Sir Winston Wine Loft & Restaurant

Tried them while on a food tour and it was amazing. Had the lobster bisque as well as a meat and potatoes dish. The ambience is very inviting and pleasant in there. A mix of old school with new school. Great place to unwind and have a nice glass of wine and tasty dish to accompany it.

Took my wife and mother here for belated Mother's day dinner and it was great! Checked on by staff often and the signature cocktails my wife and I had were great! They also made an off the menu grilled cheese for my son. Would definitely recommend!

Love the beef tips, wings, mojito, and the red snapper, the dessert was amazing wow! We will be back. Wonderful service and atmosphere

This place was phenomenal. Beautiful interior and really fun atmosphere and the food was AMAZING. The pimento cheese sausage dip appetizer was so good. Couldn’t recommend this enough!! (Sarah our waitress was great)

It wasn't busy which made the experience better It gave us time to enjoy the food and restaurant since it was our first time there. Food was really good & the staff was friendly

Very nice decor and they have a Wonderful staff. Especially the front desk. They're very kind, compassionate, and helpful. Very dog friendly too.

The chef really knows how to make flavors pop. Great atmosphere. Great service. Will definitely be back!

Perfect experience. Funny and helpful staff. Delicious food and drinks. Relaxing atmosphere. 100% will return :)

My first visit and it was amazing!! The build your own bloody Mary bar was a big plus

Excellent experience! We had a small hiccup at first with my service dog but it was quickly corrected and we were treated very well, the manager even brought out water and treats for my dog and we were seated in a comfortable area. Our server was knowledgeable and polite. The food was delicious and beautifully prepared. Will definitely go again!

We celebrated Mother’s Day with Brunch at the Sir Winston located in Hotel Indigo, Winston Salem. The food was delicious, prepared perfectly, the atmosphere was welcoming and the staff could not have been friendlier! We would highly recommend for an everyday lunch or dinner or a special day! We will be back!!

If you're seeking a bartender who combines youthful creativity with expert craftsmanship, look no further. Liliia is a talented young bartender serves up the best espresso martini I've ever had — perfectly balanced, richly flavorful, and exquisitely crafted. Their innovative twists on classic cocktails showcase a true passion for mixology and an eye for detail. Every sip is a decadent experience, and their friendly, engaging personality makes the whole visit memorable. Definitely a must-visit for anyone looking to elevate their night out with exceptional drinks and amazing energy!

Great experience at Sir Winston tonight. The food and drinks were both good. We don’t like a large crowd so the fact that it was mostly empty was great for us. We will certainly go back.

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 !

Had a wonderful brunch experience! Enjoyed a delicious Eggs Benedict at their Sunday Smooth Jazz Brunch, complete with complimentary glass of "Bubbly". The live jazz music was very nice and entertaining. My friends really enjoyed their meal as well. The "bloody mary bar" and the "mimosa bar" added a fun option to customize your drink exactly how you like it! Prices were reasonable, food was delicious, serice was attentive and prompt without rushing, and the music was enjoyable. We'll definitely make a return visit. PS -they also let us know that they do pairings dinners - can't wait to experience one of those in the near future.

Overall I had a good experience here. The entrance is quite odd, there was no host. I went to the hotel check-in and she told me to speak with the bartender for a table; I just sat at the bar. I was the only person there at 10:00am on a Thursday, which could probably be expected. I had the All American Breakfast with over medium eggs, bacon, potatoes and a Bloody Mary. The eggs had runny whites but I can deal with that, the rest of the plate was solid. The Bloody Mary was a respectable 7.5/10 (two olives and a lemon wedge… come on.) I would definitely come back here again… pretty cool spot in downtown Winston!

So we actually went to Winston on a Sunday morning for a brunch pop up in another establishment but we got there at 10 am and the line of 50 people was out the door and down the street. The neighbor suggested we go elsewhere and she suggested here. I was skeptical. There was no one in here except a couple tables. The space was amazing. Really cool and funky with great food related quotes on the walls. The menus came and it looked ok. I went with the Pimento Cheese omelet with potatoes and toast. The tri color chunk potatoes were amazing. The omelet was fantastic. Toast was way above average. Even the coffee was well done. Our server Sarah was so nice and attentive. My neighbor had the avocado toast.

We love the atmosphere of Sir Winston. The staff is friendly and service is usually quick. The food is very good and filling. We got the charcuterie board as an appetizer and the Old Man and the Sea entree. Both were great and they actually got me hooked on pickled okra! I don’t drink but my husband enjoys their cocktails. I usually get a mocktail but find it absurd that they charge you $10 for a skinny mocktail.

First off- really neat place with a cool atmosphere! The staff was very pleasant and welcoming. While their food selection was good and their drinks were very tasty, the prices in relation to what we got were just not congruent. We paid $25 for a salmon dish, but the salmon was small, the rice fairly unflavored and there was only a single piece of bok choy. I wouldn’t have been bothered by the amount of food if it had some very unique flavors or spices, but it seemed to lack that as well.

First visit last weekend:Mark was a great server! Enjoyed the food. Specialized menu may not be for everyone! Drinks are delicious! Great atmosphere!

