Sir Winston Wine Loft & Restaurant

I came in late in the evening and ate alone at the bar. Sarah the bartender was so nice and welcoming, and made great recommendations. I ordered three small plate items and a signature smoked cocktail. The food was great, and the drink was not only delicious but a presentation. spectacle. I topped it off with her dessert recommendation. All in all a great experience. Go visit Sarah.... She a top notch bartender and delightful conversationalist.

Our waitress was great and the food was delicious. I had the branzino dish which was served as a whole and husband had the steak frittes. Even our drinks were yummy.

At 530 on a Saturday (pre show) we arrived as the first diners. Shame on us for not knowing how the pre show thing works in WS. Turns out we were just 45 mins early as the bar, replete w football on tv, filled up. The wonderful bartender came right over and took our drink order, followed by our equally wonderful waitress who took it from there. The beef Wellington was memorable. Keep in mind if ordering it logically takes a while to cook to temp. A very nice experience. Thank you.

Busy night last night but they couldn't keep up. Kitchen was too slow and took insane amount of time to get our food. Wait staff was nice and apologetic but couldn't do anything about it. Food was average.  cocktails were very good.

Our server went above and beyond to make sure we had everything we needed. Even though the restaurant was busy, we never felt rushed. The little details - from the perfectly chilled glassware to the timing of each course - made the night memorable.

The design of the restaurant, the value for what you get, and the ease of getting in and out of there considering it's location are all factors that warrant a return visit. I was surprised that we were the only customers there, aside from one other table. We had three in our party and my son loved his lasagna. The other two meals weren't great -- just very bland and not a lot of flavor. Despite that it's a great location downtown and definitely worth another visit. Use the valet as it's only $5 if you are just stopping for a meal here. A great value and highly recommended!

The restaurant was nice, but the service was questionable. My wife and I waited over 20 minutes before someone took our orders. When our food arrived my wife's order was incorrect. They took the order back to the kitchen and removed the item and just replaced it with something else. When my wife received her food it was cold. The manager did removed the cost of the item from the bill. I don't know if I will return due to my experience.

Absolutely lovely- was here for the wine dinner. Excellent pairings. The quail was superb. The service excellent. A true downtown gem.

It was a wonderful evening. We enjoyed multiple platings showcasing Georgian (as in former Russian communist empire Georgia) wines. We celebrated their oldest wine traditions and at least 8000 years making wine. The kitchen prepared excellent dishes which paired very well with a very wide selection of wines. Service was great. We will return!

The food was great. The server we had was HORRIBLE! She actually blamed a person at the table for her mistake! She was AWFUL!

The Sunday brunch was amazing! Food was hot and very tasty. The live jazz made our experience extra enjoyable!

The weekend jazz brunch was like winning a treasure hunt. Talented musicians in a great setting. Attentive staff and nobody rushing us out to turn the table. Can't wait for the next jazz session...where brunch might break out!

The staff at Sir Winston really looked out for me in every way. Being allowed a private dining experience in their Loft for a last minute date night was amazing. We had Champagne and Calamari at a table overlooking the foyer and bar, then entrees by candle light. The food and service was outstanding. Christine, our waitress, was super attentive catering to our every need. The combination of ambiance, privacy and service made for a perfect occasion! Highly recommend!!

Such a hidden gem. This place was amazing. The fruit plates they offer with the water was such a nice touch. I had the signature old fashioned to start, and it was so delicious. My server Christine was very knowledgeable and helped me choose a cocktail. The fritto misto was great, very crispy, and the sauce that comes with it was such a nice touch. I also had the steak frites, which was cooked to perfect temperature. For dessert I had the Guinness chocolate cake, and again, all 10s across the board. This place needs to be packed 24/7. Best food I've had in a long time, honestly. I went to sit upstairs to finish my cocktail and the view from up there is great. I stopped on my way out to grab a glass of water and even the guest waters they have out are spectacular. Full of fruits and so nicely put together. 10/10 would recommend

I visited sir Winston on 08/15/2025. I was hesitant on visiting this restaurant due to prior reviews & comments on the service. However, I saw panna cotta on the menu & have not had any since I visited Denmark in May(it’s hard to find in NC). I decided that the octopus and panna cotta would be worth the possible poor service (I can always complain to a manager).

Needless to say, I’m glad I acted against my better judgment. It is clear to me that the management is committed to redeem themselves and improve their service. I was greeted by valet, the hostess, and the server. Moreover, our server was very friendly, knowledgeable about the menu, and extremely attentive(give her a raise and have her train future servers) . Our waters remained full and she always checked on us to see how we were doing.

A luxe touch that I really liked is the fruit tray the server brings around that includes lemon slices, strawberries, blood oranges, and blueberries to add to our water! This is a level of service that I did not expect to come across in Winston-Salem or really NC at all. Another nice touch I like is that the menu has a country flag next to each dish. For example the beef Wellington has a UK flag & the charred octopus has a Greek flag. I can appreciate such things.

Moving on to the most important part. The FOOD!! We ordered the calamari & octopus as appetizers. The octopus, although charred, was cooked perfectly. I believe that this dish could be elevated with a chimichurri sauce instead of the garbanzo bean salad. For an entree we did lasagna & the beef Wellington. My Wellington was a little raw. In order to avoid this I recommend ensuring that it fully rests and do not cut it down the middle. I understand the pressure of bringing out both entrees. However, this pressure can be curb by advising the server to properly advise guests that the Wellington can take 40-50 minutes. (All things considering -Everything was delicious)

The sous chef/manager cooked my Wellington a little longer to get it to the perfect medium. He was very friendly & understanding. I really didn’t make a big deal out of it, because I understand that these things can happen. I care more about rectifying the situation and proper service. The staff at sir Winston exceeded all expectations.

My panna cotta was amazing. It was served with peaches and strawberries, which is different and delicious(I’m used to just mixed berries). I ordered an espresso martini with house tequila instead of vodka. Arguably the best espresso martini I had- this side of the Mississippi.

Just based off the taste of the food & the service I received tonight- Sir Winston is easily one of Winston Salem’s best restaurants. I’m actually surprised that it’s not packed. I hope that more people give it a chance. I’ll be back with my fur baby !

Atmosphere: 5

Food: 5

Service: 5