St. Augustine Bars: Old City
The historic district between the Castillo de San Marcos and the Bridge of Lions: the pedestrian blocks of St. George Street, the brick lane of galleries on Aviles Street, and the bayfront along Avenida Menendez. The densest run of restaurants and bars in the city, many of them in buildings with a century or two behind them.
St. Augustine's oldest Irish pub by its own count, open since 1992 in an 1878 family home by the Old City Gate. Owner Kelli Meacham spent 16 years as a county deputy before buying it, the porch is where the regulars people-watch, and it goes 21 and over after 7 p.m.
A self-serve tap house and sports bar just south of the City Gate on St. George Street. Its Instagram bio says 13 TVs to watch your fav teams, and recent posts promote college football game days.
St. Augustine's only Irish gastropub by its own description, on Spanish Street since 2011 and open until 2 a.m. every night, with a late-night menu and a weekend brunch for late risers.
An outdoor amphitheater under what the park calls the city's second oldest live oak, just off the busiest block of St. George Street, with seating for more than 250. Shows are free unless noted and open to all ages, usually 7 to 10 p.m., and it is a Sing Out Loud Festival stage in September.
Comfort food and shrub-based cocktails on Aviles Street, the narrow cobblestone lane it calls the oldest street in the USA, in the space that used to be Cellar 6. It adds an optional surcharge that funds health, dental and vision insurance, maternity leave and paid time off for its staff, and it says so on its own site.
Three rooms in one building a block south of the fort: the Irish pub, Johnny's Oyster Bar upstairs with a deck over Matanzas Bay, and the Backyard's island bar. The house belonged to William Diskmuits, first president of First Florida National Bank, and the music runs daily.
An 1880s gristmill that became a bar in the 1950s, with live music every day and a treehouse-style room upstairs whose balcony hangs over St. George Street. The 2016 renovation turned up a forgotten water well and a two-foot gopher tortoise shell, and the 300-year-old pecky cypress went back on the walls.
A Prohibition-era gastropub on the site of the old Genovar Theater, with live music every night and what it calls the longest bar in the city, built from 400-year-old heart pine reclaimed from the original colonial structure. Speakeasy booths downstairs, a balcony over the stage upstairs.
A flower-filled courtyard and upstairs bay views make Saint a tempting Italian dinner spot. Explore the menu and seating choices, then book the table you want.
A fast casual seafood counter on St. George Street built around wild American shrimp, Minorcan chowder and a datil-buffalo shrimp, with a kids section on the menu. It shares the Colonial Quarter with the Colonial Oak Music Park, which is where its live music happens.
A cigar bar and listening room on the cobblestone stretch of Charlotte Street, locally owned for more than 23 years, with live music daily, hundreds of craft beers and a fire pit outside. Buy a draft before 7 p.m. and a hand-rolled cigar comes with it.
The martini bar of the Casablanca Inn, spilling out onto the front verandah over Matanzas Bay. Its own site says there is no live music right now, while Visit St. Augustine still lists Friday jazz, which is exactly the kind of mismatch this site exists to measure.
Open since 1945, owned by the Leonard family since 1961, and still pouring 365 days a year. Two merchant marine sailors shipped home the teak bar and the grinning idol behind it, its own history runs from Gamble Rogers to Jimmy Buffett, and the house drink arrives with its own thunder and lightning.