One of the oldest incorporated cities in Pinellas County, Gulfport is a place with its own personality. At once creative, progressive and open, the city has a large LGBTQ+ community, many local businesses, and a lot of fun events.
One of many things that won me over about this city is how walkable everything is. For example, Beach Boulevard, with its cottage-style architecture and restaurants, bars, and community events, is entwined with a bayfront beach and Historic Waterfront District.
This is one place where you do not need a car to get around. Even less so, because the city is connected to the 75-mile Pinellas Trail, which serves the entire peninsula, putting you within easy reach of St. Petersburg and its internationally renowned culture.
1. Gulfport Art Walk
Art is in Gulfport’s veins, as you’ll see at this juried event on the first Friday and third Saturday. Lining Beach Boulevard are 40+ vendors, displaying everything from wood sculpture to handmade clothing, metal art, seashell crafts, clay pieces, and painted glass.
During the art walk, many of the businesses, restaurants, and shops are open, and there’s live entertainment all around.
Indeed, part of the joy of the event for me was soaking up the atmosphere and witnessing some local color in one of Florida’s most unique cities.
2. Beach Boulevard
I think Gulfport’s essence is captured by Beach Boulevard, running north to south, down to the bayfront.
South of the public library you’ll enter a cozy downtown area, fronted by cottages home to a diversity of small businesses. There’s an assortment of eateries for all palates, as well as boutiques, galleries and live entertainment.
For some historical background you can join one of the regular walking tours. These are given by the Gulfport Historical Society, based at Chase Park to the north.
There’s even more life during the Gulfport Tuesday Fresh Market, and the art walk, which I’ll talk about later.
At the south end, the iconic Gulfport Casino is the anchor for the Historic Waterfront District, which merges with the downtown area.
3. Gulfport Tuesday Fresh Market
The city hosts a fantastic open-air market every Tuesday morning. More than 50 vendors come out once a week to display their unique offerings.
You can find almost anything, including handmade jewelry, fresh produce, locally-made clothing, every type of art, and a variety of tea and flowers.
The atmosphere of this market is friendly, quaint, and community-oriented. To me it felt like something from a different time, when everyone shopped in little family-owned businesses.
Live entertainment occurs at both ends of the market. The shops and eateries along Beach Boulevard also benefit from the extra foot traffic on this day.
On Labor Day weekend, the Historic Waterfront District hosts Gulfport’s biggest festival. GeckoFest is in honor of the city’s unofficial mascot, the gecko.
Fitting for Gulfport, the event has a creative and quirky vibe, with three stages of live music and 200+ art, craft and food vendors.
Some of the many things going on around the district include a parade, street performers, a fire/acrobat show, and all kinds of activities for kids.
GeckoFest has a different theme each year, and you’re encouraged to show up in costume to compete for prizes.
5. Gulfport Beach Recreation Area
The downtown area mingles with this park and beach on Boca Ciega Bay. All within a few steps of the restaurants and shops there’s a pleasing arc of white sand, on calm, shallow waters.
The beach is around 1,000 feet long, and trimmed by a grassy area dotted with benches, picnic shelters and palms.
A few of the recreation amenities here include a basketball court, sand volleyball court, a skatepark, and a fenced children’s playground.
There’s never a bad time to be here, but I think there’s a magic to this place at sunset. You can watch the sun go down over the bay before heading off to catch some live music.
6. Gulfport Casino
At the southern end of Beach Boulevard, this imposing building is a casino in the old sense of the word. That is, a community event space, and this is a role that the building continues to fill.
The history of the site goes back to 1906 as the entrance to the city dock, with a trolley/ferry station and ticket office.
The current building is a WPA project from 1934, and sets the scene for a ton of events and activities all year.
These include trade shows, dances, sports events, auctions, private functions, corporate events, bar mitzvahs, fundraisers, and a number of concerts.
7. Veterans Park
Integral to Gulfport’s Historic Waterfront District, this gorgeous bayside park is a block east of Beach Boulevard.
Veterans Park is contained by a sea wall that had recently been rebuilt when I was here. This is one of a few public spaces in Gulfport designed solely for relaxing and appreciating the scenery.
As well as winding paths, there’s a shaded observation platform on the water, and plenty of picnic tables for a scenic lunch al fresco. The park is the setting for Gulfport’s annual Flag Day ceremony in June.
