Gulfport

The Old Florida vibe of the restaurants and shops in this community hidden away on Tampa Bay makes it worth a day trip from nearby beach towns.

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Kayakers head out into Boca Ciega Bay along Williams Pier from Gulfport’s beachfront. There’s plenty to do onshore, as well. [Florida Beach Insider photo]
Pros
  • A dog friendly town.
  • Home to some of the region's best restaurants and an eclectic art scene.
  • Laid back, casual lifestyle. No frills!
Cons
  • There's not much of a beach.
  • The water quality is questionable.
  • Not enough to do beyond a day trip.

People don’t come to Gulfport for the beach. They come for the characters, the eclectic art scene and the food.

Between downtown St. Petersburg and St. Pete Beach, it’s a city that beats to its own drum, with a lively main street of bars, restaurants and local music, and a waterfront historic casino that still hosts weekly dance classes.

Incorporated in 1910 after a series of name changes (Disston City, Bonifacio, Veteran City), Gulfport offers an offbeat day trip or fun one-night stay for the foodie or outdoor adventurer who is cool with a “no frills” attitude.

The vibe isn’t quite as quiet as Cedar Key, and it’s not as lively as the Florida Keys, but Gulfport is as downright funky as both places.

Cruise through the brick-lined neighborhood streets and you’ll see “Keep Gulfport Weird” signs dangling from neon-colored mailboxes in front of charming Old Florida-style homes with wrap-around front porches. And watch out for the locals who cruise by on pirate-themed golf carts or motorcycles on Shore Boulevard on their way to karaoke at O’Maddy’s Pub.

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GETTING THERE

Tampa International Airport (TPA) is the main airport hub for the region over the Howard Frankland Bridge in Hillsborough County. All major airline carriers fly in and out of this regional and growing hub.

St. Pete-Clearwater International Airport (PIE) is physically closer to Gulfport in Pinellas County, but offers a select range of flights, mostly by discount airline Allegiant Air. That said, it’s a small and quick airport to navigate.

Gulfport is easy to get to via car from all major metro areas in Tampa Bay. It’s at the southern end of Pinellas County, but is less than a 15-minute drive from downtown St. Petersburg or St. Pete Beach. It’s a 40-minute drive from Clearwater Beach.

Beach Boulevard is the main road that leads into the city off 22nd Avenue South. Most of the city’s businesses are located on Beach Boulevard, which dead-ends into the town’s historic casino. Some waterfront restaurants extend out on Shore Boulevard, too.

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PARKING

Gulfport has ample free parking available. There is a free lot in front of the beach access on Shore Boulevard, and free spaces available along Shore and Beach boulevards. On the off chance that parking is hard to come by, visitors can parallel park on the neighborhood streets just a few blocks off the main commercial areas.

Gulfport also operates its own trolley, which visitors and residents can ride around the city for free. It operates every first Friday and third Saturday evening from 6 to 10 p.m. You can park at Wood Ibis Park, the Recreation Complex, the public library, the senior center or Chase Park and wave down the driver to get a ride. More information about the trolley is here.

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BEACH SCENE

Gulfport’s beach is small, but one big advantage is that there’s a playground right along the shoreline. [Florida Beach Insider photo]

Gulfport does have a public beach area on Boca Ciega Bay, which offers impressive views of the neighboring Tierra Verde neighborhood and the historic “Pink Palace,” the Don CeSar resort on St. Pete Beach. It’s a great spot to watch the sunset.

But the beach is small and pales in comparison to its better-known neighbors, like Pass-A-Grille and St. Pete Beach. Since Gulfport’s beach is on the bay and not the Gulf of Mexico, the water can be murky and the shoreline is often stuffed with seaweed.

Gulfport’s beach has suffered in recent years because of the city of St. Petersburg’s failing sewage system. Sewage has been pumped into Boca Ciega Bay, and while the water has been deemed safe to wade in, it’s really not recommended.

The beach is just steps off Shore Boulevard, which hosts a slew of restaurants and bars. The beach area hosts several local volleyball leagues and tournaments. Local yoga classes are sometimes take place in the mornings, too.

There is a public fishing pier at the east end of the beach which is popular with the locals. Sea trout, snook, amberjack and Spanish mackerel are the local catch.

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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.

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THINGS TO DO


Williams Pier in Gulfport is an ideal place to try to catch sea trout, snook, amberjack and Spanish mackerel. [Florida Beach Insider photo]

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.

Fun Unlimited boat rentals

Pontoon and deck boat rentals are available at the Gulfport Municipal Marina. You can reserve jet ski tours and charter boats here, too. (Mariner’s Cove Marina is primarily for locals to store their personal watercraft.)

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.

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.

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.

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.

Justine Griffin is a native Floridian with a lifelong love of horses. When she's not writing about health topics for the Tampa Bay Times, you'll find her exploring Florida's state parks aboard her Thoroughbred, Mikey.

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