Undiscovered Florida

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Looking for 'Old Florida' this quirky waterfront art village is it.

There is something for everyone in Gulfport, but if you didn’t know it was here, you might never find it. Five minutes off of I-275, head east on 22nd Avenue South, and follow Beach Boulevard to the water. Or come to the pier by boat, with the green Historic Casino and Ballroom as your landmark. Gulfport sits on the southern tip of St. Petersburg, tucked away from traffic and commotion, on the edge of beautiful Boca Ciega Bay.

Residents and visitors compare Gulfport to “the old Key West,” before cruise ships and booming tourism. Both small artist towns evolved from old Florida fisherman villages, yet Gulfport retains an untainted, classic character. Think cobblestone streets, 1920 bungalow cottages of different colors, small-town laid-back friendliness, and enough local attractions to enjoy a day, a weekend, or longer in paradise. Contrary to usual small towns, the residents are open-minded and welcoming of everyone.

You’ll eat like a tourist and feel like a local. There are ten restaurants and bars within walking distance, five of which have a waterfront view. Enjoy Pia’s Italian cuisine under an authentic tiki hut, or La Cote Basque’s French menu. Stop by H.T. Kane’s for a beer and beach food, or settle on the outside deck of Cahill’s Beachside for delectable seafood specials. Featured in Southern Living, Habana Café offers authentic Cuban cuisine. Every year Tampa Bay awards Backfin Blue with the best crab cakes in the area. Most of the restaurants offer outdoor seating and you’ll be surprised how many provide live music.

Have breakfast at Sal’s. Watch the sunset on Aqua Bella’s upper deck. Dine at the Historic Peninsula Inn and Spa’s Six Tables Restaurant. Go to Gulfport On The Rocks and see where Jimi Hendrix used to play, a rumored hangout of Jack Kerouac. O’Maddy’s is a popular late-night hangout with a live DJ and karaoke every night. Connecting is their restaurant, which serves lunch during the day and has a quiet lounge atmosphere after dark. In between, be sure to stroll down the pier and look out over the water. Stay the night at Lori Rosso’s Bed and Breakfast, for a pampering and personal tour guide, or the Historic Peninsula Inn and Spa with an indoor/outdoor restaurant and courtyard.

Aside from food and fun, Gulfport’s true uniqueness lies in its collection of local artists. Historic with a bohemian flare, downtown consists of art boutiques, clothing stores, and The Art Village, complete with a courtyard coffee shop, where you can sometimes catch live entertainment. There is an old antique and general store, The Beach Bazaar, with a post office in the back, and The Small Adventures Bookstore in case you need something to read for the ride home.

Every first Friday and third Saturday of the month the community holds “Art Walk” on Beach Boulevard. The stores stay open late. Local artisans and musicians line the street to sell, and showcase their talent. From paintings to jewelry, and drums to stone candles, Art Walk is a must, a great place to buy gifts or souvenirs. The community also hosts larger annual festivals like Gecko Fest (September), Taste of Gulfport (November), Spring Fest (April), The Pink Flamingo Homes Tour, and downtown holiday parades with “the best Fourth of July display on the beach.”     

There are also some hidden aspects of Gulfport. The Historic Casino Ballroom invites you to dance to live music, five nights a week. $7 gets you a half-hour lesson and a night of swing dance; salsa, line dance, or you can brush up on your ballroom skills. If you’re into watching plays, The Catherine Hickman Theater hosts off-Broadway productions and regular performances by the local theater group, The Gulfport Community Players. Every Friday and Saturday night and during special events, Gulfport gives free trolley rides. Take a tour of the historic town, or use the trolley to help you with parking.    

Whatever your palate, entertainment, or atmospheric preference, Gulfport is a place to experience. Charming and secluded, the citizens have managed to preserve an old Florida classic community.

"Gulfport is truly a unique and special place,” says Greg Stemm, executive director of the Gulfport Chamber of Commerce. “Our remarkably diverse local population, and amazing array of artists, exceptional restaurants, lively beach pubs, a full state of year round events and charming cottage homes blend together into a welcoming bohemian atmosphere. We’ve managed to retain that elusive feeling of small town character that has all but disappeared in much of Florida. We welcome visitors of all kinds with our homespun friendliness too. Come see us.”

For a small beach town, there are enough happenings to keep you busy for quite some time. Or if you’re looking for a quiet getaway, Gulfport is the perfect place to relax on the beach and enjoy the tropical birds or the dolphins frolicking in the bay. Once you visit, though, you might not want to leave. I asked the first person I met here how long he’d been in Gulfport. “Well,” he said, “I stopped here to have a beer on my way back to Georgia in ’88…and I never left.”

For more information on Gulfport or a schedule of the free trolley rides, contact the Chamber of Commerce, Bank of America Building, 2808 58th St. S, Gulfport, Florida, 33707. (727)-344-3711.

Whitney Bell

(727)-455-4683

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