This Artsy Florida Town Lives by the Motto “Keep Gulfport Weird”

Our research is editorially independent but we may earn a commission for purchases made through our links.

A small beach town with a big heart, Gulfport is one of Florida’s most underrated vacation destinations. Popular for their year-round events and eclectic ambiance, Gulfport is located on the south end of the Clearwater peninsula near St. Petersburg. With a motto like “Keep Gulfport Weird,” how could you not love this town?


Look out for our newsletters in your inbox soon.

Gulfport, Florida

Located on the Boca Ciega Bay, Gulfport is lined with funky independent shops and a beautiful beach, boasting a colorful personality that attracts people from around the state. You won’t find chain stores around these parts or even parking meters, just a warm welcome from the friendly locals.


First-time visitors to this Old Florida-style village are encouraged to walk along the historic district on Beach and Shore Blvd to take in the view of Tierra Verde across the bay. Shop for unique treasures from an array of local artwork on display, or simply take a stroll along the brick-paved streets and take in views of colorful cottages nestled under old oaks draped in Spanish moss. Wrap up your day with a walk to Williams’ Pier, where a colorful sunset show and gentle evening waves will take your stress away.

Gulfport, Florida

Known for its annual events, time your visit with the popular GeckoFest at the end of the summer. Here you’ll find a kaleidoscope of colors at this circus-like atmosphere with a combination of street performers, crazy costumes, and live music, a fun-loving event that was designed as a tribute to the town’s favorite lizard. You can also attend one of the monthly Gulfport Art Walks, where Beach Blvd comes alive with local artists, vendors, and musicians, while those looking for fresh produce, seafood and cheeses can visit Gulfport’s Tuesday Fresh Market.

Gulfport, Florida

If you’re in need of a dose of nature, head to the Clam Bayou Nature Preserve to spot bird marine and plant life and soak in the cool breeze of the natural surroundings along the walking path. A beautiful 10-acre nature preserve, here you’ll find plenty of appealing outdoor adventures to indulge in, such as hiking, canoeing, and kayaking.

Gulfport, Florida

In Gulfport, you’ll discover a local culture filled with artsy shops, a thriving arts scene, a lineup of easy-going waterfront restaurants, and most importantly – quirky vibes that will lure you in time and time again. There’s always something going on in this small-town gem, where its unique Gulfport-style hospitality is second to none.