Really cute hotel! Very beautiful! Food was delicious! I had the flank steak sandwich and the steak was so tender! Very flavorful lunch! Definitely recommend!

Great food presentation with nice quiet ambiance. Customer service is a bit off with greeting, low on workers, new to their experience maybe? Though the food makes up for minor problems of not checking on you or not able to remember to bring back what you have asked for. Food 5/5 perfect! Service can be better ❤️

I missed the menu from March 2023 🥲, they changed majority of the food items, but I tried it anyway. It wasn’t bad at all! I just wasn’t aware of the switch up until I got there. The workers are good. Sometimes, the host/hostess isn’t at the front so the times I visited we were just standing in the front looking lost. The waitresses are wonderful though!

The food was pretty good the portion sizes depending on the entree. The atmosphere was nice, there was a private birthday event going on upstairs & they had enough room to be themselves without being suppressed. Even with children, they were no bother to the parties dining in the main area (myself & friends) The drinks were good! The waiters were a bit slow but very friendly.

Had a 6pm reservation and had to wait about 5 minutes before the gentleman working the valet noticed and assisted. We were then escorted to the bar and told to wait there. Bartender was cool and after getting a drink, I had to ask about getting our table. She wasn’t aware and there was definitely a misunderstanding. We were then sat and ordered our dinner. Arancini was on point! Ordered the Carbonara and Beef Wellington. The Carbonara needed salt and not enough Parmesan. The Beef Wellington was cooked well and I thought there was too much liquid on the bottom. Besides that, our waitress was awesome and we had a great time. Probably wouldn’t return again.

We chose this restaurant because the photos and review looked good on Google. Once we arrived, there was absolutely no one at the restaurant except for another table next to us. The tables were all wobbly and not stable. We had to move 3x to find a stable table. The food was underwhelming. We ordered the fried chicken sandwich, pork quesadilla, and a side of fries. I asked for no cheese in my quesadilla but it came out with this white sauce drizzled on top. It didn't taste good. I would avoid. The fries were really good though. BUT after an hour, we both had stomach issues after eating food from this place. So beware..

Clearly catering to people traveling on expenses. $8 bread service. Not nice enough for a cost to bread service. Portion size was extremely small. Lasagna clearly did not have salt added when cooking the pasta. Piri Chicken was literally a half chicken from an oven smeared with a bland paste. Handling a half chicken covered in paste is not the idea of fine dining. It was clear why the place was empty.

Cute place and decent ambience but the menu online is vastly different once in the restaurant. Place has no theme as the offer Indian to Italian to South American and back to American dishes. We got the Arancini app, and it was so bland we sent it back. The Caesar salad was a joke with option to add chicken.. it looked like someone just plucked leg meat of a $4 rotisserie chicken but upcharged $8 for the 2oz portion. The Espresso martini was the only good part. Thank god we are from out of town and dont run the risk of coming back.

The mimosas were good. You were able to make them yourself and add juice/fruit that you want. The food was slightly bland. I was expecting more especially for the prize. Service was good

Nice atmosphere, smart staff, nice menu. Grilled sea bass filleted upon request or served whole, was delicious, served with roasted potatoes. Water is served no ice but a tray of condiments are graciously offered, including rosemary. The water taste like unfiltered tap that was not nice. The Caesar not special too much dressing with no sound of classic anchovies. Prawns were not deveined. Grilled octopus had no sign or flavor of a grill, the romesco was loose and flavorless, nice garnish with cukes, chickpeas and herbs. Wine flights were reasonable, and enjoyable. I would only drink here, maybe some of the appetizers other than shrimp are okay.🤷‍♀️

It pains me to be negative to Sir Winston. I have eaten here before and all was good. However their Thanksgiving Dinner basically sucked. The appetizer was good, what I would expect from Sir Winston. The Tuna Poke was delicious and the crispy deviled eggs were great! The Poke was a pleasant surprise. The main course arrived 50+ minutes after we ordered. Our server offered to have a / the manger come by but it's Thanksgiving, hardly time sensitive so we declined. When the main course came out we both got Turkey. We got maybe 4oz each and my wife got the roasted autumn vegetables which were supposed to include broccoli according to the server but contained nothing but stems of veggies. I mean looked like a discount bag from a cheap food store. Unappetizing and not worthy of this place. 5 hours ago I knew I'd be back, but as it stands right now, I doubt I'll ever return. I have never said this before in life, but that was a meal worth $40 that I paid $160 for. And that is not hyperbole. Visit downtown Winston, and support the local cuisine....please! But maybe think twice about this place for a special occasion.

We went here on Valentines night and it was not worth the price. They were out of a lot of things and the food was just blah. The customer service was really good but the food is definitely not worth it. We ordered the shrimp linguine and it was VERY watery. We will not be returning to this establishment.

Took a trout, the food was pretty tasteless. The food combination was not the best in my view. Mached potatoes would be great but instead it was something bean like that didn't taste anything. A little pricey (26$)for a dinner with no taste. The dessert was good, pudding.

