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‘Everyone has a story about how they found Gulfport. Mostly, Gulfport finds you’

For such a small downtown village, Gulfport, Fla., has an impressive cluster of worthy restaurants and rollicking bars.
For such a small downtown village, Gulfport, Fla., has an impressive cluster of worthy restaurants and rollicking bars.Pamela Wright for The Boston Globe

GULFPORT, Fla. — The sun is setting across Boca Ciega Bay and we’re sitting outside at O’Maddy’s Bar & Grille, listening to live music and people-watching. It’s a fun, laid-back place, filled with folks of all ages, looks, and persuasions. There are dogs, and tattoos and torn shirts, and same-sex couples dancing in the street. There’s smoke in the air, and plenty of laughter, and a few alcohol-provoked scuffles. Later, after enjoying stiff drinks and delicious crab cakes, we notice a bearded, scruffy-looking man pulling up in a rainbow-colored golf cart to pick up a patron who clearly needs help getting home. Uber, Gulfport-style.

The residents of Gulfport are the first to admit that their lively little town is quirky, even a bit weird. Funky. Eclectic. Freewheeling.

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“A lot of people tell us that Gulfport is like Key West in the ’70s,” says Scott Linde, president of the Gulfport Merchant Chamber. “So far, we’ve managed to keep it that way.”

Gulfport, Fla., has been a bolt-hole for people who want to live in don’t-judge-me ease, and who eschew the trappings of too much progress.
Gulfport, Fla., has been a bolt-hole for people who want to live in don’t-judge-me ease, and who eschew the trappings of too much progress.Pamela Wright for the Boston Globe (custom credit)/Pamela Wright

Located across the bay from St. Pete Beach, this small waterfront village with an Old Florida, offbeat vibe, has been a bolt-hole for people who want to live in don’t-judge-me ease, and who eschew the trappings of too much progress. The result is unconventional and captivating: a flashback, beachfront downtown that stretches only a few blocks but is packed with restaurants, small shops, bars, and colorful characters.

“Everyone has a story about how they found Gulfport,” Barb Banno, owner of Stella’s restaurant, says. “Mostly, Gulfport finds you.”

Years ago, a friend invited Banno to attend a Gulfport Friday Night Art Walk, and she found home. Even though she’d never worked in a restaurant, she opened Stella’s. “I knew I wanted to be part of this community,” she says. “And I love going out to breakfast.”

Today, Stella’s (www.stellasingulfport.com) is ranked as one of the top restaurants in Pinellas County, serving hearty, homestyle breakfast and lunch. During nice weather, crowds spill out onto the dog-friendly patio, enjoying Southern shrimp and grits, banana bread French toast, and the house-made corned beef hash. For lunch, start with the cheddar-filled pierogis or black bean cakes, or go straight for the restaurant’s famous fried green tomato BLT or the monster-size Cuban sandwich.

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For such a small downtown village, Gulfport has an impressive cluster of worthy restaurants and rollicking bars. The family-owned O’Maddy’s Bar & Grille (www.omaddys.com) has been around for three decades and is a local favorite, with outdoor seating, live entertainment, a friendly staff, and decent food. We thought their famous RBK with roast beef and horseradish sauce on a kimmelweck roll and the Gulf of Mexico grouper sandwich were both tasty. Pia’s Trattoria (www.piastrattoria.com) is a sweet Italian restaurant filled with checkered tablecloths and live plants, serving classics like the hearty spaghetti Bolognese, and osso bucco with saffron risotto. We liked the gyros and spinach pie at Neptune Grill (www.neptunegrillgulfport.com); they also have daily specials like $3 Monday margaritas, and live music on the weekends. Isabelle’s is one of the finer dining spots in the village (www.historicpeninsulainn.com/dining-at-isabelles#). Grab a table on the spacious veranda, surrounded by lush plantings, to enjoy classic American dishes with a little Southern flourish, like the low-country shrimp and grits, lamb T-bones, and Creole chicken pasta. (There’s inside dining, too, but the porch is lovelier.)

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If you’re looking for a quick jolt, pop into the GulfPerk Coffee Bar (www.facebook.com/gulfperkcoffeebar) and then pick up something sweet at A Friend Who Bakes (www.facebook.com/afriendwhobakes).

