Over 50 St. Augustine: 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.
Go early. It turns into a late-night spot later in the evening.
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.
Go early. It turns into a late-night spot later in the evening.
Lunch in the deep end of what was once the largest indoor swimming pool of Flagler's 1888 Alcazar Hotel, now the Lightner Museum. Classical guitar or piano plays from noon to three every day, museum admission is not required, and the cafe itself says reservations are highly recommended from October through March.
Live music some nights. Go before the band starts if you want to talk.
A Second Spanish Period family home, restored and opened as Casa Maya in 2015, now known for octopus, ceviche and seafood paella. The patio has its own stage with live music three or four nights a week, and the restaurant says up front that the upstairs group room has no elevator.
Live music some nights. Go before the band starts if you want to talk.
Named for Florida, the 27th state, and built around fish caught in Florida waters and delivered daily: snapper to sheepshead, mahi to triggerfish, depending on the boat. The local accent shows up in the Minorcan seafood chowder and the datil pepper ketchup.
Owners Mike Hyatt and Cindy Stangby cook local seafood, lamb and veal with international flavors, everything from scratch, behind a set of wooden doors on Hypolita Street. It has made OpenTable's Top 100 restaurants in America more than once, and its sister restaurant is Blackfly on Anastasia Island.
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.
This is a music venue. It is loud when a show is on.
The St. Augustine branch of the Columbia, the family group whose Tampa original has served since 1905 and bills itself as Florida's oldest restaurant. This one opened on St. George Street in 1983, and the rooms are the draw: hundreds of hand-painted tiles, a Spanish-style fountain, and private dining for groups of 10 to 200.
The dining room of the Casa Monica, which opened in 1888, was bought and renamed the Cordova by Henry Flagler four months later, and spent years as the county courthouse before it became a hotel again in 2000. The old Costa Brava relaunched here as a chophouse in November 2023, with a wine list holding a 2026 Wine Spectator Award of Excellence.
Old Florida home cooking on St. George Street for more than 35 years: gator tail, fried green tomatoes, shrimp and grits. The name honors the original Cracker cowboys, and the garden patio welcomes dogs, which the cafe says on its own site instead of leaving you to guess.
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.
Family-run Greek and Polish cooking, from pierogies to spinach pie and stuffed cabbage, named for its crisp sugar waffles. Its website is an under-construction page, and listings now put it at 212 Charlotte Street, reached through an Aviles Street alley, where older write-ups say 9 Aviles. Treat the address as unconfirmed.
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.
Go early. It turns into a late-night spot later in the evening.
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.
This is a music venue. It is loud when a show is on.
The St. Augustine member of the Jacksonville-area Mojo family, in the Old City since 2012, smoking across regional styles from Kansas City burnt ends to Carolina vinegar pork. Dogs are welcome on both patios, where the staff keeps water bowls ready, and plan on city parking because the lot is for staff.
Family-owned for 16 years: owner Adamo and his two sons cook from recipes handed down through the family and greet the tables themselves. It sits on Aviles Street, the brick pedestrian lane of galleries, and the room fills fast enough that Visit St. Augustine suggests arriving early on weekends.
A house with a longer resume than most of the city: Don Miguel Ysnardy built it around 1790, it served as one of St. Augustine's first hotels, and in 1961 it was moved to this spot on the bayfront. The O.C. White family has run it since 1992, with a garden patio, a balcony for the sunset over the bay, and live music in the evenings.
Live music some nights. Go before the band starts if you want to talk.
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.
Go early. It turns into a late-night spot later in the evening.
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.
This is a music venue. It is loud when a show is on.
A bakery under St. George Street's famous cedar tree, with a stone hearth oven and a separate smokehouse, turning out empanadas, picadillo and bread every day. Its own website has not been updated since 2013, so the address comes from Visit St. Augustine and Yelp, and those two disagree on hours. Do not plan around the posted hours until the bakery publishes a current schedule.
The only fully plant-based kitchen in this roster: a cafe and juice bar using organic, non-GMO and local ingredients where it can, with cashew cream cheese and carrot lox on the bagels. Founder Chef Forrest Masters came up through the Present Moment Cafe and the Ann Wigmore institute.
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.
This is a music venue. It is loud when a show is on.