As the name implies, this jazz bar specializes in one indulgence above all others: cigars. The cigars are as close to Cuban delights as one can find in the US (though the offerings are mostly Honduran or Dominican), so those looking for Cohibas might be disappointed. The atmosphere is relaxed and mellow, but can be lively depending on the weather, time and the act on stage. Again, as the name implies, jazz is the main musical course here, but sometimes different sounds or the occasional DJ make their appearance.
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.
The Cellar Upstars Wine Bar is located in St. Augustine's very own San Sebastian Winery. Of course, most of the wines come from the estate, and though Florida is not synonymous with Napa Valley, remember that it was this part of the coast where French Huguenots first cultivated the grape in the Americas. The Cellar is only open on weekends, but the winery conducts tours throughout the week. If you do make it while its open, the Cellar has a great patio deck where you can sip your vino and listen to live music.