We’ve been to Sir Winston twice before and both times were excellent. Unfortunately, this time around the food was poor. Our group ordered the lobster bisque, arancini, steak, and several other items which were fine. The bisque was more like a porridge with large chunks of chewy, rubbery lobster. The arancini was stuffed with only white rice without any cheese, lacking flavor. Our friend couldn’t eat his steak since it was so charred on the outside when he asked for medium. To the credit of the restaurant, they refired a new steak but this time it came rare with heavy char on the outside again. We appreciated the staff taking the steak off the bill and the chef coming out speak with us. It wasn’t a busy night so we were surprised by the poor quality of food. The atmosphere and drinks at the bar looked great though.

I've eaten here several times before and have never had an issue with the food. But the experience I had last night was the worst I've ever had and is barely worth the two stars I'm giving. I ordered the lobster bisque, which I wish I took a pic of because it was more like a lobster gravy - it was SO thick, it lacked salt and it also had two massive pieces of claw meat. I was also wondering if somebody forget to order salt for the kitchen? I was there with friends and almost everybody's meal was completely unseasoned. I also ordered the caesar salad that was topped with shaved parm, croutons, and dressing, which is fair, but a friend also ordered the caesar but she got the Kraft sprinkle parm and the dressing was definitely not made in-house. It was like they just tossed the lettuce in mayo and had the nerve to provide anchovies at an upcharge (they should have just used them to make the dressing??) I also added an $11 piece of salmon that was the size of a Duplo block (even though it was the only decently cooked thing that tasted the way it was supposed to). The lasagna probably sat under a broiler for too long, someone else had to send back not one, but TWO filet mignons - the first was terribly overcooked and the second also looked like a.briquette but the inside could've been used to make tartare. I grabbed a brisket quesadilla to take home to my husband, but he said it was nothing but fat. Luckily, the waitress was nice and took it all in stride, the chef apologized about the steak, and my group just laughed about how bad everything was. The food used to be so good, but whatever we had last night underwent no QC and WHY is tikka masala on the menu??

We waited over an hour and a half for our food, which was inconsistent, cold, missing ingredients, and in some cases yuck. They were totally unprepared for the crowd that arrived. Um… it’s parents weekend at Wake. Maybe hire some additional chefs/staff for the weekend?? I hope they are better prepared for graduation weekend in May. To make up for it, they charged us half price for everything and offered us another glass of free champagne, but really just do better and I'd be happy to pay full fare.

Husband & I went here today for brunch while celebrating our anniversary weekend. Upon arrival no one greeted us and no one was at the hostess stand, there were only one other couple eating in the entire restaurant (ghost town). The lady behind the bar completely ignored us. We finally went to the bar and asked the lady what do we need to do to eat here. She tells us to seat ourselves and she will come with menus. Within a few minutes she proceeds to tell us we are in a closed section and to please be seated in the section next to it. We waited 10 minutes for her to even bring us a menu, we considered getting up and leaving (wish we would have). We finally get menus and place our order. My coffee came with a small amount of creamer and no sugars of any sort. My husband had to go track down an employee from the hotel and after the coffee was cold we got sugar (no one ever offered to top the coffee or offered any hot.) the girl disappeared for long periods of time and another staff member from the kitchen brought our food to us. At this point we also didn’t have any water left, no one was anywhere to be found. the food was OK, absolutely nothing to brag about but was OK…..until my husband picked up his last slice of bacon to find a long black hair under it. We found the girl and showed her this, she took the plate and disappeared, didn’t apologize or even come back to the table to explain any sort of resolution. After 15 minutes of waiting with no drink, cold coffee, no food we just asked how we could pay as we had been in there for well over an hour now. She simply asked if we wanted it billed to the room or pay with a card. Pathetic. The worst service I have received in years if not my entire lifetime. I will never return here and as an employee of RJReynolds who is constantly booking reservations for our executives I’ll definitely be removing this location as an option to prevent anyone else from the pure lack of service/accommodations of Sir Winston. After a complete wasted morning attempting to grab a bite to eat we ended up at the Kimpton Cardinal who offered Amazing food & service. Do yourself the favor and just keep walking!!!

I am not one to ever leave reviews, in fact this is my first but this was genuinely one of the worst restaurants I have been to in a while. The server made about 5 mistakes throughout the whole night, and came to visit our table to check on us three times over the span of two hours (the night I went was not a busy night). We didn't get a bottle of water until the last 30 minutes. Nevermind the fact that the food was absolutely horrible. The average price for a dish on this menu was $30 and there were 8 of us and we each got a different dish. All of them were okay to horrible and most of them were warm to cold. I personally got the lasagna and it was $22, and I have had better at a school cafeteria. I am telling you right now, DO NOT GO HERE. It was a horrible experience, save your money.

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 major issue.

SKIP THIS PLACE. Waited over an hour and a half for our food, which was inconsistent, cold, and in some cases yuck. They were totally unprepared for the crowd that arrived. Um… it’s parents weekend at Wake. Maybe hire some additional chefs for the weekend?? Some items were inedible, missing ingredients, etc. Very disappointing and I certainly won’t be back. Very bummed I booked this hotel for graduation instead of the Kimpton. The restaurant needs to up their game in a big way before then.