Gulfport, Florida

You may look at the Master List of restaurants below and wonder, “how in the heck can a town the size of Gulfport have so many outstanding restaurants?” Could Beth be exaggerating, just a tiny bit?

Nope, I’m not! Gulfport is a small town and these eclectic and delicious restaurants are one of the reasons the town of our size is able to draw as many tourists as it does, from around the Pinellas Peninsula and across the Bay.

Below, I’ve carefully selected restaurants that I know will add to your Gulfport experience. No tourist traps! These are spots you’ll think about after you go home, staffed with good people who turn out some truly amazing dishes that will stick with you.

We hope you’ll try as many as you can! (If viewing on phone text and descriptions follow the pics!)

Only have a few days to spend in Gulfport? Then follow our 3 Day Dining Guide to Gulfport.  You can’t go wrong!

Despite the fact that they’re closed on Tuesdays and Wednesdays (the nerve!) Backfin Blue is one of my favorites. Why, you ask? Let me count the reasons: crab cakes, meatloaf, the Mr. Oscar (the day’s fresh catch, expertly prepared), crab and corn chowder, prime rib…I could go on! 

Backfin Blue is tucked in a charming old house on Beach Boulevard. Dine outside if you can: there’s better acoustics and you may be treated to a serenade by a crooner next door at the Peninsula Inn.

2913 Beach Boulevard South
727-343-BLUE

Closed Tuesdays 

Pia’s and Backfin tie for my favorite Gulfport restaurant. Pia’s food rivals anything I’ve had in Italy, and I ate well in Italy! Over the years, Pia has expanded from a tiny eatery to include a few indoor dining rooms as well as an outdoor courtyard and sidewalk dining.  This is a good thing: the word is out and Pia and the staff deserve all the compliments they get from happy diners. 

The Lasagna Bolognese is my staple but half the time I’m diverted from that option by a mouthwatering Daily Special. For appetizer enthusiasts, the salads and soups are equally delicious.  

3054 Beach Blvd. S.
(727) 327-2190

Open every day; hours vary so check website

I’d be lying if I said I wasn’t suspicious of Smokin’’ J’s at first. I mean, they’re from Texas. Why did they leave the land of BBQ?! But after couple of meals here, I no longer care why or how they ended up in Florida—I’m just glad they did.

Smokin’ J’s has the secret sauce (literally, with two options: sweet and hot) and the tasty sides (green beans, mac and cheese, etc.) that you’d expect of a BBQ joint. Their brisket is actually my least favorite, as it is a little too dense and dry for me. But the ribs, smoked sausage and pulled pork (smoked for 14-16 hours and then hand-pulled) will satisfy any carnivorous craving. 

If you’re in town for the holidays, call ahead for a smoked turkey and take a load off!

If you care, take on the Smokin’ J’s BBQ Challenge.  Win, and this challenge is free; lose and you’ll pay $49.  To win, you have to consume the following in one hour: a pound each of sliced brisket, pulled chicken, pulled pork, sliced sausage, a boneless rack of ribs, and pickles and onions on a bun with a jalapeno to top it all off.  See the pictures.  And bless your little heart if you try!

5145 Gulfport Blvd S      

727-329-8624

Closed Monday and Tuesday

O’Maddy’s is almost too popular for its own good.  It’s always crowded, but that’s because the food is always good.

Life always presents us with tough choices, but at O’Maddy’s, you don’t have to think too hard.  Whatever appetizer you pick (Frank’s Fried Fish Nuggets, Collin’s Irish Chips) is bound to be great.  Come for drinks and choose from inventive concoctions (Gulfport Guava Breeze, Key Lime Pie Martini) and beach cocktail classics.

O’Maddy’s knows how to feed a crowd in a timely fashion and they stay open late.  Really late.  3 am!  And some dishes on the menu are named after locals. You may be able to thank them in person.

5405 Shore Blvd S        

727-323-8643

Open daily hours vary

Habana cafe has been around a long time, but it’s never lost sight of its passion for delicious, authentic Cuban food.  And the world has taken notice: Chef Jo Hastings won the 2003 Signature Desserts Award from Southern Living Magazine for her flan.  Other local awards include Best Cuban Food and Best Cuban Food in Tampa Bay Area.

My favorites are the Drunken Shrimp and the Papas Rellenas for starters, and the Picadillo for an entree. For dessert, it’s a no brainer: the award-winning flan. I’ve had a thing about flan ever since I first had it in college.  Believe me – I’ve tasted lots of it, and Chef Jo’s tops the list.

Stop by and check it out! And be sure to visit the upstairs gallery to see the amazing bird art.

5402 Gulfport Blvd S      

727-321-8855

Closed Sunday

One of the pricier dining options in Gulfport, but hands-down worth it, even just for the classic beach vibe on Boca Ciega Bay.

One night we ate a meal comprised entirely of the delectable assortment of appetizers.  Try the dates stuffed with goat cheese, wrapped in prosciutto and drizzled with balsamic. The fish tacos also get rave reviews from me. 

