The atmosphere was nice, band was amazing however, it was extremely over crowded, bar staff was rude, servers are even worse, especially the one smaller white woman with the DREADS?! And if you're not comfortable with being grabbed by your arm by one of "The Girls!" to be moved out of an obviously overcrowded aisle, DONT GO! Also you will get comforted, dismissed and talked down by what I'm only to assume, was the the owner; lates 50s white woman with white tank and an old cowboy hat & her overly buff older dude! The kicker, I was told, " I must not be from the "area" because folks here are ok with being touched and displaced by "The Girls!". So we left and will never return; told my finance that spot was definitely off our bar crawl for the wedding! Just upsetting that folks still act so pretentious and rude to people they don't even know! I felt targeted both racially and because of my sexual orientation. IT A LOCALS ONLY HANG OUT PERIOD! JUST WALK ON OVER TO "NO NAME" and thank me later! read more

There's so much to do in STA and so many different types of bars, restaurant and lounges. This place just isn't my jam, but that doesn't mean others don't have fun here. There was live music the weekend we went, and it was super loud and you couldn't hear your friends at all. The drinks are simple and easy and the prices are super reasonable. If this is the kinda spot you like to hang, you won't be unhappy. read more

Stoked to have discovered this laid back local dive just out of the suffocatingly touristy center of town. Sufficiently dim and gritty but with actual good table service from sassy waitresses and strong drinks. The band on stage featured actual musicians playing fantastic classic rock covers while drunk regulars swayed in the background. Cheers! read more

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In the words of "Toby Keith", "I LOVE This BAR" Always a must stop while visiting St Augustine. Drinks are strong. Bartenders are always friendly. Live Music is a norm! If you have nit visited put it in your list! read more

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Live music dive bar. I truly can't live without it. Popcorn machine, a few regulars (bless you for putting up with all us tourists) and a friendly and fast bar staff. We'll be back for sure. Also, the restroom was spotless. read more

Super fun dive bar. Loved watching the live music here on a Sunday afternoon. It is very loud, so only go here if you are up for watching the band. They have plenty of tables and chairs and a waitress that will come by to bring you drinks. Short and sweet review, but wanted to show this place some love. We had a lot of fun here! read more

Tradewinds Tropical Lounge & Grill - Bars Near Me - Saint Augustine, Florida

Cool little diet bar right in the center of Saint Augustine. Live music most days. Today is Monday and there will be music starting around one. Great service cold air conditioning worth a stop.. read more

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We are from Nashville and love local places. We come here every time we are in town. One of our favorite local places. Service is excellent and music is great! read more

Stopped by this local bar in St. Augustine. They have a quirky tropical themed atmosphere offering regular live music. We found a table to listen to the singer Elizabeth Roth performing on Saturday 1 to 4:30pm. We enjoyed her music while having a beer. read more

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We were walking past the Trade winds and hear the band playing ...we circled back and stopped in for a couple of drinks. Greeted my Mark the bartender and he was very nice and attentive... the band "the usual Suspects " is excellent Highly recommend this pub if you are in the areas read more

We were here on a very busy Christmas Eve late afternoon/early evening. We had stopped in at a handful of other places that had either no room to sit or over an hour wait. Interesting dive bar with an eclectic crowd and decor. Everyone seemed to be having a great time. We were just glad to have a seat and enjoy a beer. Live entertainment started up right before we were leaving and they sounded pretty good. read more

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Nice little dive bar. Band playing was good. Drinks were cheap and very tasty too. Right in the heart of downtown historic St. Augustine, good location. read more

Tradewinds Tropical Lounge & Grill - Rum punch $6 special! - Bars Near Me - Saint Augustine, Florida

Your typical little hole in the wall bar located in St. Augustine. It's a find your own seat and sit and wait until the waitress comes over so if it's busy good luck. The day we went it was fairly busy with live music going on so we didn't mind waiting a little. The waitress was super friendly and got our drink order quickly and opened our tab. A few moment later our drinks were delivered and she told us to flag her down incase we wanted a second round. The beer was cold and the prices were pretty decent for being in the heart of St. Augustine right near the most popular area. The clientele seemed to be mainly locals and everyone was super friendly. I would probably stop by here again next time I'm in the area for sure and wanting a cold drink on a hot day! My only complaint was the bathroom was a little messy but being a hole in the wall place I am not expecting a 5 star cleaned restroom, especially on a busy day. Overall a nice place though to visit! read more

