Ann O'Malley's Irish Pub & Deli

Old City · irish, deli

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.

Barley Republic

Old City · $$ · irish, gastropub

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.

Colonial Oak Music Park

Old City

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.

Meehan's Irish Pub & Seafood House

Old City · irish, seafood

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.

Milltop Tavern & Listening Room

Old City

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.

Prohibition Kitchen

Old City · gastropub

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.

Stogies Jazz Club & Listening Room

Old City

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.

Tradewinds Tropical Lounge

Old City

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.

Real People
Local Love
All Welcome
Extend Your Visibility

Find your next favorite spot

Get BellyUp! finds for your city and the things you love.

What do you love?