Gulfport has made an incredible comeback after the storms, and now’s the perfect time to explore this charming waterfront town. It’s still shining, y’all. Whether you’re a foodie, art lover, or nature enthusiast, Gulfport offers a little something for everyone. Here’s how to spend two blissful days in one of the Bay Area’s most creative and laid-back destinations.
Enjoy a weekend stay at the cute Peninsula Bed & Cocktails (2937 Beach Blvd), where you can admire the stunning yellow façade of this dog-friendly boutique hotel. It’s a piece of Gulfport history with a modern twist. Check out the eclectic, themed rooms—especially the Paloma Suite with its soft pink accents. You might even want to make a reservation to stay here next time! Book your stay and see rooms online.
Day 1: Exploring Pinellas County’s waterfront gem
Morning: Start Your Day in Style
Kick off your Gulfport adventure with a cozy coffee at Gulfperk at The Wine House (2913 Beach Blvd S). Located in a peaceful spot with beach views, this café is perfect for sipping on a signature cold brew or a refreshing lemonade. While you’re here, take a moment to relax and soak in the atmosphere—you’re in the heart of Gulfport now.
Mid-Morning: Art and History on Foot
Next, stretch your legs with a stroll to Gordon The Gecko McFly (5500 Shore Blvd S) outside the historic Gulfport Casino. This 14-foot gecko statue is now iconic in the area, a fun photo op and tribute to Gulfport’s quirky vibe. It was created by local artist Ray Domingo and unveiled during the 22nd Annual Gulfport Geckofest.
While you’re in the area, swing by the Gulfport Historical Society for a walking tour of downtown. The museum offers an in-depth look at the city’s rich history, and the tour guides will share interesting tidbits about Gulfport’s evolution from a sleepy fishing village to the artsy hub it is today.
Lunch: Vegan Delights and Eclectic Eats
Gulfport is a foodie’s paradise, and you can’t leave without trying Golden Dinosaur Vegan Deli (2930 Beach Blvd S). Even if you’re not vegan, the flavors here will blow you away. The vegan Caesar wrap and Cuban sandwich are favorites, and you can pick up some quirky merch while you’re at it. Whether you’re a plant-based eater or not, you’ll be happy you stopped by.
Afternoon: Explore the Local Markets and Art Scene
On Tuesdays, Gulfport’s Fresh Market (9 a.m. – 3 p.m.) is a must-see. It’s located along Beach Blvd, below 29th Ave S. Expect fresh produce, artisanal bread, cheeses, honey, seafood, crafts, and live music.
If you’re here on a First Friday, don’t miss the First Friday Art Walk from 5 p.m. to 9 p.m., when the streets of Gulfport come alive with art displays, music, and food. It’s a fun, juried event that attracts both emerging and professional artists, so you’re bound to discover something new and exciting.
Evening: Dinner and Drinks with a View
Wrap up your day at Pia’s Trattoria (3054 Beach Blvd S), a cozy spot that blends old Italy with Florida’s laid-back vibe. Known for its decadent pasta and romantic atmosphere, Pia’s is perfect for a date night or a special dinner out. Be sure to make a reservation—it’s one of Gulfport’s most beloved dining spots.
Afterward, stroll over to O’Maddy’s Bar & Grille (5405 Shore Blvd), where you can unwind with drinks and tasty bar bites. This spot has been a Gulfport favorite for years, offering indoor and outdoor seating with views of the water.
Day 2: Outdoor Adventures and More Gulfport Flavors
Morning: A Walk in Nature
Start your second day with a visit to Clam Bayou Nature Park (29th Ave S & Miriam St S). With over 10 acres of nature trails, boardwalks, and observation decks, it’s the perfect spot for a relaxing morning walk or bike ride. The park also has canoe and kayak launches if you want to get out on the water and enjoy expansive views of Clam Bayou and Boca Ciega Bay.
Late Morning: Brunch with a Twist
After your walk, head to Sumitra Espresso Lounge (2838 Beach Blvd S) for a laid-back brunch. This Mediterranean-themed café offers everything from espresso drinks and teas to CBD-infused beverages. The highlight, though, is their selection of gluten-free and vegan pastries. Be sure to try the Mayan cacao elixir or a rich hot chocolate.
Afternoon: More Local Flavors
For lunch, make your way to 1 Chick 1 Bro (1431 49th St S), a small Venezuelan gem offering some of the best arepas you’ll ever have. The seafood options and appetizers, including empanadas and tequenos, are also fantastic. The blue-painted restaurant has a cozy, colorful vibe, making it a perfect spot for a casual, flavorful meal.
After lunch, walk around the Gulfport Beach Bazaar (3115 Beach Blvd S), where you’ll find coastal decor, souvenirs, unique gifts, and more. It’s the ideal place to pick up something special to remember your Gulfport trip.
Evening: A Night of Music and Local Brews
No visit to Gulfport would be complete without checking out Gulfport Brewery (3007 Beach Blvd S). This pet-friendly brewpub offers a rotating selection of craft beers, along with a fun atmosphere. Grab a pint, and be sure to try their giant can nachos—they’re a crowd favorite. Check their Instagram for live music events happening throughout the week.
For dinner, end your Gulfport journey at Julio’s Empanadas (2201 49th St S). This local eatery, housed in a converted gas station, serves some of the best empanadas and salsas in town. The Coco Rico Chicken is a standout dish, and don’t forget to try the tres leches cake—it’s a sweet end to your Gulfport adventure.
See even more things to do in Gulfport on Visit St. Pete-Clearwater’s website. 
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