By  Mike Miller Updated July 17, 2023

Gulfport, Florida Things To Do, Lodging, Dining, & Real Estate At End Of Article

The City of Gulfport is a small incorporated city in the heart of the Tampa-St. Petersburg-Clearwater metropolitan area.  It is in Pinellas County, and its southern border fronts on Boca Ciega bay.

Gulfport CasinoGulfport Casino

It is surprising to find a piece of Old Florida right in the middle of this busy urban environment. 

Gulfport WaterfrontGulfport Waterfront

This small town of 12,000 is nestled along Boca Ciega Bay not far from where you take the impressive Sunshine Skyway across Tampa Bay down into the Bradenton and Sarasota region.


The town is actually a tad older than St. Petersburg because a railroad man named Peter Demens built his Orange Belt Railway from Central Florida to this location.

It was originally named Disston City in 1884 after Hamilton Disston, an early northern businessman who had purchased millions of acres of Florida land.

Demens pushed the railroad on south and in 1888 named the end of the line St. Petersburg after his home town in Russia.

Disston City was renamed Bonifacio, then Veteran City, and finally in 1910 it settled on the name Gulfport.

In 1930 the citizens built the Gulfport Casino as a community center and entertainment venue.


Gulfport has an "Old Florida" feel to it, especially around its waterfront district.

Street Festival in GulportStreet Festival in Gulport

Many of the original old cottages still remain, and the neighborhood is sprinkled with charming little shops and restaurants.

You won't find big chain stores here, just an eclectic mix of independent shops. 

In fact, there are no parking meters as the town wants to keep that small town yet "big heart" friendly feeling.

The streets are lined with ancient oak trees and some of the residential areas still have brick streets.

Gulfport CottageGulfport Cottage

It's not surprising that Gulfport attracts the creative crowd - many local artists, musicians, craftspeople and even local authors.

These people are fascinated by Gulfport's charm and tropical ambience and the many events that take place. Almost every day is a "celebration."

Locals and tourists crowd the streets on the first Friday and third Saturday of each month for a family-friendly celebration called the "Gulfport Art Walk".

In recent years they've added a "fresh market" every Tuesday and Saturday featuring local produce, crafts, and live entertainment.

There are no admission fees, parking is free, and the city runs free trolleys throughout the city for easy access to everything.

(Note:  during Covid outbreaks the trolley is sometimes shut down.)

Gulfport Casino BallroomGulfport Casino Ballroom

The center of community activity is the old Gulfport Casino Ballroom located on the waterfront at the base of the city pier.

This is not a gambling casino, but a throwback to an era when casinos were places to gather and socialize.

The Casino dates back to the early days of the city and hosts various dance events five days a week on its 1930s era dance floor.

These events are well attended by fun lovers from St Pete, Tampa, Clearwater and the entire Tampa Bay area.

The historic building and grand ballroom are steps away from the white sand of the Gulfport beach.

Peninsula InnHistoric Peninsula Inn

In addition to dance lessons and events, many people find it's the perfect place for a beach wedding and reception or other large event.

There are even boat slips to allow visitors to arrive by water, along with a full service bar.

Fishing is one of the favorite pastimes of locals and visitors and the area provides this as well.

Williams Pier, GulfportWilliams Pier, Gulfport

Williams Pier is a prime example, having been built in 1907 and fully remodeled to include an extension of over 500 feet to allow for deeper fishing, exterior lighting, seating and a fish-cleaning table.

There are several nice smaller parks to enjoy in the area, including Clymer Park, which has a sculpture garden, a recreation center and a large skate park.

Also popular is the larger Clam Bayou Nature Park, with it's 10 acres of peaceful nature preserve, walking trails, canoe/kayak launch and beautiful views of Boca Ciega Bay.

Gulfport is also famous for its many good restaurants. Several travel magazines have voted the town as one of the best food cities in Florida.

The small city area is less than 4 square miles, and more than a dozen restaurants and small local businesses line Beach and Shore Boulevards, running along the waterfront.

There are a couple that are fine dining although many have a more laid-back atmosphere. A great way to spend an evening is strolling through the area enjoying live music and the tropical scenery.


Gulfport Beach (Shore Boulevard, Gulfport, FL 33707) - Relax on the sandy shores of Gulfport Beach and soak up the warm Florida sun, while enjoying beautiful views of the Gulf of Mexico.

Clam Bayou Nature Park (south of 29th Ave South on Miriam Street) - Explore the serene trails of Clam Bayou Nature Park, where you can spot various bird species, kayak through mangrove-lined waterways, and immerse yourself in the natural beauty of the area.

Gulfport Tuesday Fresh Market (Beach Boulevard, Gulfport, FL 33707) - Indulge in a vibrant open-air market experience at Gulfport's Tuesday Fresh Market, featuring an array of local vendors offering fresh produce, artisanal crafts, tasty treats, and live music.

Gulfport Casino (5500 Shore Blvd S, Gulfport, FL 33707) - Dance the night away at the historic Gulfport Casino, a waterfront venue known for its lively dance floor, live music, and stunning views of Boca Ciega Bay.

Gulfport Art Walk (Beach Boulevard, Gulfport, FL 33707) - Immerse yourself in Gulfport's thriving arts scene by strolling through the monthly Art Walk, usually on the first Friday of the month. where local artists showcase their works in various mediums, galleries open their doors, and the streets come alive with creativity.

O'Maddy's Bar & Grille (5405 Shore Blvd S, Gulfport, FL 33707) - Enjoy a delicious meal and a lively atmosphere at O'Maddy's Bar & Grille, a popular waterfront eatery offering a diverse menu, craft beers, live entertainment, and stunning sunset views.

Gulfport History Museum (5301 28th Ave S, Gulfport, FL 33707) - Delve into the rich history of Gulfport at the Gulfport Historical Museum, featuring exhibits and artifacts that showcase the city's fascinating past and maritime heritage.

Boca Ciega Millennium Park (12410 74th Ave N, Seminole, FL 33772) - Just a short drive from Gulfport, explore the natural beauty of Boca Ciega Millennium Park, a sprawling green space with walking trails, picnic areas, a dog park, and stunning waterfront views along the Intracoastal Waterway.


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