The Tradewinds Lounge bills itself as the oldest club in the oldest city in America. Whether true or not, the bar is still located in a charming 18th-century building. Upon entering, the music and Tiki decor definitely give the bar that 'Parrothead,' island-type of vibe (Mr. Parrothead himself, Jimmy Buffet played here at the beginning of his career). There is no kitchen, just pub snacks like chips, pretzels and popcorn, but most people come for the music, camaraderie and cold beer.
Located in the historic Casablanca Inn, Tini Martini Bar is an intimate space that recalls scenes of Rick's Place in that movie named just like the hotel. The martini's are excellent and since they leave you with the shaker, it's basically a two-for-one night every night. The bar provides live jazz, blues and some of St. Augustine's finest local musicians to entertain audiences with creative renditions of classic covers. Even if you aren't a guest at the inn, you still can visit to enjoy the alfresco arrangement which lets you soak in views of the Matanzas River while you listen to sounds under the palm trees.
Shaughnessy's Sports Grill is a sports bar and grill situated in the city of St. Augustine. This place is a good spot if you are looking for classic grilled food to go with cold beers. Come here to enjoy the live music along with a glass of wine, cocktail or draft beer from their bar.
This hole-in-the-wall joint located along historic St. George Street is the go to spot for beer lovers. The bottles behind the bar are primarily of the European variety, however there are several delicious domestic and innovative suds from around the world. The interior is relaxed, with comfy booths and a few tables scattered under the wooden beams. The large refrigerators allow guests to examine their choice of beer better and they are a nice DIY touch to the dining room. Food choices include cheese and sandwiches alongside 'pub-style charcuterie'.
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Chili's
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In the heart of historic downtown Saint Augustine. Quaint, lively wine & tapas bar with specialty sangrias, patio seating & frequent live music.
Barley Republic's is an Irish gastropub that features a large alfresco patio always filled with happy patrons. The fantastic beer list features 60 carefully picked brews from all over the world and if you can’t decide on just one, try the beer cocktail, which is a pairing of beers with complimentary flavors. This public house also has a full menu filled with traditional Irish dishes, a couple of the favorites include the shepherd’s pie, made with whole chunks of roasted lamb or the Guinness-braised beef ribs.