8. Clam Bayou Nature Park
In the very southwest of Gulfport, the Clam Bayou estuary is a beautiful natural environment reborn following restoration work in the early 2010s.
Where the bayou joins Boca Ciega Bay there’s a ten-acre nature preserve. This tranquil property is composed of mangroves, wooded uplands, and marsh.
Wandering the mangroves, I was stunned by the profuse wildlife, from dolphins to wading birds, and fiddler crabs. If you’re in town for some paddling, there’s no better place to launch a kayak.
The Blueways trail here guides you through the mangroves, while there’s a hose by the ramp to rinse off afterwards.
9. Bert and Walter Williams Fishing Pier
Between Gulfport Beach Recreation Area and Veterans Park there’s a long fishing pier reaching out into Boca Ciega Bay.
Unveiled in 2001, this is the latest in a long succession of piers, reaching back to 1907. The structure is 521 feet long, and unlike a lot of similar piers can be accessed for free.
Not just for fishing folk, this is a wonderful spot for a continued stroll downtown. There’s lighting after dark, while the vistas over the bay are stunning at both sunrise and sunset.
You’re likely to see dolphins too, especially if you visit early in the day.
10. Village Courtyard
Strolling along Beach Boulevard, I was drawn into this small courtyard, enclosed by a group of small businesses in cute little bungalows.
When I came through, the anchors were Stella’s, a breakfast spot, and The North End Taphouse & Kitchen. These were accompanied by a cluster of smaller vendors.
There are outdoor tables for the restaurants and bars here, while The North End Taphouse maintains a stage facing the courtyard. You can catch live music here several nights a week, including a jazz night on Wednesdays.
11. Wood Ibis Park
A couple of blocks west of Beach Boulevard there’s a lovely little oasis on the shores of a lake. Wood Ibis Park is an accurate name, given the wide variety of wading birds routinely seen here.
In my few minutes at the park I saw an ibis, an anhinga, and a roseate spoonbill, but many more have been documented.
On four acres, this is a passive space, with a crushed stone trail around the lake adding up to a ¼ mile. Native aquatic plants help keep the lake’s ecosystem healthy, while there are benches, pavilions and picnic tables by the water.
12. Gulfport Brewery + Eatery
In one of those adorable cottages along Beach Boulevard, this craft brewery opened in 2020. There were 19 beers on draft when I was in town, including Sours, IPAs, Lagers, an English-style Red Ale, and a Tropical Golden Ale.
As someone who opts for malty beers over hoppy ones, I was pleased with my Dunkles Bock, a collaboration with Grand Central Brewhouse.
As the name tells you, this establishment has its own kitchen, making beer-appropriate bites from scratch. Think nachos, flatbreads, sandwiches, tacos, hot dogs, and classic bar snacks, from boiled peanuts to pretzels.
13. Pinellas Trail
Running along the Pinellas Peninsula, from Tarpon Springs to St. Petersburg, this 72-mile multi-use trail skirts Gulfport’s northern line.
Something I love about cycling in Gulfport is the handy connector trail between the Skyway Trail on Boca Ciega Bay and the Pinellas Trail.
Once you’re on the main trail you can reach many of the area’s top attractions with ease. This goes for downtown St. Petersburg, Tropicana Field, and the likes of the Chihuly Collection, and the Salvador Dalí Museum.
In the other direction, the trail serves the Tyrone Square mall, before crossing Long Bayou in magnificent style.
14. Catherine A. Hickman Theater
A recent arrival, this modern performing arts stage is on Beach Boulevard at the north end of the downtown area.
The Catherine A. Hickman Theater hosts a packed schedule of concerts, plays, comedy, seminars, film screenings, and more. In a city known for its artistic flair, this venue always has something interesting going on.
This is a compact venue, with seating for 181, perfect views and high-quality acoustics. The lobby also doubles as an exhibition space, with a new show every month.
15. Twin Brooks Golf Course
The closest golf course to Gulfport is this nine-hole facility on the eastern side of the city. Twin Brooks Golf Course is an executive par 3, ideal for families or adults working on their iron play and short game.
Near the head of Clam Bayou, the course is on beautiful grounds, growing some grand old live oaks streaked with Spanish moss.
There’s also a driving range with covered hitting bays, as well as a full practice area. If you don’t have your own clubs you can rent them, along with carts, while there’s also a pro shop and grill.