16 Best Dive Bars near Winter Park

“We had an amazing and awesome first experience at Thirsty Gator! We went for Oysters and they were fresh and delicious! Our server was Shelby. She was great! It's a great place! Definitely going back. Thanks for the great service Shelby! 👍👍 and great food Thirsty Gator!!“

“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....“

“I had been looking around for a good punk bar and Will’s Pub had incredible vibes. The bands at the Underground fest were so nice, the atmosphere was fantastic, and the drinks were great! The bartenders were chill and there was plenty of room to move around and watch the other bands perform in the different areas. This will definitely be my new favorite hangout spot!“

“First time in here was sitting at the bar and the bartender came within 30 seconds of asking me what I would like. Very elegant place even though it’s a hole in the wall it’s very nice if you come down to Florida, you have to visit this place.“

“Casey’s on Central is hands down one of the best spots in downtown Orlando! The vibe is always great, the drinks are strong, and the music keeps the energy going all night. Every single bartender here is top-tier — they’re fast, friendly, and always make you feel welcome. You can tell they genuinely care about giving everyone a good time. Whether you’re starting your night or ending it, Casey’s is always the move!“

“First off, do not go here if you are looking for a nightclub atmosphere. You will not find it.What you will find is a clean, well maintained bar with fantastic food and friendly service. The crowd is mostly blue collar and retired workers that come in to relax and enjoy each other's company. Every time I have gone in, I met great people and struck up great conversations.The bartenders are cordial and fast at their job. Prices are generally less than any other bar I have visited.The food is better than most bars and I've never been disappointed. My go-to is the cheese steak, double meat, crinkle fries, and grilled peppers and onions on the side. I try to make it a point of getting this at least once a month.The music is usually classic rock or country, not too loud. Overall, a great place to eat and relax with friends.“

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

“We wanted to go somewhere we don't normally go, off the beaten path, just to have a day with friends to hang out and relax outside of our normal routine. The Caboose did not disappoint.Everything was amazing. We ordered a few rounds of drinks, shots, and food. Mozzarella sticks, flatbread pizza, nachos etc,. The food came out promptly and was spot-on. Our bartender Mari was attentive and offered great customer service, even when the POS system went down at peak business she worked through it and still managed to take care of everyone. We spent around $135 and she had no problem splitting the tab as requested. Great experience all-around. Highly recommended.

Vegetarian options: They do have vegetarian options on the menu, including the vegan black and blue flatbread pizza, which is mushrooms, onions, tomatoes, mozzarella, and blue cheese.“

“Went here yesterday for football sunday and was taken care of by shayla. She was super nice, and all the girls were working super hard and made my group and I very happy! Thank you shayla, madi, and gwen. You guys are great and will be seeing me next sunday for some more wings and beer B).“

“Was a fun dingy place to play. Perfect for a punk show although a very tight squeeze. I'm not sure what food was offered, but basic variety of beers that you cannot go wrong with.

Vegetarian options: Idk.

Dietary restrictions: Idk

Parking: All up and down the avenue. The parking is spread out pretty well!

Kid-friendliness: Don't think you're going to get kids inside LOL.

Wheelchair accessibility: The entire space is one room so you will definitely be fine wheeling in.“

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

“Always Great place good food and drinks“

“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.“

“Awesome place. Best place in town.“

“Great place in downtown Orlando. I stopped in here before an Orlando Magic game and the atmosphere was perfect. They have nice drink specials and good dj. Plenty of music and drink specials. See Matty for VIP specials. Make sure to tip well. Love this place.“