Top 15 Attractions and Activities in Gulfport, Florida

Gulfport, one of the oldest incorporated cities in Pinellas County, possesses a distinctive character. The city is known for its creativity, progressive outlook, and acceptance, highlighted by a vibrant LGBTQ+ community, numerous local businesses, and an array of engaging events.

A notable aspect of this city is its walkability. Beach Boulevard features charming cottage-style architecture alongside restaurants, bars, and community events, all seamlessly integrated with a bayfront beach and the Historic Waterfront District.

In this locale, a car is not a necessity. The city also benefits from its connection to the 75-mile Pinellas Trail, which spans the peninsula, providing easy access to St. Petersburg and its cultural offerings.

1. Gulfport Art Walk

Source: Pam’s Pottery Works / Facebook

Art is deeply embedded in Gulfport’s culture, showcased at this juried event held on the first Friday and third Saturday of each month. More than 40 vendors line Beach Boulevard, presenting a variety of creations, including wood sculptures, handmade clothing, metal art, seashell crafts, clay works, and painted glass.

During the art walk, a number of local businesses, restaurants, and shops remain open, accompanied by live entertainment throughout the area.

The exhilarating ambiance and the local creativity make this event a unique experience in one of Florida’s most distinctive cities.

2. Beach Boulevard

Beach Boulevard encapsulates the essence of Gulfport, stretching from north to south, leading directly to the bayfront.

As you move south of the public library, you enter a delightful downtown area, featuring cozy cottages housing a variety of small businesses. An array of eateries to satisfy diverse tastes, alongside boutiques, galleries, and live entertainment, can be found here.

For those interested in history, the Gulfport Historical Society conducts regular walking tours from Chase Park located to the north.

The area becomes even more vibrant during the Gulfport Tuesday Fresh Market and the aforementioned art walk, which will be described later.

At the southern terminus, the iconic Gulfport Casino anchors the Historic Waterfront District, seamlessly blending with the downtown ambiance.

3. Gulfport Tuesday Fresh Market

Source: Visit Gulfport Florida’s Tuesday Fresh Market / Facebook

Each Tuesday morning, the city hosts an exceptional open-air market featuring over 50 vendors sharing their unique products.

Here, visitors can discover handmade jewelry, fresh produce, locally crafted clothing, various types of art, along with a selection of teas and flowers.

The market’s atmosphere is inviting, charming, and community-focused. It evokes a nostalgic feeling reminiscent of an era when family-owned businesses flourished.

Live performances are featured at both ends of the market, and the businesses along Beach Boulevard benefit from the increased foot traffic.

4. GeckoFest

Taking place on Labor Day weekend, the Historic Waterfront District is home to Gulfport’s largest festival, GeckoFest, which pays tribute to the city’s unofficial mascot, the gecko.

True to Gulfport’s character, the festival radiates creativity and eccentricity, with three stages showcasing live music and over 200 vendors offering art, crafts, and food.

The festivities also include a parade, street performers, a fire and acrobatics show, along with various activities tailored for children.

Each year, GeckoFest adopts a different theme, encouraging attendees to don costumes to compete for prizes.

5. Gulfport Beach Recreation Area

This park and beach area merge seamlessly with the downtown, situated along Boca Ciega Bay. Within close proximity to eateries and shops lies a picturesque stretch of white sand along calm, shallow waters.

Spanning approximately 1,000 feet, the beach is accompanied by a grassy area adorned with benches, picnic shelters, and palms.

Among the recreational facilities available are a basketball court, sand volleyball court, a skate park, and a fenced playground for children.

While it’s always pleasant to visit, the atmosphere at sunset adds a unique charm—providing a perfect backdrop to enjoy live music later in the evening.

6. Gulfport Casino

Located at the southern end of Beach Boulevard, this striking building represents a traditional casino concept, serving as a community event space.

The site’s history traces back to 1906, originally functioning as the entrance to the city dock, complete with a trolley and ferry station.

The existing structure, a WPA project dating back to 1934, sets the stage for a vast array of events and activities throughout the year.

These events encompass trade shows, dances, sporting events, auctions, private gatherings, corporate functions, fundraisers, and various concerts.

7. Veterans Park

This lovely bayside park is situated a block east of Beach Boulevard, integral to Gulfport’s Historic Waterfront District.

Veterans Park is enclosed by a recently rebuilt seawall, providing a serene environment designed explicitly for relaxation and enjoyment of the scenic views.