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Loved this place. Can't wait to return. I am from Charleston,SC. Music was awesome. Super friendly people. Left at 1am but didn't want to! Local husband and wife in the band. And I could smoke inside w/o being made to feel like a child molester!! read more

My friend and I stopped by here because it looked interesting. We ordered Long Island ice teas and they were absolutely wonderful. Marielena was a fantastic bartender. Had a wonderful time with her. Met the two afternoon singers. Place was so personable. Bought two tshirts so I could advertise for them. Cannot wait to go back! Vickie O. from Gainesville read more

Mark Hart awesome as always! Holly is an astounding guest consultant providing only the finest beverages!!! read more

Tradewinds Tropical Lounge & Grill - Shots and Beers from Holly! - Bars Near Me - Saint Augustine, Florida

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Fantastic bar keeps! Service was on point! Fun live music! A/C was out but they had fans and it was still cool. Had everything we wanted. Clean bathrooms despite the dive bar vibe. Beautiful view of the water and Bridge of the Lions. Would happily return when in St Augustine. read more

Rude staff, terrible service. You can easily walk to plenty of other bars, so, I'd suggest doing so.

Was in town there visiting family and the staff here are rude and with poor service. Only bright side was the nautical theme.

If you are looking to get your song and dance on, walk in! haha. PBA smoking is allowed inside the bar but there is always live music playing and people dancing on the small allocated dance floor, which makes it super fun! If you sit at a table, a waitress will come by to take your drink order and our waitress was very attentive. They don't have a food menu but the table next to us had several pizza's they ordered from a close by restaurant, which the bar allowed them to bring inside and they shared with us! I thought that was super cool! The crowd seems to be an older generation but a fun one! Everyone was there to have a great time, which made the singing and dancing even more enjoyable! read more

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Service was horrible, but way better than the food. Any place within walking distance would be a much better choice.

My favorite stop in Saint Augustine had to be Tradewinds. This joint is an authentic dive bar, with great clientele and cool breeze drinks. Our group tossed down shots of Jack and Peanut butter and Jelly Shots most of the night. And we never had to wait for a round. Besides some awesome service, this bar had a Kickass band that kept things moving all night long. Everyone was all smiles at Tradewinds, making it one of my favorite finds in Saint Augustine. read more

Mark the bartender was awesome the music was fun. Best line ever "this is the drinking part of the song " a must go if you're in the area

Located in the scenic St. Augustine is historic downtown. Great bartenders and servers. Fun crowd. Great Band! Had my favorite Bulleit bourbon. Went for a capper after dinner but stayed late. OUR new go to spot for live music and a good time. read more

We were having a great time late afternoon with bartender Mark then they had a shift change and Holly was our bartender. She definitely should find a different line of work. She's so unfriendly, can't smile at anyone unless she knows them. She's slamming things, cursing, totally ruined our time there. She's definitely costing the other bartenders money. When we closed out with Mark we left him $15 on a $30 tab. Because of Hollys attitude and lack of customer service skills, we only tipped her 10% and that was a stretch. We felt bad for the people working behind the bar with her. We decided to go down the street and spend our money at a place where people actually enjoy their job. If our rating was solely on Mark it would have been five stars. Should barely be one star based on our experience with Holly. read more

Went here for a fundraiser. The staff is very attentive, checking in often to see if we needed to refresh our drinks. They even participated in bidding during the auction which benefited a local boys' group home. It's been the venue for this particular auction for decades. Gotta love when an establishment and its employees give back within the community. The extra star is for the staff. Yes, it's definitely a dark, dive-type bar and, as indicated by all other reviewers, quite smokey. I'm pretty sensitive to smoke but I was there for over 6 hours for the event and was breathing just fine - I brought my inhaler just in case but didn't need to use it! PARKING - there's a paid lot next door ($12) as well as multiple metered spots immediately outside along Charlotte Street. All metered spots on the street are supposedly free after 5 p.m. but read the meter signs to be sure. This bar is located around the corner from Plaza de la Constitución so if you don't mind smoke and an older, laid back crowd, stop in here for a drink and live music after catching the Nights of Lights on the plaza. The Jolly Watermelon was my drink of choice. read more

Tradewinds Tropical Lounge & Grill - Bars Near Me - Saint Augustine, Florida

Good times, good music, good beer! The lady bartending was very funny and very attentive to customers.

