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Secret Florida – Part Four, Gulfport

By Susan & Simon Veness

When you’re ready to go beyond the obvious places in the Sunshine State, there are a wealth of small towns and other ‘secret’ destinations that the locals know about but which are often a mystery to visitors. This series is dedicated to revealing these hidden gems.

The Gulfport municipal website insists it has “no chain stores, no parking meters, just small-town warmth,” and this is definitely an occasion when you can take them at their word.

Because this funky little community – ‘town’ is really too big a term for it; ‘village’ would be too small – is a genuine hive of down-home hospitality and charm that sits happily alongside the more urbane appeal of nearby St Petersburg and the many beach resorts along the Gulf Coast.

Just to start with, its population numbers barely 13,000 and it covers fewer than four square miles (one of those being its water extent into Boca Ciega Bay). It is most assuredly small-town America, and yet it has a big-hearted feel, a sense of inclusivity and genuine welcome for all-comers.

There is also a distinctly artsy-crafty vibe, which becomes understandable when you learn the town’s recent history. Lori Russo, landlady of the Sea Breeze Manor Inn told us: “This is very much a unique neighbourhood. It dates back to the 1980s, when there was a lesbian art community that moved in and helped re-establish the town. They were so successful they ultimately priced themselves out of business when rents went up, but some managed to stay and it all added to the diversity. It’s an amazingly mixed and welcoming community.”

And therein lies Gulfport’s secret, a sleepy seaside town, mixed with a new-age arts commune amid overtones of pre-tourism Key West. The overall effect is akin to a Bohemia-on-Sea of beguiling qualities, comfortably at odds with the high-rise resorts that sprawl along much of the coast.

Local novelist Sam Black added: “This is just a quaint, old-fashioned community. Nothing much has changed here in 50 years. We kind of like it that way.”

Except that would be to completely undersell its attraction as a real Florida gem, somewhere original and exciting for visitors to discover.


It would be understandable if Gulfport had an identity complex. It was originally founded as Disston City in 1884, but soon changed to Bonifacio after a naming conflict with another town in the county. It became Veteran City in 1890 before finally settling on its current title in 1910.

Getting to Gulfport

This possibly isn’t the easiest place in the state to find, and you will need a hire car to get here. Its tucked-away location is part of its allure, though. Situated on the intracoastal waterway between the mainland and the barrier islands of St Pete Beach and Treasure Island, it is less than six miles from St Petersburg and enjoys the benefits of being under that city’s urban umbrella.

From Tampa, take motorway I-295 south to Exit 19, just past St Petersburg. Head due west on 22nd Avenue South for just over a mile, then turn left at the crossroads with 49th Street South and go south until the road reaches a T-junction with 31st Avenue South, where you turn right and cruise into the main downtown area.

Casino Pier gulfport

So, what’s In Gulfport?

Driving in along 31st Avenue, it should be immediately clear that you’ve ‘arrived’ as you hit the junction with Beach Boulevard. This is Gulfport’s ‘Main Street,’ and runs for about 500 yards in all, ending at the seafront and Shore Boulevard.

Here you’ll find the town’s pretty waterfront, with its own sandy beach, recreation park, the iconic Casino Ballroom, and the Bert and Walter Williams Pier, which extends 500ft into the bay and usually sees the local fishermen out in force. The Ballroom is something of a local institution, too, with dancing five nights a week and people coming from as far away as Tampa to trip the light fantastic.

Shore Boulevard is also lined with an array of attractive bars and restaurants, as well as a handful of striking Inns and bed-and-breakfast options, including the highly recommended Sea Breeze Manor Inn, The Toasting Mermaid (yes, really!) and Beach RelaxMore.

Drive back along 31st Avenue and you’ll discover the Municipal Marina, where you’ll find Fat Cat Fishing Charters and Fun Unlimited boat rentals for a day exploring the local waterways. Also here is Clam Bayou Nature Park, a 10-acre estuarine preserve with hiking and boardwalk trails, observation deck and kayak launch. It provides a habitat and food for a variety of wildlife, notably fiddler crabs, clams, wading birds, raccoons, dolphins and manatees.

As a fine example of a small-scale seaside vista, it is hard to beat, while it is all immensely walkable. You can happily park up and get to just about anywhere on foot.

IMG 9722 gulfport

Best shopping in Gulfport

This is arguably where the town comes into its own, with an all-original line-up of shops, boutiques and galleries along the length of Beach Boulevard that truly lives up to the boast of “no chain stores.”

Instead of the big-name identikit brands, you’ll discover a wealth of one-off outlets that all have something different and distinctive to offer. Visit the likes of Gulfport Beach Bazaar, Domain Home Accessories, August Vernon Studios, Bo Tiki and the Village Courtyard for a wide variety of gifts, art and home décor, while Reef Dog is the place to shop if you have pets.

Every Tuesday sees the open-air Gulfport Fresh Market on the Boulevard from 9am to 2 or 3pm, with some 70 vendors offering everything from fresh fruit to jewellery and herbal therapy. It’s a one-of-a-kind mixture and well worth taking in.

Another must-try experience if you’re in town at the right time is the signature Gulfport Art Walk, an outdoor ‘art gallery’ of various artists’ wares and creations, held every first Friday and third Saturday of the month from 6-10pm. This is an event that brings the locals out to play, and it really shouldn’t be missed.

Gulfport restaurant

Best restaurants in Gulfport

Finding a good meal here is definitely not difficult. From lively, tropical-tinged bars to fine dining restaurants, the town has an astonishing variety on offer, and you will probably want to try as many as possible.

Seafood is firmly to the fore, and is a real speciality at places such as Backfin Blue Café, Neptune Grill and waterfront hot-spot Caddy’s, with its live music each evening and panoramic views from the top floor.

Fortunato’s is the place to go for good Italian cuisine, along with Pia’s Trattoria (try their calamari, followed by the shrimp scampi), and excellent Cuban fare is the order of the day at Habana Café, with its elegant décor and signature Lechon Asado (roast pork). Stellas’s provides classic Southern food – and killer Bloody Marys! – and, just out of the downtown area, Smokin’ J’s Real Texas BBQ is an exercise in fabulous barbecue offerings.

The veggie/vegan crowd are not forgotten, either, with some highly tempting dishes at Golden Dinosaurs Vegan Deli, while, for a tea or coffee break, GulfPerk Coffee Bar is the ideal place to sit and enjoy the view from their patio.

The bar scene is equally impressive, with a host of fun, lively venues for a drink or three as the sun goes down across the bay. In particular, we like the colourful scene at O’Maddy’s Bar and Grille, Little Tommie’s Tiki and the ramshackle, Key West style of Salty’s.

Finally, the historic, colonial-tinged Peninsula Inn is an attraction in its own right, as well as a good place to stay or just a stop for dinner at Isabelle’s restaurant (4-9pm; from 10.30am on Sunday; closed Monday). The cosy dining room features an Old Florida vibe yet a modern, seafood-orientated menu, including great crab cakes, scallops and seafood paella.

Gulfport Dining

And that is Gulfport in all its glory, an original, happening, distinctly offbeat town that definitely marches to the beat of its own drum but is very happy for visitors to drop by. We highly recommend that you do.

Susan & Simon Veness are the UK’s leading experts on Florida, having written about it for more than 25 years and sold more than half a million copies of their books about Orlando, Disney and the Sunshine State.

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