The park features winding paths, a shaded observation platform overlooking the water, and ample picnic tables for outdoor dining. It also serves as the venue for Gulfport’s annual Flag Day ceremony in June.

8. Clam Bayou Nature Park

Situated in the southwestern corner of Gulfport, the Clam Bayou estuary has become a beautiful natural habitat following restoration efforts completed in the early 2010s.

Where the bayou meets Boca Ciega Bay lies a serene ten-acre nature preserve, comprising an ecosystem rich in mangroves, wooded uplands, and marshes.

Exploring the mangroves reveals an abundance of wildlife, including dolphins, wading birds, and fiddler crabs. For those interested in kayaking, this location offers an ideal launching point.

The Blueways trail navigates through the mangroves, and facilities for cleaning up afterwards are conveniently located by the ramp.

9. Bert and Walter Williams Fishing Pier

This extensive fishing pier connects Gulfport Beach Recreation Area and Veterans Park, extending into Boca Ciega Bay.

Inaugurated in 2001, this structure is the latest in a line of piers dating back to 1907, and it offers free access to visitors.

Beyond serving as a fishing destination, the pier offers a pleasant area for leisurely strolls downtown, with lighting illuminating the walk after dark and providing striking views of the bay at both sunrise and sunset.

Dolphin sightings are common, especially during early visits.

10. Village Courtyard

As I wandered along Beach Boulevard, this quaint courtyard beckoned, encircled by a collection of small businesses housed in charming bungalows.

During my visit, notable establishments included Stella’s, a breakfast destination, and The North End Taphouse & Kitchen, complemented by other smaller vendors.

Outdoor seating is available for patrons, and The North End Taphouse features a stage directed towards the courtyard, offering live music several nights a week, including jazz on Wednesdays.

11. Wood Ibis Park

A short distance west of Beach Boulevard lies this delightful oasis along a lakeshore. Wood Ibis Park is aptly named due to the diverse wading bird species frequently spotted here.

During my visit, I observed an ibis, an anhinga, and a roseate spoonbill, among others documented in the area.

This four-acre park is a passive space featuring a crushed stone path around the lake that encompasses a quarter of a mile. Native aquatic plants enhance the lake’s ecosystem, while benches, pavilions, and picnic tables provide peaceful waterfront spots.

12. Gulfport Brewery + Eatery

Located in one of the quaint cottages along Beach Boulevard, this craft brewery opened its doors in 2020. At the time of my visit, I was delighted to find 19 unique beers on tap, including Sours, IPAs, Lagers, an English-style Red Ale, and a Tropical Golden Ale.

As someone who prefers malty flavors over hoppy ones, I enjoyed my Dunkles Bock, a collaborative brew with Grand Central Brewhouse.

This establishment also features a full kitchen dedicated to crafting beer-friendly dishes from scratch, offering options such as nachos, flatbreads, sandwiches, tacos, hot dogs, and traditional bar snacks like boiled peanuts and pretzels.

13. Pinellas Trail

Tracing the Pinellas Peninsula from Tarpon Springs to St. Petersburg, this 72-mile multi-use trail runs along Gulfport’s northern border.

One aspect I appreciate about cycling in Gulfport is the convenient connector trail linking the Skyway Trail along Boca Ciega Bay to the Pinellas Trail.

Once on the main trail, access to many regional attractions is straightforward, including downtown St. Petersburg, Tropicana Field, along with the Chihuly Collection and the Salvador Dalí Museum.

Conversely, the trail facilitates visits to the Tyrone Square mall before gracefully crossing Long Bayou.

14. Catherine A. Hickman Theater

This modern performing arts venue recently opened on Beach Boulevard at the northern edge of the downtown area.

The Catherine A. Hickman Theater boasts a diverse roster of events, including concerts, plays, comedy shows, seminars, and film screenings. In a city renowned for its artistic expression, this venue offers consistent and intriguing programming.

With seating for 181, the compact space provides excellent sightlines and superior acoustics. The lobby serves additionally as an exhibition area, featuring a new showcase every month.

15. Twin Brooks Golf Course

Source: City of St. Petersburg, Florida USA / Facebook

The nearest golf course to Gulfport is this nine-hole facility located on the eastern side of the city. Twin Brooks Golf Course offers an executive par 3 layout, suited for families or adults refining their iron play and short game.

Adjacent to Clam Bayou, the course features stunning grounds, highlighted by majestic live oaks draped in Spanish moss.

A driving range with covered hitting bays complements a complete practice area. Rentals are available for those without clubs, along with carts, while a pro shop and grill enhance the experience.