Nightlife in Gulfport

Select Local Merchants

Woody's Waterfront Cafe, built on an inlet off the Gulf of Mexico, regales guests with vintage 1960's beach-bar vibes and scenic views, shimmying up a menu of casual American fare and ice-cold drinks. Commence the evening with one of Woody's basket cases, which nestle a bushel's worth of plain or spicy fries next to bite-sized morsels of chicken, shrimp, clams, or wings ($8.75–$12.50). Otherwise, the burgers—half-pound patties of grilled chuck cooked to preference—make for hearty handheld eats and surprisingly accurate discuses ($7/50–$8.45), and the cheese-topped surfin' steak sandwich snares shaved slices of grilled sirloin and veggies within the soft embrace of a bun ($8.25). Woody's chefs also sizzle up mahi-mahi steak, which comes blackened, grilled, or fried, and plated with a choice of two sides ($12.95). At the full bar, bartenders sling draft and bottled beer, as well as a bevy of frozen mixed drinks that include mudslides authentically prepared with the mire from Mt. Oreo's historic avalanche.

7308 Sunset Way
St Pete Beach,
FL
US

Emilio's is one of St. Petersburg's newest additions, offering denizens a sampling of fine coffee, pastries, paninis, burgers, and more. Light the flare on flavor landing strips with Emilio's bottomless cup of blend roasted coffee ($1.50) and the morning-making berry parfait similar to earth's interior of layered crunchy granola and berries atop Greek yogurt and honey ($4.99). The baguette blanche treats midday diners to a medley of savories masked in the makeup of stacked turkey, grilled mushrooms, caramelized onions, cream cheese, and pesto ($7.99), and the roasted red-pepper and goat-cheese panini adds a dash of zest with fresh basil, red onions, and a zigzag of balsamic vinegar ($9.99). Unlike stuffed animals, stuffed burgers won't fight back when bit and can be filled with a variety of tasties such as applewood smoked bacon, sundried tomatoes, pesto, and brie ($10.99). Pair meals with one of the restaurant's many wines or craft beers.

437 Central Ave
Saint Petersburg,
FL
US

Max & Sam's Bar & Grill carries on a classic neighborhood-chophouse tradition with hand-cut steaks and seafood served within dark-wood-paneled walls built in 1924 and brushed against by the likes of Al Capone, Marilyn Monroe, and Joe DiMaggio. Under the gaze of jazz-age crooners swirled onto framed canvases, soaking up aromatic inspiration for their next musical meditation on cheese grits, the five-course meal kicks off its culinary set list with parmesan-crusted beef tips or calamari. Bowls of the chef's french-onion or soup du jour, depending on whether jour is in season, set the scene for a simple house salad of mixed greens and veggies.

1700 Park St N
Saint Petersburg,
FL
US

Three Florida-based acts will entertain crowds with a mix of R & B, Southern rock, and funk during "Beach Chair Blues Night," held in Jannus Live's well-appointed outdoor courtyard. Sitting in their own beach chairs, attendees can groove to the soulful sounds of the headliners, the Mike Kach Group, whose eponymous singer and keyboardist tickles ivories on piano, organ, and stray elephant. Local guitarist and vocalist Jimmy Griswold serves as a special guest for the evening, and Southern rock opening act The Standback Band will perform with a recruited roster of fellow Bay Area blues musicians.

16 2nd St N
Saint Petersburg,
FL
US

Owned in part by former Heat star Matt Geiger, Courtside Grille reflects its dedication to sports with its distinctive logo: four sleek, intersecting streaks forming a stylized basketball. The crest can be found in every area of the restaurant, whether glowing white against the brick walls, or hanging over the bar as a light fixture. In the dining room, guests share piping-hot flatbreads and bites of burgers, pork chops, or Caribbean-style glazed salmon while betting their antique spoon collections on sports games broadcast on the 24 TVs.

110 Fountain Pkwy N
Saint Petersburg,
FL
US

Crum's Bar and Grill regales visitors with hearty feasts of inventive pub cuisine paired with plenty of craft beer and live entertainment. Guests belly up to the bar to sample 52 lagers, ciders, stouts, and IPAs on draft, or commune with the spirits of our sandwich-hunting ancestors while watching juicy burgers cook over an open fire. Regularly scheduled entertainment—from Thursday karaoke operas to live bands on weekends—adds a musical touch to meals, and dart boards and Xboxes release reserves of competitive energy.

2924 5th Ave N
Saint Petersburg,
FL
US