The outdoor seating area is perfect for gazing out over the waterfront and listening to the shorebirds or the local live music.  Draft beer, craft beers, bottled beers, sangria – what’s not to like?

5519 Shore Blvd S          

727-498-8826

Closed Sunday

This is important, so don’t say I didn’t warn you: Mid Peninsula Seafood is closed on Sundays.  Yep, that’s right, the people at the fish place go fishin’ on Sundays.  So you’ll have to eat your meal here Monday – Saturday.  Or, if you’re feeling ambitious, buy your own fresh fish here and give it a shot yourself – Mid Peninsula has both a restaurant and a market. 

Not sure which fish to buy? Visit their Fish School and learn about the varieties they usually have fresh in stock.  The homemade Fish Spread (one of my favorite dishes so you knew I’d recommend it) is wonderful and so are the conch fritters.  The crab cakes are made with the real thing – no “krab” here!

And here’s the tip of the day: get extra cornpups.  All dinners come with them, but we promise you’ll want more.

400 49th St S, St Petersburg        

727-327-8309

Closed Sunday

Dine in, dine out, sing along, watch some sports. And did we mention you can actually hear your dining companions when dining indoors at Neptune Grill? That is, if there’s time to talk to your group while you’re busy stuffing your face with Greek goodness.

I recommend trying the Pastichio. No matter if you’ve sworn off meat, pasta or Bechamel sauce.  You’re forgiven for cheating just this once.  The Neptune Chicken is a delightful mixture of sauteed chicken breast, green peppers, spinach, tomato, basil, Kalamata olives and feta cheese.  The good ole American cheeseburger is everything you want it to be.  Can you tell I’m a repeat customer?

5501 Shore Blvd S        

727-623-4823

Open daily hours vary check website

How can Siri’s be so good at both burgers and pizza, you ask? Maybe it’s because they make everything in house. I say: stop asking questions and just enjoy the food! 

My recommendation: try the Hawaiian Burger or Smoked Salmon Pizza.  Or take a gander at our Siri’s recommendations in our 3 Day Dining Guide to Gulfport.

2813 Beach Blvd S        

727-258-4949

Open daily hours vary

Stella’s serves breakfast and lunch all day long.  Come dine in the shade inside, or feast outside with a view of Boca Ciega Bay and Gulfport Casino.  Stop in for a simple breakfast, or choose from specialities like the Gulfport Beach Salmon Lox Platter.

Or…drum roll please…a flight of mimosas!

3119 Beach Blvd S     

727-498-8950

Open daily 7am – 2pm

Tangelo’s is a lovely gathering spot serving delicious Caribbean Cuisine. Dine inside or out at this welcoming hub in the heart of Gulfport’s Waterfront District.

Tangelo’s famous Jerk Chicken was featured on the Cooking Channel’s Beach Bites with Katie Lee! (Are you starting to see what I mean? Gulfport has a fantastic concentration of talented chefs and a wide assortment of cuisines.)

Homemade sangria and tropical mimosas are a huge draw, especially for Sunday brunch. But don’t forget to put down the glass and order favorites like Island Custard French Toast or Baha Mac and Cheese.  Egg, cheese, and macaroni custard—what’s not to like?

For dinner the roasted Cuban-style pork and the Caribbean Meatloaf are hits with me.  Oh, and grab a side of the Yucca Fries.  They’re the real thing.

For dessert the key lime pie with Oreo cookie crust is a winner.  Although the serving size is a little smallish for this dessert lover.

3121 Beach Blvd S          

727-894-1695

Closed Mondays

Who can refuse a meal at a restaurant with a resident ghost? Or one that’s been awarded Best of the Beaches and Best of the Road by Rand McNally? Well, not me! And no where else will you find more of that Old Florida feeling than by sitting on a veranda at Isabelle’s.

Try southern staples like the braised short ribs, chicken and waffles, crab cakes, Low Country shrimp and grits and the cornbread and biscuit basket.  And…Patty’s Famous Key Lime Pie for dessert.

2917 Beach Blvd S            

727-346-9800

Closed Mondays

This little gem is tucked away at the back of the Art Village Courtyard in a little green building. It’s a family establishment—you’ll often see T and the kids there—and it’s certainly not a fast food joint. Everything is made when you order it and definitely made with love. 

My hands-down favorite is the breakfast sandwich (or “breakfast sammy”) on house-made flat bread, but I also love the Mic Mic, a homemade English muffin with eggs and ham, and the Lisa bowl, hash browns topped with eggs (scrambled or poached) and either cheddar or goat cheese, plus chives. If you like a sweet drink, try the salted caramel coffee.

2908 1/2 Beach Blvd S        

727-331-5253 

Closed Mondays

Looking for some casual chow? Yummy’s is the place to get Chicago dogs or sandwiches, followed by a scoop of ice cream. It’s under new ownership, so we’ll update soon! If you try Yummy’s, let us know what you think.

2914 Beach Blvd S            

727-321-9869 

Open Tues – Sat 11am – 7pm, Closed Sunday and Monday

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