I was afraid to come here but stopped as part of a BeetleJuice cocktail tour. So glad we came here! We were here early, around 7pm on a Friday night and they had live music, plenty of seats and a popcorn buffet! I recommend it for a stop for drinks with friends. read more

We have been here 3 different times, with the same experience each time. The bartenders at this bar are the worst bartenders i have ever had in my entire life. They are incredibly rude as soon as you enter. They act like it is there job to be rude to you. Do NOT come here. read more

Tradewinds Tropical Lounge & Grill - Bars Near Me - Saint Augustine, Florida

Great place for drinks and music. There entertainment calendar can't be beat anywhere. Service was good. If you are looking for something to eat, they have great popcorn. No other food-- so plan accordingly! read more

If you would love to have a good time and don't mind a little cigarette smoke this is a nice place to stop in and have a few drinks. My friend and I went on a Saturday night and there was live music which helped set the mood for ladies night out. The place was crowded but the bartenders were keeping the drunks flowing at a super fast pace. They were also serving drinks with a smile. We met several folks while we were there. The vibe was chill and the crowd was nice. The bar dacor had me gazing the room for at least 15 minutes and snapping tons of pics. I'm sure I still missed a few things but I loved what I saw! read more

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You're bartender is a scammer. She charged $18 for three shots of fireball, then $21, then $24. She's f'd her self bc no tip, oh well.

Trade Winds is a really pleasant bar with friendly service and serving a very good drink for a touristy bar. The bar itself is made of beautiful wood and the surrounding maritime atmosphere of the place lends a comfortable relaxed ambiance. It features entertainment at night, but never seems to become overcrowded with the exception of holiday weekends. For the most part, it is more of a local than a tourist place, and if one is to believe what they say, it is the oldest bar in America's oldest city. As for me, I enjoy for a simple quite afternoon drink and some good conversation with friends. It's really in the heart of the area and lends itself well as a meeting place. Though somewhat dive-y it has a wonderful charm about it. read more

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Went down there, couldn't find any parking so I had to leave and go back to the hotel. Pretty disappointing, next time I will either take Uber or walk . Don't drive and think you can park, lesson learned read more

Omg, we randomly found this bar while walking and I'm glad we did. It is your typical, dive bar with cheap drinks and shots but it was so much fun! They had a live band playing classic rock music, they were great. The bartenders and servers were awesome!! We were never waiting for our next drink, she was always checking on us even though she was busy. I wish I could recall her name because she was hands down the best!! They are open late and the vibe is just laid back and cool. Come dressed up, in pajamas, no one cares! I would come here again next time we are in town for sure. read more

Rudest female server ever. She yelled at us for asking for a drink. It was super busy ... I get it. We asked for a drink ... she said "sure, in minute..." and then passed us by. We lightly touched her because we thought she accidentally missed us on the way back and she screamed at us in an extremely aggressive and abusive manner. Yes ... perhaps we should not have touched her but we honestly thought we were helping remind her. I am a bartender in a very busy bar and would NEVER treat any customer the way we were treated. We were not drunk, pushy, or threatening. We were calmly sitting and nicely dressed. Perhaps the bar should have more servers if the ones who are serving can't handle the workload. read more

If you want to lose your hearing to a lousy band, go there. The name of the band is Jackhammer, and honestly, I'd rather listen to a real jackhammer. At least the construction worker might be hot. read more

I love Tradewinds! We hit this bar every time we visit St. Augustine. It's a fun dive bar. There is smoking inside so if that bothers you then you would probably want to steer clear. The service is good here. Prices are reasonable and bands play on the weekends. Overall the atmosphere is super chill and people here are all having a great time. I will definitely continue to come here! read more

Ok, so it seems to be an all American bar. Drinks and music is just very American. Margaritas are good, or top of the line, beers are good and local. Musician was seemed to be a local boy which is always nice to see. Appreciate a good bar, good drinks, and good music. read more

Always a great time meeting locals + tourists. Lots of boat people. Always great music + strong drinks. Admittedly I liked it better when you could smoke inside. Smoking kept it adults only and yuppie free. read more