Hanging around Gulfport is pleasure enough, poking into the handful of trinket shops and galleries. There’s interesting people- and dog-watching, a pretty bayside beach and park, a fishing pier, two marinas, and the historic 1930s Casino Ballroom, which commands center stage on the waterfront and hosts concerts, dance lessons, and special events. On the first Friday and third Saturday of every month, the city also hosts Art Walk, showcasing the work of local artists, and drawing in crowds of visitors.

One day we joined a guided kayak tour of Clam Bayou, a tidal estuary thick with mangrove forests and mudflats. “It’s a nice little corner of Gulfport,” says Kurt Zuelsdorf, owner of Kayak Nature Adventures (www.kayaknature.com). Shaped like a horseshoe, the 180-or-so-acre estuary opens into Boca Ciega Bay and beyond to the Gulf of Mexico. Fish jumped around us and birds flittered overhead as we slowly paddled through the murky waters, ducking under branches and squeezing through mangrove-carved tunnels. The estuary wasn’t always this peaceful. At one time, it was filled with massive heaps of garbage. Zuelsdorf, recipient of St. Pete Audubon’s “Conservationist of the Year” award, has worked for more than 11 years with hundreds of volunteers to help clean it up, working in small boats and kayaks to pull out the debris. “Anything you’d find in a Walmart, we found out here,” Zuelsdorf says. “We stopped counting at 350 shopping carts and 400 tires.” They also found a blow-up sex doll that they nicknamed Bayou Betty. “We hid it for the teenagers to find when they were out here,” he says.

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Hanging around Gulfport is pleasure enough, poking into the handful of trinket shops and galleries.
Hanging around Gulfport is pleasure enough, poking into the handful of trinket shops and galleries.Pamela Wright for the Boston Globe (custom credit)/Pamela Wright

On our final day, we met with Cathy Salustri, president of the Gulfport Historical Society, (www.gulfporthistoricalsociety.org), who leads tours in the city. Salustri told us that she ended up in Gulfport not by design but by serendipity. A friend invited her, and she too found home. “A lot of us didn’t plan to move here,” she says. “A car breaks down; someone makes a wrong turn. But we end up staying. It does this thing to people and you just have to be here.”

Salustri leashed her sweet little hot dog of a pup and we walked through neighborhoods of brightly-painted cottages, Spanish-style haciendas, and Sears and Roebuck houses, as she told us about Gulfport’s somewhat nefarious past. The city was founded by Confederate sympathizers who fled Key West when the Union took over, and was later a center for mullet fishing. When the mullet stocks dwindled, the fishermen looked for a new currency. “Square mullets,” Salustri said with a smile. Drugs.

“We were flying under the radar, forgotten,” she said, “Everyone was looking at Key West and Miami.”

The drug trade has cleaned up, along with the city. “When I told my mom that I was moving to Gulfport, she was horrified,” Salustri says. “Now, she loves the place!”

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You can pick up something sweet at A Friend Who Bakes in Gulfport, Fla.
You can pick up something sweet at A Friend Who Bakes in Gulfport, Fla.Pamela Wright for the Boston Globe (custom credit)/Pamela Wright

Later that evening we sat at Caddy’s, another popular beachfront bar (www.caddys.com/caddys-gulfport), noshing grouper bites and eavesdropping on the local gossip. Who was going to be Gulfport’s first-ever pet mayor? There were now 12 furry, four-legged candidates on the ballot. Well, 13 if you count the two cats running on the same ticket.

If you go: There are two hotels in town, and lots of home rentals. The Sea Breeze Manor Inn, a quaint, two-story B&B across the street from the bay and within easy walking distance to restaurants and shops, has six spacious suites, with private baths (www.facebook.com/seabreezemanorinn). The atmosphere is cozy and relaxed.

You can’t miss the 1905 Historic Peninsula Inn (www.historicpeninsulainn.com), a sprawling, three-story, bright yellow building in the center of town. It’s surrounded by lush plants and boasts a beautiful front veranda, home to Isabelle’s restaurant, but the rooms could use some updating; some of the furnishings are getting shabby.

For more information, visit www.visitstpeteclearwater.com/communities/gulfport.


Diane Bair and Pamela Wright can be reached at bairwright@gmail.com