St. Augustine Bars: Uptown
San Marco Avenue north of the City Gate, where the foot traffic thins out and the Victorian houses take over, running up past the Fountain of Youth to the roundabout at the Vilano Bridge.
Boat Drinks
A tropical cocktail and oyster bar that outgrew St. George Street and moved in 2025 to a bigger room on San Marco Avenue with its own parking lot. It claims Florida's most expansive selection of high-end rums, and promises the only thing frozen is the drinks.
Cortesse's Bistro & Flamingo Room Piano Bar
A 1920 building at the Vilano Bridge roundabout with a Mediterranean kitchen that grows its own herbs and buys from local farms and fish markets. The Flamingo Room has live piano seven nights a week, and the courtyard does al fresco among tropical plants and fountains.