Really wanted to be able to write an overwhelming positive review of this place. It has SO MUCH POTENTIAL! I'll start with the good-- the decor, service and wine flights. In terms of the bad -- I don't understand how a wine tasting bar like this could not offer a cheese plate and charcuterie board...something that is common at many other places, where you have an option of choosing 3 or 6 cheeses and meats to sample along with the wine flights. There were only 2 of us so the idea of ordering a full sized portion of a particular cheese kind of defeats the purpose of sampling several cheeses with wines. Moving on the the food, I whole-heartedly agree with the other Yelper who said the Cuban sandwich had WAY too much rosemary flavor...I believe the rosemary was in the bread. It was overpowering and not a flavor found in traditional Cuban sandwiches. This could easily be solved by swapping out to a plain bread. read more

Red Red Wine Bar - Big Bold Bad A$$ Reds wine flight - Wine Bars Near Me - Annapolis, Maryland

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Went here last night and the experience wasn't as good as it was when I went the first time. The customer service last night was nothing to brag about. My bf and I waited at the hostess desk for about 30 minutes until someone came from the bar to assist us. Then when the young lady spoke to us she had an attitude. She was rude and didn't greet us and told us the kitchen was closed but we could sit at the bar and have drinks. It says that they're open until 2am online. It's should also state what time the kitchen closes... she then asked very flat if we wanted to stay or not and we told her or not and she directed us to an Asian spot that didn't exist smh... needless to say, I'm not sure I'll be back! read more

Crab dip was great with sweet onions in it. Highly recommend the reisling, pink moscato, and lambrusco if you like sweet wines. Nice quiet atmosphere if you are there on the weekdays for dinner. read more

We came here for a date a few weeks ago and really enjoyed the vibe. We got the baked brie to start which I was excited about but the Brie wasn't evenly cooked - it was half melted and half hard. For entrees we got The Gus flatbread and the Cuban Sandwich. Both were very good though the pork on the Cuban tasted like it had a rosemary rub on it that I didn't care for all that much. Would definitely come here next time we are in town though good is closer to a 3 star we really liked the atmosphere and the staff. read more

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This place rocks. Very good wine selection at reasonable prices. I had the grilled Caesar Salad with Grilled Chicken. Possibly one of the best I ever have experienced. Great service. A good go to for a light meal and wine. read more

Horrible service. The food was okay, but from the moment we got there it was not a good experience. It took 20 minutes to get service. Food that was ordered never came. I'm assuming they were understaffed, but our server never came to check on us the entire time we were there except to drop the check. When we explained we didn't get everything, she just said okay and adjusted the check. An apology and attentive service goes a long way. read more

Stopped in for some drinks and a quick dinner, service was amazing and very fast, they weren't busy at the time. Food wasn't bad at all but wasn't anything to write home about. The crab soup was raved about but honestly was just a very good minestrone with a tiny bit of crab. Wouldn't go back but def not disappointed in our choice! read more

Food was bussin but the serving size was a bit on the smaller side. Good atmosphere though its nice to sit down in here! read more

Red Red Wine Bar - Chicken empanadas and loaded baked potato soup - Wine Bars Near Me - Annapolis, Maryland

We went for happy hour and loved the vibe and service! Great selection of wine and we had an appetizer of baked Brie that was absolutely delicious! Can't wait to go back read more

Wow wow wow. I loved this place. Nice ambiance, amazing cheeses, wonderful wine selection (had a delicious Pino Noir) and friendly staff. I would definitely recommend stopping in! Parking is stress parking but there's a garage not too far away and the rates are super reasonable. Food is slightly on the pricey side, but on par with similar places in this area and worth the price tag as well. I will 100% be back in! read more

The best little restaurant in Annapolis. Amazing wine and the best eats. Can't recommend enough!

Must try place! Especially during the holiday season! They have completely transformed their restaurant for Christmas, the decor inside is so festive and makes the dining experience so fun! Went with a few friends after the annapolis chocolate festival. We loooved their cheese boards, wine flights, and Brussels. My friends also got the burger, caprese sandwich, and pear prosciutto pizza. Everything was awesome! Service was great and our waiter was phenomenal, one of my favorite restaurants in Annapolis! read more

Red Red Wine Bar - Old school wine regions flight - Wine Bars Near Me - Annapolis, Maryland

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Nice little spot for wine and have dinner with friends then head down to the dock to walk off your dinner to be by the water.

As patrons we understand that you are under staff, however; for god sake put your hostess to work as well.. The young guy at the hostess stand yesterday June 26, 2021 around 1pm ET was just standing there the entire time like a guard. He wasn't doing anything but seating patrons (restaurant wasn't busy) while the male and female waiter doing everything in their power to accommodate us. He didn't even buss the table when patrons are done, he was still standing there waiting for the waiters to take care of it. The 2 waiters were so overwhelmed to the point, our waiter got our order wrong and charged the food to a different card. The young guy was no assistance at all throughout all this. Please put all your staff to work when you are under staff, and we understand we are coming out of a pandemic but we still expect good service and food. read more

Bottom Line: More than just a wine bar, they have beer and liquor too and a decent dinner menu, Red Red Wine Bar has comfy seating and décor perfectly fitting for a wine bar. While you can order a wide variety of wines by the glass you can also get a bottle from the retail store and pay a $10 corkage fee. For the non-wine drinkers in your party, they also have a beer on draft and many others in bottles. They have some cocktails too. I was expecting the food to be limited to cheese plates and charcuterie boards but they have a full menu. I was there for happy hour but I can see where this would be a good brunch spot too. Service was friendly and attentive. read more

