Sir Winston Wine Loft & Restaurant — Restaurant in Winston-Salem

Upon arriving at the restaurant, I asked if I could take a seat at any table and was advised yes.

The male server brought me a menu and asked if I'd like a drink, to which I requested a black coffee.

The server returned a few minutes later and I asked how the 'complimentary' breakfast worked with the menu. He asked if I had a voucher, to which I confirmed I did not. He said I needed to get a voucher from the hotel(Indigo) front desk.

I approached the front desk and the gentleman confirmed I should have been provided vouchers when I checked in. He then provided two vouchers and confirmed they were for $20 discount from 'whatever' I ordered. OK, not 'complimentary', but acceptable.

I then returned to my table, presented the voucher to the server and placed my order for; the breakfast sandwich without potato, and a side of ham.

The server said the voucher doesn't cover substitutions. I explained that I wasn't substituting anything, I was ordering the sandwich without the potato, and a side of ham. He then left the table only to return a few minutes later stating exactly the same, "the voucher doesn't cover substitutions". I again explained I wasn't requesting anything to be substituted, I just ordered the sandwich, the side of ham, the black coffee, and expected to pay whatever the total was, minus the $20 voucher. He said 'it doesn't work that way .... and that "if I don't understand I should return to the front desk for an explanation" :O

I went to the front desk, alone, and the gentleman confirmed the voucher worked exactly as I described. At which point the server arrived and interjected himself in the conversation, saying, and I quote, "can you be quiet and listen", while again he tried to explain the situation with SUBSTITUTIONS.

AGAIN, I explained I'm not substituting anything. As a result of him interjecting into my conversation, and in effect telling me to 'shut up', I suggested he should remove himself from the situation, return to his job in the restaurant, and I will resolve the issue with the hotel front desk. To which the server responded, "OR WHAT?!"

The front desk representative was completely understanding of the situation and apologized.

However, when I considered returning to my table I felt very uncomfortable that THE(ONLY) server would be responsible for collecting my order from the kitchen and bringing it to my table. I didn't want to be placed in this situation, so I advised the front desk representative that I would not be taking breakfast in the restaurant, today or tomorrow, and I would raise this 'episode' with the manager later in the day when I returned to the hotel.

I have no idea why the server had this issue with me, the voucher, or 'SUBSTITUTIONS'. But I thought it best that I have breakfast somewhere else.

Based on my interaction with this server, I can't recommend eating at this restaurant. Staff & training are obviously a...

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...

We had reservations for 6 at 5:00pm on a Saturday...a little early, but we were going to the 2GNC Comedy Show at 7:00, so we thought casual dining with good conversation before hand with plenty of time. Online it appeared they had a great, diverse menu and wonderful wine/beer selections, so we were all excited. We got there and it was empty...but it filled up not too long after, so no big deal there. The waiter greeted us with a very professional demeanor. Good start. Unfortunately we didn’t know we could only order from a special, Valentine’s menu - that was not well advertised on the website. It was a little expensive, but okay, we got through that. It was a 3 course meal - starter (salad), main meal (I chose filet), and dessert. It was $150 per couple, and included 2 glasses of wine. None of our husbands drink wine, strike 2, but we opted for the girls to drink the wine and the boys ordered beers (at an extra charge - no biggie). Let me skip ahead...it was 7:10 and we still hadn’t gotten our dessert, they had to box it up (after we asked twice and then it still came to the table plated). The bill didn’t include the beer. The waiter was then going to go back and fix it. We were supposed to be at the theater by 7:00, it’s now 7:15...and we were walking there. He came back with the bills and cards and said he couldn’t fix it so the beer was on him. I did appreciate that. We just couldn’t believe that it took over 2 hours to actually get 2 out of the 3 courses of food. It was like our server was the bartender, the cook and the waiter all at the same time. He was always polite and professional and I know he was probably frustrated with us at the end since we were rushing him because we had to leave. I didn’t think at 5:00 we’d have to warn that we would need to leave by 7:00. So I thought the food was great - 4 of us ordered the filet and ordered them medium rare (me!), medium and two well-done, and they all turned out perfectly. Kudos on the steak! The mashed potatoes were so tasty...my family LOVES mine and I thought these were stiff competition. The boxed up desserts were destroyed by 4 teenagers when we got home from the concert, so not sure if they were good or they were hungry. The wine choices again were awesome for someone that appreciates good wine. I would consider going back for wine and apps, but I haven’t read great reviews about the loft section of the restaurant, so not sure I’d go out of my way to go back unless I was already downtown in that area for another reason. The atmosphere is pretty neat...the bar is cool...the upstairs would be ideal to hang out (add more comfy seating, instead of dining tables/chairs)...the wine selections are high end. All in all, I’d...