Order off-menu at Wildwood BBQ and Burger, a satellite of Gramercy Park’s popular ’cue pit, where secret standouts include a bacon trio ($5.95), buttery kernel-studded skillet cornbread ($4.50), and the Pitmaster Combo ($34.95) with three kinds of ribs, sliced brisket, pulled pork, and a half chicken. Skip the beer and peruse the excellent wine list, which lists a full-bodied 2007 Hangtime Pinot Noir ($36).
Dine among Pinellas County’s young, upwardly mobile set at Cassis, downtown’s new brasserie outfitted with leather booths, tiled floors, and tables that sprawl out onto the sunny street corner. Tender scallops with smashed peas ($25) and juicy duck confit ($22) are tasty options, but no trip to Florida would be complete without an early bird special—here it’s a flexible three-course menu for $20.11 available from 4 to 7 p.m.
Nurse a home-brewed Square Dancing IPA ($5) and munch on wild mahimahi tacos ($15) and sugarcane shrimp skewers ($15) at Peg's Cantina, a woodsy, relaxed bungalow surrounded by sand pines and native Florida palms. The sprawling cedar deck is a great place to watch time pass slowly in the overlooked Gulfport neighborhood.