Gulfport guide: Charming restaurants, lively bars and funky festivals

Note: This guide first appeared in our email newsletter series, One Day in Tampa Bay. Subscribe to that newsletter and check out our other offerings at tampabay.com/newsletters.

It’s hard not to fall for the undeniable charm of Gulfport. The city’s friendly, bohemian atmosphere and funky, laid-back vibes make it one of the region’s most beloved small towns.

Boasting beach access, parks, restaurants and a lively bar and music scene, Gulfport is becoming one of the hottest areas for real estate. But even if you can’t afford to buy your dream home here (it’s OK, neither can we), there’s plenty to do on a day trip and more than enough reason to return.

Times tip: Gulfport is home to a number of outdoor markets and festivals, including GeckoFest in September, the monthly First Friday Art Walk and the weekly Gulfport Tuesday Fresh Market.

Start here

The breakfast at Gulfport institution Stella’s is always a solid bet, as is the restaurant’s signature fried green tomato BLT, served on crusty sourdough toast with spicy mayo. The spot also sports a mean mimosa and Bloody Mary selection, including a spicy bacon and jalapeno version and an Asian-inspired take made with soy sauce, wasabi and cucumber.

For a solid coffee buzz, head over to GulfPerk, a quaint little coffeehouse and breakfast spot featuring espresso drinks and signature creations, including the Cookie Butter Latte and snacks like breakfast sandwiches, bagels and avocado toast.

Map

Click here to see the full map.

Transportation

Downtown Gulfport is easily traversed by foot, bike or car.

Parking

There’s free street parking all along Beach Boulevard S and in front of Gulfport Beach Park, on Shore Boulevard.

Bathrooms

You’ll find public restrooms at Gulfport Beach Park.

Shop and stroll

There’s no shortage of boutiques to choose from along Beach Boulevard S, but we’re partial to the eclectic collection at the Gulfport Beach Bazaar, which features a huge assortment of vintage collectibles and antiques, refurbished furniture, Christmas ornaments, beach accessories and jewelry. Tucked among all those funky finds? A U.S. Post Office, in case you’ve got a package to send or a document that needs notarizing.

Pick up something for your pooch at nearby Paw Paw’s Pet Boutique. You’ll find everything from doggie “cigars” (Puparillos) to dog and cat couture, snacks and all manner of pet paraphernalia.

Get outside

Gulfport boasts plenty of activities for the outdoors enthusiast, especially kayakers and paddleboarders. Gulfport Beach Park, on Shore Boulevard S between 54th and 58th streets, is a lovely spot for a picnic or sunset hang. There’s almost always some action to catch at the beachfront volleyball court. Wander the boardwalk trails through the mangroves or rent a kayak at Clam Bayou Nature Park (29th Avenue S and Miriam Street S), which is just a five-minute bike ride from downtown Gulfport.

Unwind

Thirsty? Grab a seat at one of the picnic tables outside Gulfport Brewery, which boasts a rotating selection of 16 beers on tap — including our favorite, a New England-style hazy pale ale called the Hippie Oasis. There’s also a great food menu if you need something to soak up the suds. We love the house flatbreads, especially the one topped with bacon and Brussels sprouts.

For beer lovers, there’s also the North End Taphouse facing a shared courtyard that hosts frequent live music acts. Nearby cozy coffeehouse SumitrA serves tea, espresso, wine and CBD-infused drinks.

Make a night of it

Gulfport’s restaurant scene is always evolving, but Pia’s Trattoria has been a neighborhood mainstay since 2005 — and for good reason. The beloved Italian restaurant is among the most romantic places to dine in the Tampa Bay area, and its rustic Italian specialties (including some truly excellent pasta dishes) never disappoint.

Vegan diners will love Golden Dinosaurs, where a plant-based menu includes cheeky takes on comfort food favorites sans meat. Think “pastrami” Reuben sandwiches, Beyond Meat burgers and chili dogs.

O’Maddy’s Bar and Grille, down near the water, is one of the best spots in town to people-watch. (It’s a real neighborhood hang.) The place also has a great food menu, including plenty of surf and turf options. Don’t skip the crab cake sandwich, featuring a whopper of a crab cake on a pretzel bun with lettuce, tomatoes and a chipotle mayo. If you’re feeling up for tunes after dinner, the bar hosts karaoke nightly.

For dinner and a show, the Tiki Bar and Grill hosts live music most nights. It serves one of the best slices of key lime pie in town, too.

Check out our other local guides

• Downtown Tampa guide: How to explore Riverwalk and beyond without a car
• Pinellas County beach guide: Where to eat, drink and relax along the Gulf
• Safety Harbor guide: Plan a day of indulgence, from pizza to public art
• Tarpon Springs guide: Explore Greek food, the Sponge Docks and beyond

Contact Gabrielle Calise at gcalise@tampabay.com. Follow @gabriellecalise. Contact Helen Freund at hfreund@tampabay.com. Follow @helenfreund.