6/10/2022 A last minute change of plans landed me in Winter Garden. We closed the night at Pilars. Other than a delay on one drink, everything was good. One friend raved about the margaritas. I had a beer so can't speak to the cocktails. On my Middle Class Monotony (MCM) scale (0-5 where 0 is NOT cheap or monotonous and 5 being very cheap and monotonous): The prices aren't too expensive and it isn't difficult to get in so I'm going with a MCM of 4. This isn't a bad thing it just means i could easily do this on a regular basis. 3/19/2022 We had some time while waiting for our table at Winter Garden Pizza Company and Downtown Winter Garden it's so walkable, that we stopped for a drink at Pilar's. My receipt says our server was Gina but I'm pretty sure that wasn't his name, but he took good care of us. My wife's Sweet Tart was very tasty and i enjoyed the Irish Red. Happy Hour? I'm down.

Absolutely amazing! Great assortment of wines and spirits. This place is absolutely the definite place to come in on Thursday nights. With live open Mike singing , you're destined to experience it all. Parking is a concern, you're better off Ubbering. Noise 7/10 ambience 6/10 parking 3/10 service 6/10

Has turned a nice clean historical building into a trashhole. Alcohol glasses, beer cans and bottles, vomit and urine are now the words I would use to describe the Roper Building. Don't believe me? Try using the elevator, smells like you're in a giant urinal.

Just leaving Pilar’s we got there 12:20am and did not get served any drinks. They closed at 1:00am and we still did not get served or were even acknowledged… purposely ignored us and other guests. I’m speechless because I saw the two bartenders at 1:00am serve themselves drinks from the bar while multiples guest and ourselves were still waiting. They literally had shots from the bar infront of us guest with no care. Hence, we have all been waiting more than 30 mins and no acknowledgement/service. I will definitely not recommend this bar. Instead the one across called the whole enchilada had better service and were respectful. I don’t know how this place has even 4.0 reviews it’s mind blowing … I will contact manager directly

Love this local bar so much. Every time I come here Gina always takes such good care of me. Gina is personable, knowledgeable of the menu and liquors and is true mixologist. I always recommend Pilar’s martini and Gina in specific. Love coming here.

Fun time at a Scotch Whisky tasting. Definitely going back!

This was by far the worst experience of trying to book this venue I’ve ever had. The experience manager was very unprofessional, not responsive for emails, I had A set date, due to the lack of communication, I was Set back in finances, if you plan to book this event, it seems as if this location filters who they want to take on as a client. I do not recommend this location to anyone in the near future!

Was absolutely disappointed thought service was unbelievably rude. Waitress totally ignored us when we first walked in then came to take her order and actually gave my fiancé an attitude and made her feel very embarrassed as she began to make racist comment.I honestly thought Winter Garden has come along way but was definitely wrong would not recommend this place to anybody seeking any kind of diversity Or any kind of complementary service or just plain looking for a good time on the Fourth of July going to be calling around tomorrow and see if this is a chain of restaurants and going to make a corporate complaint.

Like to sit out side. Drinks are fairly strong but not overwhelming. Bartenders are nice but it can be packed! Great martini menu. A little pricy. They do music nights. You can order food also here but they get it from a near by restaurant. been here 4 times and will go back

Tracy, our bartender was quite pleasant as this was our first visit. She gave us the run of the land and boy could she mix a drink! After my wine, I had to taste the drinks a Woodson and Grand Margarita that were outstanding!

Late night drinks with friends. First time, but I'll be back! Terrific atmosphere. A hip hangout at night and felt like a modern day "Cheers". The crowd was friendly and full of energy. Plus, our drink orders were spot on!

This is my favorite night spot of all times. The atmosphere, service and quality of live music makes this place the most outstanding gem in central Florida. I recently saw Matt Catingub and the new Plant Street Pops Orchestra, incredible talent from around the country. A truly magical evening. We are so lucky to have this in our community. I will go back often. Michelle Amato is one of many very talented performers that I will see again and again. Martini / drink prices are actually very reasonable and a great and creative selection are available. HIGHLY RECOMMEND!!!

I am a big fan of the atmosphere at the Pilars second floor loft. It really is a totally different vibe from the downstairs bar and the cocktails are very good. I especially enjoy the live music they frequently have there.

