Enjoy the best restaurants, bars, and night life in the historic district of St. Augustine, Florida!
Did you know that St. Augustine, Florida is often referred to as the “Nation’s Oldest City”? It has a rich history dating back to the 1500’s when Ponce De Leon landed here, and is truly a magical place to visit.
But what’s so great about St. Augustine is that it embodies such a mixture of being a lively city with plenty of great restaurants, bars, and live music venues, while maintaining the history and culture. If you’re planning a trip to St. Augustine soon, we’ve got you covered with a list of the absolute best restaurants to try. Trust us, you won’t want to miss out on these tasty spots.
Best St. Augustine Restaurants in the Historic District
St. Augustine is known for “Florida food”: think conch fritters and seafood, Southern-style food like fried green tomatoes and shrimp & grits, and of course, key lime pie. And yes, all of these are oh so good! But that’s not all the city has to offer. If your mouth is watering now, keep reading!
The Floridian
Nestled among the many winding streets of Spanish Street, The Floridian is a charming restaurant favorited by locals. Come for brunch and try the fried green tomatoes and shrimp and grits- two classic southern dishes.
The ambiance of the restaurant is an intimate and cozy experience, with its covered courtyard that is surrounded by lush tropical plants and trees. This is a great place to start your day in St. Augustine– don’t worry, you’ll walk it all off later!
The Floridian is tucked away on Cordova Avenue and it is easy to miss the sign. From the Trolley Tour the Floridian is a short walk from several stops, including the Old Drug Store or from St. George Street.
Columbia
Ah, the Columbia. One of our top 5 favorite restaurants of all time! The flagship restaurant is in Tampa, but there are also locations in Sarasota, Clearwater, and St. Augustine.
Claimed to be “Florida’s oldest restaurant”, the Columbia has been owned by 5 generations now so the food tastes the same every time you go (which is definitely a good thing)! If it’s your first time, get the 1905 salad and the ropa vieja, you will thank us later.
Prohibition Kitchen
If you want great live music, tasty drinks, and a juicy burger, Prohibition Kitchen is the place to go. Right in the heart of downtown off St. George Street, this gastropub has a live band performing on the indoor stage nearly every day of the week. It’s a great spot to pop into while walking through downtown to rest your legs for a bit- unless of course you feel like getting up to dance!
Harry's Seafood Bar and Grille
Honestly, it’s hard to get a picture of Harry’s Seafood Bar and Grille without people lined up to get in. In fact, Harry’s is probably the busiest restaurant in the St. Augustine historic district. It’s that good, and it is well worth the wait.
Tip: They don’t take reservations but there is plenty of seating in the covered courtyard, as well as tables inside and upstairs. There’s a separate bar upstairs that is first come first serve seating, so try to grab a few seats at the bar to avoid the wait!
Since the restaurant is directly across Avenida Menendez, you can watch the boats in the marina if you have a seat by the windows upstairs. At Harry’s you can order seafood and New Orleans style meals, and the chowders are phenomenal!
Milltop Tavern
The Milltop Tavern has bar style food, really good drinks, and live music every day. Grab a spot on the upper deck to have the best views overlooking the Castillo de San Marcos! It’s in the perfect location for people-watching (my favorite past-time), and for sitting in the shade to get out of the Florida sun for a bit.
Best Waterfront Restaurants in St. Augustine
You can’t come to St. Augustine and not see the beautiful sunsets! Even better if you are enjoying a cold drink and eating yummy food while the sun sets. The best restaurants on the water are on Anastasia Island, directly across from St. Augustine via the Bridge of Lions. Read all about our favorites!
Best Bars, Wineries, and Night Life in St. Augustine's Historic District
St. Augustine gets a completely different vibe once the sun starts to set. With all kinds of live music coming from every turn, there are so many fun things to see and do here in the late afternoon and evenings. Read along for our favorites!
San Sebastian Winery
San Sebastian is the sister winery to Lakeridge Winery and Vineyards in Clermont, FL. Both wineries utilize muscadine grapes grown in Florida, so they mainly produce sweet wines best served cold which pairs perfectly with a hot Florida summer!
If you’ve never been before you should do the (free) self-guided wine tour with tastings. If you have already done the tour and want to head right to the action, go to The Cellar Upstairs for live jazz and R&B music on the rooftop every Thursday through Sunday. They serve local beer, wine, cocktails, large appetizers, and sandwiches. The blue cheese chips with balsamic glaze are worth the trip alone!
Bonus: The Trolley Tour picks up and drops off right out front so you don’t have to drive if you bought tickets!
St. Augustine Distillery
We’ve been to the St. Augustine Distillery twice, and the tour has changed a bit due to Covid. Now the tours are self-guided with tasting stations spread out, and the tastings are actually mini cocktails made with the distillery’s own tonics and mixers. Much easier to try than a shot of straight vodka in my opinion! Their gin and house-made tonic was very refreshing.
Tip: This is another stop on the trolley tour, along with the Ice Plant (see below).
Ice Plant
If you are into craft cocktails with fresh and unique ingredients, you must try the Ice Plant. They have a full farm-to-table menu and specialty drinks. Fresh house-pressed juices, unique bitters, specially developed syrups, and three different kinds of ice go into creating these tasty concoctions.
Located in a large industrial factory building dating back to 1927, the Ice Plant has two wrap around bars and an upstairs outdoor bar seating area, so you can always get a great seat. We tried the Lady Killer and Dirty Rotten Scoundrels cocktails… we couldn’t pick a favorite!
Sangria's Wine Bar
We just can’t get enough of Sangria’s Wine Bar! It’s such a warm and welcoming spot to unwind after dinner on the second-story deck. Plus it is in a prime location just off St. George Street, with live music and a delicious pitchers of sangria. If you’re looking for fantastic tapas and some of the best homemade sangria – red or white – around, this is the spot for you.
The Tini Martini Bar
Situated right on the main Avenida Menendez is the Tini Martini Bar at the Casablanca Inn. For over-the-top, knock you on your behind martinis, this is the spot!
Enjoy a bikini martini, espresso-tini, or lemontini as you sit outside overlooking Matanzas Bay. Or have a glass of wine, beer, or premium liquor inside the cozy bar area. It’s a great place to relax after eating, shopping, and sightseeing all day. Just a word of caution: These drinks are strong!
Ancient City Brewing
Directly across from the town square and Plaza de la Constitucion is the Ancient City Brewing Taphouse. It’s a cozy place to grab one of their craft brews, plus they have happy hour M-F, weekly specials, and live music on the weekends. None of the beers are gluten-reduced but they did offer several gluten free cans of ciders and seltzers. David really enjoyed the Matanzas River Red Ale!
Whether you’re a foodie or just love trying new places, it’s always exciting to venture out and discover local favorites and hidden gems. And don’t forget, there’s always room for more adventure! If you enjoyed this guide, be sure to explore our other “best of” series for more inspiring ideas. Keep exploring and never stop discovering new tastes and experiences!
Happy travels!
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