16 Best Dive Bars near Winter Park

“Thirsty Gator is where strangers go to feel like long time friends. You can tell they have a set of regular customers, however, you always feel welcome when patronizing. The service is always top-notch. My fiance and I love sitting at the bar and chatting with folks. The rock shrimp is my go-to, but the oysters are next on our list. You can tell they put Karen to everything they do, including the food. We look forward to the next time!“

“Great food, great atmosphere“

“I love this bar but Saturday night I paid my tab for 109.00 woke up Sunday and the charge was 170.00 on my card waiting for them to open because I need answers and my money back....“

“The atmosphere is relaxed, making it a perfect spot to unwind after a long day. The staff is friendly, attentive, and always provides excellent service. The drinks are well-made, the prices are fair, and the overall vibe is fun and enjoyable. Whether you’re stopping by for a quick drink or spending the evening with friends, this place is definitely worth a visit. Highly recommended! 🍻🎶“

“LiL iNdieS n Will’s ROC ¡“

“Walked into the Caboose Bar for a drink and found a great bar to frequent! Our bartender, Alexa, made good drinks and was very entertaining while aesthetically pleasing! The bar has pool tables, darts and good music also has a table or two outside front to sit and watch people go by since it's in a great location ! Recommend going to check it out if looking for a good time, would even feel comfortable going in solo as the people were very nice and inclusive of newbies! They also have some food items but we had already eaten. Love bars like this and bartenders like Alexa so wanted to recommend giving it a visit!“

“The Bar Is Vibes All day. It’s just the Dj they have every other Friday He needs a New playlist Lowkey ssa. lol He’s my guy but if I tell him his music playlist sucks and it’s the same list week after weak. Maestro his name. Cool short dude. Always A good time and the Patrons are Amazing Crowd.“

“I grew up here.. just moved back from Jersey after 27 years.. so, I look like I'm from Jersey.. my bf and I wanted to check this place out. It was super layed back.. cool people and a chill environment. The bartenders were awesome!! I did have a problem with one of their reg“

“Uncle Lou’s Entertainment Hall is exactly the kind of independent venue that gives a local music scene its personality. It has an intimate, DIY feel where original bands, touring artists, and passionate music fans all end up in the same room. Places like this remind you that great live music doesn’t need massive production—it just needs a stage, a welcoming crowd, and people who genuinely care about the experience.

Orlando’s music community is stronger because venues like Uncle Lou’s continue to give artists a place to be heard and audiences a place to discover something new. Long live the independent rooms that keep live music authentic. 🍄“

“awesome people,friendly atmosphere, and as cheers would say, A place where everyone knows your name..lol“

“I absolutely love this place. Everytime I stop in there everyone is so nice and makes me feel right at home and like I'm top priority. The vibe is amazing and time flies because you get so caught up with all the interesting people and staff there. I wanna say an extra special thanks to the wonderful young lady behind the bar there, Stephanie. She went above and beyond to make sure I was well taking care of and never let my glass go empty. If you're looking for a laid back spot to have fun this is your place.“

“Always Great place good food and drinks“

“Awesome place. Best place in town.“

“Good place to hang. Drink. Play pinball. Play pool. Socialize.“

“My first visit and I found a very welcoming crowd. Everyone was polite and respectful of others. Drinks were strong af just like I like. Pet friendly and many TVs for your sports watching pleasure. The food is supplied by 3rd party businesses ,no food prepared by bar.“

“Stopped by for a few drinks and had a great time. Jeff was our bartender and provided excellent service, friendly, attentive, and made us feel welcome. He even put on music we enjoyed, which made the experience even better. The atmosphere was fun, relaxed, and welcoming. We'll definitely be back! 🍻“