An incredibly orange house in Gulfport with a picket fence and gone fishing signs on the door

Gulfport’s splashy homes and businesses add color and pizazz to the city’s streets. Many local homeowners love to show off their personal style through paint, and their creativity fits right into Gulfport’s joi de vivre.

proudly weird


The friendly, small waterfront community of Gulfport has been celebrating its weirdness since before it was cool to do so. It’s also been a long-time haven for the LGBTQ+ community. The city’s eclectic collection of artists, writers, musicians and small business owners along with its walkable downtown and sparkling bayfront make this a must-visit place. 

Things to Do

Spend the day wandering along Beach and Shore boulevards, popping in and out of shops and galleries, sampling delicious food and taking in local history as you walk past charming old buildings. It’s likely that you’ll hear live music coming from Art Village Courtyard or Caddy’s Gulfport as you pass by. 

Ladies dressed in green masks and costumes having fun at Geckofest in Gulfport

Small-town Gulfport has a larger-than-life vibe, with plenty of art fests, parades, farmers markets and other events to keep things lively. Stroll through downtown on most any weekend to join in the fun.

colorful, intricately painted masks for sale at a festival in Gulfport

Many local artists live and work in Gulfport. Meet them and buy their art and other handcrafted goods at local galleries and festivals.

Stroll to the end of Beach Boulevard to check out the historic Gulfport Casino. Set on the water’s edge, it’s a casino in the old-school sense of the word - an event venue where you’ll find swing-dancing and tango classes as well as other entertainment. Stroll to the back to see the tomb of Morris the Cat, the beloved feline who became the city’s unofficial mascot (and whose spirit is said to wander near the casino). Walking tours of the downtown are offered by the Gulfport Historical Society (check out the museum, too, while you’re in the area).

Looking for some fun on or near the water? The beach here isn’t huge, but it’s quiet and relaxing, and its volleyball courts are a popular spot. Nearby, the massive playground and skate park near the Gulfport Recreation Center is popular with families. If you want to get out on the water, check out the City of Gulfport’s Municipal Marina, where you can find boat tours or rent a kayak to take a tour of Clam Bayou Nature Preserve.

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Events & Festivals

Gulfport is renowned for its events. GeckoFest jubilantly marks the end of summer over Labor Day weekend with live music, more than 200 vendors, kids’ activities and more. The city’s  First Friday Art Walk draws locals and visitors alike in search of handcrafted treasures. There’s the Gulfport Tuesday Fresh Market for local produce and flowers. And on any given day of the week, you might spot an impromptu parade marching by to celebrate (or protest) any number of things.

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Gulfport may have a reputation as a laid-back village, but there are plenty of good restaurants and watering holes here.

a woman in a tank top holds a large arepa in her hands

1 Chick 1 Bro is a new Venezuelan eatery in tiny Gulfport.

a smiling server waits at the entrance of Pia's Trattoria, a cozy Italian restaurant in Gulfport; the building is painted bright yellow and a table is outside

It doesn't get any cozier - or any more delicious - than at Pia's Trattoria in downtown Gulfport. Choose indoor or outdoor seating, and expect a relaxed evening.

Places to Stay

Gulfport’s laid-back indie vibe carries over to its accommodations. With its friendly staff and waterfront views, Sea Breeze Manor on Shore Boulevard is an inviting option. Peninsula Bed & Cocktails, a dog-friendly boutique hotel built in 1905, is in the heart of downtown.

See All Places to Stay in St. Pete/Clearwater

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