Where to Find Free Live Music in St. Augustine

From restaurants, bars and unexpected hidden venue gems, the Ancient City's live music scene sounds offers countless opportunities for a fun (and inexpensive) day or night entertainment.

Few cities are better for a day trip from Orlando, in fact, if you're looking for a step-by-step itinerary for a few hours in St. A – we've got it! From romantic unique bars to a few whole-in-the-wall spots, here’s where to find free live music in St. Augustine.

Free Live Music in St. Augustine

Ann O’Malleys

23 Orange St., St. Augustine, FL 32084

This pub offers live music Fridays and Saturdays with trivia and open mic nights, as well throughout the week. Don’t miss their naughty bingo on Sundays or their great selection of sandwiches and hot dogs.

The Cellar Upstairs at San Sebastian Winery

157 King St., St. Augustine, FL 32084

Tapping on to the delish freebie perks of San Sebastian Winery, find free live music in St. Augustine's favorite rooftop wine bar. With daytime schedules begging for a lingering afternoon lunch or brunch, jazzy music and nibbles are available for patrons of The Cellar Upstairs.

Colonial Oak Music Park

21 St. George St., St. Augustine, FL 32084

Talk about value! This incredible open-air venue, right off of St. George Street near the fort, is a stellar place to spend an evening with friends or loved ones. With a variety of sets, from country jams to rock n’ roll and more, visitors need only pay for drinks.

With free and pay-what-you-will shows, this is a slam dunk for a budget night out on the town. Enjoy the twinkle and lantern lightning from the tree branches above for a romantic and/or fun-filled evening.

Plus, for an added bonus, note that ALL ages are welcome. The more the merrier, so mark your calendars now for upcoming shows and festivals that amp up free live music in St. Augustine.

Concerts in the Plaza

Plaza de la Constitución, 170 St. George St., St. Augustine, FL 32084

Check back with us soon for details on the summer 2024 offerings for Concerts in the Plaza, an annual free concert series in the heart of St. Augustine. Hear Americana, country, bluegrass, rock and so much more at these lovely community events. The series is conducted in the charming Plaza de La Constitucion on Thursday evenings.

First Friday Art Walk Concert Series

38 Cathedral Pl., St. Augustine, FL 32084

Not a bar or lounge, but a great place to enjoy free music in St. Augustine performed by local singers, discovered find this church-sponsored series, held monthly. It's a masterpiece blend of an art walk, usually happening from 5-9pm every first Friday, with beautiful notes of choir, organ and orchestral music.

Milltop Tavern and Listening Room

19 1/2 St. George St., St. Augustine, FL 32084

Enjoy live music just about anytime at Milltop Tavern. With free live music strumming two to three times a day, every day, it’s a good bet you’ll be there for some catchy, sing-along-style tunes.

This converted gristmill from the 1880’s has history and an amazing central location. For a bonus, they’ve got great bites and a lovely rooftop. All are welcome!

Pierre’s Pub

69 St. George St., St. Augustine, FL 32084

New to St. Augustine from 2022, Pierre’s a little-known gem on St. George Street offering up music daily. Enjoy drinks from their beer and wine selection and tap your feet to the courtyard grooves.

Prohibition Kitchen

119 St. George St., St. Augustine, FL 32084

Boasting awesome live music every evening, this centrally-located spot with speakeasy vibes is a fantastic place to kick off your heels and let your hair down. Enjoy creative cocktails from yesteryear and a variety of music to suit every genre taste.

The Pub on Anastasia

213 Anastasia Blvd., St. Augustine, FL 32080

Not quite a live music venue by typical standards, but watch your neighbors and your friends take the stage instead, because every night is karaoke night at The Pub! They also have late night pub grub, beer pong and darts so you’re pretty much covered with the fun factors.

Stogie’s

36 Charlotte St., #3646, St. Augustine, FL 32084

Don’t be fooled, this cigar bar has a serious reputation for a jazzy good time. With live music playing six nights a week, Stogie’s is a sure-fire bet for that smooth, after-dinner dessert wine, or perhaps the cigarillo you’ve been craving after a long day.

Even non-smokers can enjoy this historic property built in 1888, due to its state of the art filtration system (i.e. no smog filled rooms). Indulge in and choose from over 65 types of port wines, and hundreds of additional beer and wine selections.

Tides Oyster Co.

641 A1A Beach Blvd., St. Augustine, FL 32080

Date night doesn’t get better than Tides. With happy hour specials keeping the drink bill totally reasonable, a carefree evening can be spent at Tides by slow-dancing to old country tunes or rocking out to karaoke music.

Every night is a new offering at Tides Oyster Co. but, rest assured, every night is equally a good night at Tides.

Trade Winds Lounge

124 Charlotte St., St. Augustine, FL 32084

Offering regular music in a laidback bar atmosphere, St. Augustine locals and tourists have been loving this free live music in St. Augustine gem for decades. The trinkets and tiki decor offer an upbeat backdrop to exciting tunes and excellent drinks.

Don't skip a beat… just bop over to these awesome places for free live music in St. Augustine!

Globetrotting since 1995, Maria is a daughter, girl-mom and wife to a Spaniard. She is a karaoke wunderkind, natural born storyteller and creative writer. She’s a wine and gin enthusiast and charcuterie builder extraordinaire. Seeking to inspire others to “Travel More”, she shares travel advice, destination spotlights and more at her site AlwaysPackTissues.com.