Good, Service & Atmosphere is all on the Superb side of things. This is truly considered Orlando’s hidden gem, everyone is always welcomed with a smile and great attitude by the staff. Let’s talk about the diverse drink menu, every time I consider trying something new . ( my to always have drinks here are the Godiva chocolate martini & the Pilars Have S’more ) but all others I’ve tasted have been great also. The appetizers, a must have if you’re staying for their live music event, again a true hidden gem for Orl. the vibe here is always soul grounding .

Great local bar to grab drinks. I did not order any food, only drinks. The atmosphere is quite loud and they could benefit from some acoustic dampening. Drinks were pretty standard and I didn’t order any specials they had. I’d come check this place out again.

Absolutely love this place! The bartenders are always super awesome and friendly and the drinks are the best around! We love the uncle Kate the most 💙

This place is just my vibe! Simple yet fun. Their drinks are amazing and their service is awesome as well! Great atmosphere 👌🏼 I will definitely be back again soon.

Gina was a fantastic server. Great atmosphere. Outdoor seating available. Apparently there is sometimes an upstairs piano bar but we haven't experienced that yet. My wife loved her s'mores martini. Lots of regulars. Easy access if you park at Plant Street or the garage. Food available from next door.

Had the honor of attending a Jazz concert upstairs, one of the best music experiences of my life, the musicians were all beyond amazing, and the atmosphere is perfect for enjoying music without feeling overwhelmed or overcrowded. As someone with very bad social anxiety, I was able to relax and enjoy the show without feeling like anyone was looking at me, and we were sitting in the very front row. The music and atmosphere was so great, everyone else was just as caught up in the performance as I was. A great night out!

We love going to pilars! You can get a large selection of drinks on the craft menu. Everything I go, the drinks are good and generous. We love watching the musicians. Sundays they have an option to bring your own instrument and jam with others. Really cool seeing the people bring their talent and fit right in. Parking is free street parking or free garage nearby. Weekends are busy but bartenders always ready to help. They carry dobel, my fave tequila.

We didn't know that Pilars even existed. What a great venue. Michael Andrew's was phenomenal as always. We had a great time. We'll be back.

Best spot in downtown Winter Garden to have cocktails. Nice atmosphere, great drinks, and hands down, the best bartender around in Brian.

Great live music. While not a big jazz person, the music was good and we enjoyed the atmosphere. The drinks were very good and not expensive.

Pilars is my go to bar, I love my bartenders there.. Gina and Brian have known me for years, and always know what I want when I come in.. It is a great spot for locals to get together for any occasion on any day of the week.. Jazz nights are amazing, the drinks are amazing, the environment is safe and lively.. Bartenders are always attentive and kind... wide varieties of mix drinks from normal mojitos or coke mixes, to more sophisticated martinis, infused cocktails and more!! Come experience the best bar here in Central Florida if not all of Florida.. Thank you Pilars!!! 💜💜

The atmosphere was fantastic! The downstairs is perfect if you want to have conversations with strangers. The drinks were great! We got both of the strawberry drinks and they were delicious!

Tracey was awesome. Kept up great conversation and great drinks. Will always come back to pillars for the consistent service. Thank you for a great Saturday.

Private party beautifully presented food, very polite, friendly and gracious staff. The room is gorgeous with lighting that makes everyone look terrific. Highly recommend it.

Pilars Martini Bar is a great local spot in downtown Winter Garden. We stopped by on a Saturday evening after having dinner nearby. We sat at the bar and the bartenders greeted us quickly. We were looking at the menu online and they gave us a printed menu after we told them it was our first time in. It was much easier to read all the drink options on the laminated menus. I typically enjoy a dirty vodka martini and don’t really like fruity drinks but wanted to try something different. Tracey suggested the Cucumber Cosmo and I’m glad she did. It was tasty, crisp, and easy to sip on. My husband had the West Orange Crush. It was fresh and balanced & he enjoyed it. The bartenders were very friendly and told us about the events they have throughout the week. They told us there was live music upstairs in the loft so we decided to head up there. The loft is a really chill spot with a diverse crowd and the music was great. It was an awesome date night. The service upstairs was great too. We enjoyed our night out and are looking forward to stopping by for an open mic night in the future.