17 Best Dive Bars near Winter Park

“Big fresh oysters! Raw ones were awesome and fully detached from the shell, easy to tell they were fresh...Oysters Rockefeller were really tasty too and I am not the biggest fan of them usually...Beer was super cold and the service was fast and friendly...Was pleased with the price because the tab was less than I expected..Great Local Bar atmosphere and being a Gator fan, I really liked the decor here...Will definitely be back...“

“Great food, great atmosphere“

“good service and good vibes“

“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!“

“It's a long story........“

“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).“

“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.“

“Anyone give this place less than a five star probably an a* h*. Which is fine not all people are great anyway. Cheers of Orlando, Excellent Atmosphere, great musicians all true American style, Business culture shows that the ownership is not looking at you as a mere transaction but a cherished companion. This is evident thru the dedication and longevity of their staff some of whom working here like 20 years and they are still passionate of what they do. Whether you are all by yourself or on a date or celebrating birthday this is the place will make your day memorable. Truly affordable menu in town also makes me feel like the owners treating this like a community service more than a business. Real girls working here whom have a true beautiful smile that resembles the warmth and kindness that resides within their heart instead of a mere facade to attract more people to come. Even at the first time you step inside, familiarity and safe feeling washes over you like you have always been there. Great job guys, we, trully appreciate that you choose us as a customer. Thank you.“

“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.“

“I love the vibe of tanqueray. It's the only issue I have with it is that it's smokey down there. Which borderlines stuffy. If have allergies do not go here. Other than that they usually have a live band with music playing and the service is good.“

“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.“

“If super dive bars are your thing, this place should be on your list. Went on a Tuesday, so not sure what the weekend vibe is like, but it was really chill on a Tuesday. The drinks were great and the service was attentive. I definitely want to go again. It's nice to have a place that serves liquor other than Milkhouse in the neighborhood.“

“Awesome place. Best place in town.“

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

“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.“

“Always Great place good food and drinks“

“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.“