and spaghetti and meatballs.  Dinner is just what you’d expect at a diner, with food like pork chops, liver and onions and roast turkey.  (And more!)

Lunch – Salty’s Sandwich Bar

We thought we’d “sandwich” the new Salty’s concept in-between two Gulfport old-timer’s.  (Get it??) Anywho, Salty’s Sandwich is located in the space that previously belonged to Tangelo’s.  Home to subs, a Fried Bologna Sandwich, a Grilled Triple Cheese Melt and of course, Salty’s Cubano.  (My post on area Cubanos is coming soon!)

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.

Gulfport Food and Dining Home

The Home page has links to all of our guides and posts related to food in Gulfport

Gulfport Restaurant Guide

Our Gulfport Restaurant Guide has the inside scoop on our recommendations for restaurants in Gulport

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