Things to do
Clam Bayou Nature Preserve: At the very east end of the city limits, just past the marina, is this preserve overseen by the St. Petersburg parks department. There are walking trails and public docks that offer views of local wildlife and mangrove estuaries. Clam Bayou also has a kayak launch.
Gulfport Casino Ballroom: Gulfport has had a casino on its waterfront since the town was incorporated, although it has traditionally been used as a meeting space instead of a gambling venue. The current building dates to the 1930s and is home to weekly dance nights throughout the week. The city has been working overtime marketing it as a wedding and meeting venue.
Williams Pier: This walkway allows visitors to walk more than 500 feet into Boca Ciega Bay, and is free to use. Fishing and cast-netting from the pier is encouraged with an available fish-cleaning table.
Places to eat and drink
O’Maddy’s Bar & Grille: A Gulfport staple. Located in front of the pier on Shore Boulevard, this dive bar has photos hanging on its walls of when hurricanes closed up every shop in Gulfport … except O’Maddy’s. The dingy look of the loud bar is deceiving: O’Maddy’s has an impressive chef on staff and offers high-quality gourmet food. Go early to avoid the crowds.
Stella’s: A southern-inspired breakfast and lunch diner on Beach Boulevard. It offers some of the best brunch in all of St. Petersburg. It’s cheap, too. Bring your dogs, the sidewalk seating is pet friendly.
Pia’s Trattoria: A beautiful southern-inspired Italian restaurant in an old home-turned restaurant. It’s a gorgeous place to eat and perfect for a date night. Come hungry: the portions are large and the wine is good.
Manatees On The Bay: This fun, lively tavern offers weekly bar games, like trivia, and is a hot spot for locals who play in the nearby volleyball leagues. As advertised, the rooftop bar here does indeed overlook the bay.
Where to stay
Peninsula Inn: This historic hotel right in the middle of everything on Beach Boulevard opened in 1905. The 40-room hotel served visitors who wanted to swim and fish in Boca Ciega Bay. After World War II, the hotel was turned into a hospital to treat war veterans. It was a nursing home and retirement home for many years, before being abandoned and falling into disrepair. It was bought in the 1999 and reopened in 2002 as a historic boutique hotel. It houses Isabelle's, a gourmet restaurant with a beautiful outdoor dining patio.
Beach Relaxmore: Instead of just one house, this is three — three different cottages are available for your stay. There are various sleeping options, so this is a good choice for larger families or groups who are meeting in Gulfport. You can bring a dog, but no cats.
Sea Breeze Manor Inn: A bed and breakfast right on Shore Boulevard, enjoy the Sea Breeze's namesake currents on a big front porch. This Tudor dates back to 1923, and was a private residence until a couple renovated it in 1996, and sold it to the current owner in 2002. Each of the six rooms has either a private balcony or patio.
Gecko Fest: The August festival, the largest event in Gulfport every year, is a way to celebrate the end of summer and pay homage to the city’s favorite and unofficial mascot, the gecko. Residents come decked out in reptile attire. The festival shuts down Beach Boulevard for a day to line the street with vendors, carnival games, shows and live music. In addition to the one-day festival, GeckoFest hosts an annual “Gecko Ball” at the casino during the week leading up to the festival, and a one-night-only Gulfport pub crawl.
Gulfport Springfest: Every April the city’s Clymer Park turns into an “enchanted village” with fairies and art, not unlike a Renaissance Festival, for one weekend only. This family friendly event has food, drinks and lots of shopping.
BoTiki: This is one of the largest and one of the most unique boutiques in downtown Gulfport. It offers an array of jewelry and clothing, and some home decor items.
The Gulfport Beach Bazaar: A wide area of antiques, unique beach home decor, clothing and more is up for grabs. In the true spirit of Gulfport, it doubles as the local U.S. Post Office, too.
Reef Dog Gifts & Grooming: If you’re a pet person, there are plenty of goodies here to bring home to your fur pal. There’s also a DIY dog wash on site.
Tips from townies
Don't dress up. This is a shorts and flip-flops kind of town. Come for brunch or the afternoon and enjoy all the sights, food and drinks Gulfport has to offer. Take an Uber from your hotel in St. Pete or St. Pete Beach, or bike over if you're up for it.