STAYCATION Gulfport
Gulfport is St. Pete’s secret
Somewhere between the Sunshine Skyway Bridge and Tropicana Field, there’s a small but cool waterfront community that not only isn’t on the Gulf of Mexico, but it’s never even made most Floridians’ radar. Put it on yours. Tiny Gulfport’s palm-lined streets, chock-a-block with vintage cottages, lead to a surprisingly adorable downtown. Best of all, Gulfport is pedestrian heaven AND pet friendly. Grab your pup and point the car north.
The first of your surprises (after, “Hey, why didn’t we know about THIS before?”) is the massive retro-looking waterfront building that serves as Gulfport’s social hub and dance hall— the Gulfport Casino and Ballroom. In 1906, a trolley line coming from St. Pete connected city passengers at this spot to boats that would carry them across the water to popular Pass-A-Grille Beach. Today Gulfport’s landmark casino, sans gambling, still stands, serving as the community hub. Look southwest from its massive dock and you won’t even have to squint to spy the historic Don CeSar hotel in all its pink glory out on the horizon.
Gulfport’s tiny post office is tucked inside the 20- vendor Gulfport Beach Bazaar, giving visitors a warm and fuzzy time-warp feeling. But little Gulfport—sweet and unabashedly quirky—has been getting better every year, and now has more than enough to hold your attention.
Downtown’s commercial district stretches for several blocks, all of which invite exploration on foot or by bicycle. Laid-back to the extreme, locals congregate in downtown bars, wearing the Gulfport uniform of tees and flip-flops. It’s a happy, small-town vibe.
Start your day over a crabmeat omelet or pumpkin French toast at Stella’s; sit indoors or out. O’Maddy’s Bar & Grille is a lively open-air scene with music, lots of sports on its many TVs and consistently good food (its lobster BLT is a hit). Head to Backfin Blue Cafe, another longtime favorite of both locals and visitors, for crab cakes.
Downtown’s Tiki Bar & Grill is a good bet for tapas and sangria. For dinner, locals love Pia’s Trattoria—by most accounts the best restaurant in Gulfport—for its authentic Italian food. Pia’s lasagna comes to the table on a cast iron plate to keep it hot.
There are some private rental homes in walking distance of everything. Downtown’s historic Peninsula Inn is where most couples find themselves checking in for a weekend or longer. With only 12 suites, the pet-friendly Peninsula has a large, lush patio, clubby dark-wood bar and a lovely veranda for dining. If
waterfront lodging is a must, check out the Toasting Mermaid bed and breakfast, a refurbished 1923 compound directly across the street from Boca Ciega Bay.
Pop into Paw Paw’s Pet Boutique with your four-footed friends, or treat yourself to some chic, beachy jewelry or clothing at BoTiki. The Boulevard Shoppe and Garden brings smiles with its vintage décor, antiques, unusual collectibles and working tea room. Stella’s Sundries Swag & Scullery (next to Stella’s restaurant) is a great stop for gifts. A handful of galleries are also scattered up and down Beach Boulevard.
Paddlers depart from Kayak Nature Adventures in the Clam Bayou Nature Park just east of the city marina. Any time is a good time to check out the boats on the shorter pier next to the Gulfport Casino. You can also catch some angler action on the longer pier across from O’Maddy’s. Early mornings are memorable here, as first light splashes pink hues above Boca Ciega Bay.
Gulfport’s unpretentious vibe and walkability tend to slow down its visitors. Should you develop an itch to explore farther afield, however, suitably quirky day-tripping options include renowned Haslam’s Book Store (2025 Central Ave., St. Pete, 727-822-8616); the Salvador Dali Museum (1 Dali Blvd., 727-823-3767); or, on Tuesday, Thursday or Friday evening, the St. Petersburg Shuffleboard Club, which happens to be the world’s largest (559 Mirror Lake Dr. N., 727-822-2083).