Red Red Wine Bar - Wine Bars Near Me - Annapolis, Maryland

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Very friendly bartender, team members, and pretty good selection of wine. Wine flights are affordable as are wines by the glass, seating is plentiful and they also have beer and mixed drinks for those who are hanging with wine lovers. Ambience is cool and location right on Main St is accessible. Definitely check it out! read more

We visited the weekend of the boat show. Service was fine given the state of the world and everywhere being short staffed. Loved my seafood pizza but the French onion soup tasted tomato based. read more

If you are looking for a great place to drink and fine dine, start here. This establishment not only has phenomenal staff but also has an excellent menu. When I walked in I was promptly served a drink and given a menu. The selection seems meticulously calculated so there is a drink item to match a menu item. The staff are very friendly, knowledgeable, and overall a great experience. I got the turkey ciabatta and it was amazing. I highly recommend this place! Thank you Hailey, Sara, Grace, Ben, and Aaron! read more

Had a great time at this restaurant. We went in for happy hour and all of the food items are basically about half of original price. We got the crab dip, sangria, and white wine of the day from the happy hour menu. Definitely need more bread with the crab dip, so we had to ask for more. We both ordered the Red Red Wine Burger and it was slightly sweet, yet savory! The patty and toppings proportions were perfect to where you don't have anything falling out. Overall, very delicious! Great wine selection as well. The white sangria I drank was very sweet, which is what I personally prefer. The price for the wine, to include the flights are very reasonable and affordable, especially for being in DTA. read more

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Based on the reviews, I was really excited to try this place but was left a little disappointed. The highlight was the peach and mango sangria- a delight. Unfortunately, our mains came out before the appetizer. The waitress seemed either confused or annoyed that we ask her to cancel it. I had the grilled Caesar salad and the dressing was sweet... not a garlicky cheesy dressing. Left a lot to be desired. This place may be great for a drink but based on my experience I won't be eating there again. read more

Cool little wine bar in downtown Annapolis. Wine was good and so was the service. We didn't really have room for food as we just ate, but the pizza was delicious pretty solid! read more

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This place is amazing. It was packed but was able to get a table thirty minutes later. Our server Millie was attentive, friendly and warm. The wine flights are reasonably priced and the food was delicious. We ordered the steak salad and the steak was tender and flavorful. We also ordered the pizza. Pizza was good but hoped it was a little bigger. We had enough for our table. We each got to taste a slice. The double chocolate cake was okay. I am not much of chocolate fan though. They ran out of the carrot cake. It must have been that good for the cake to run out. All in all, I would come back to red, red wine. It has a romantic vibe and would like to try the other wines and food. read more

Red Red Wine Bar - Wine Bars Near Me - Annapolis, Maryland

I'm not sure if it was the sweet and friendly bartender with a beautiful smile who introduced me to the best Malbec I've ever tasted. Or was it the welcoming hostess who whistled a James Brown tune while he worked. Or was it the garlicky white pizza with lump crab meat and shrimp that was pleasing to my taste buds. Or was it the Trombone Shorty Pandora playlist that was playing in the background that made us want to get up and dance. Maybe it was the combination thereof because not only did we enjoy wine and small bites on a Saturday night but came back the next morning for brunch. I just loved the vibe of this spot. There are certainly more popular eateries on the Annapolis waterfront but after walking around and eating ice cream like the rest of the folks, we settled on Red Red Wine for a nightcap. Bob Marley was on triple play and we were hooked. It wasn't packed but everyone had at least six glasses of wine in front of them and seemed happy -- go figure! The high and wide red upholstered wing back seats set this place off. I really didn't want to write this review because this place is special and I don't want it to become crowded like many other spots nearby. read more

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Let me start with saying that this is a really nice place for a glass of wine. Comfortable bar and space, pleasant staff, good wine selections including some on tap (fun!). So after a number of successful forays for an adult beverage, we thought we'd stop in for lunch. My husband started with Maryland crab soup, which had nice veggies and pieces of crab but was simply - and quite strangely - too sweet to eat. He left most of it. I ordered the chicken and goat cheese empanadas ('filled with spinach, sun dried tomatoes and golden raisins') and they were so disappointingly bland, tasted just like dough fried in oil; I pushed them away after just half of one. My husband had also ordered the seafood Cobb salad but was unable to eat most of it as well due to an overwhelming and unfortunate dressing. We are hoping that this was just a really off day in the kitchen, but the bartender never checked in after the food was delivered, and made no comment when we paid for our food after leaving most of it, so we wonder if this is not unusual. We expect we'll go back, but only to drink. read more

We love this place and always come here whenever we visit Annapolis. Love the wine selection and food! read more

Red Red Wine Bar - White wine flight - Wine Bars Near Me - Annapolis, Maryland

Food is fabulous! Service is exceptional. We dine here often and highly recommend. The atmosphere is casual and very comfortable read more

Red Red Wine Bar - The holiday ambiance at red red wine bar - Wine Bars Near Me - Annapolis, Maryland

Our go-to bar and restaurant here, This visit: a medium-rare cheeseburger, a crab melt sandwich, some wine, all perfect and satisfying portions. Just try the place, your odds are good. read more

Went i a weeknight. Sat by the bar. The host and wait staff was very attentive. Had a salad and it wS just ok. Food was bland from what I tried on a friends plate. Meh. I had a similar meh experience years ago. Parking is tough because it's downtown Annapolis. There is outdoor seating if the weather is good. Ambiance is mixed. The big fuzzy red seat I sat in was not too comfortable. But It was clean. Plates looked very presentable. But meh. read more

Free wi-fi. Outlets. These guys were a savior during the power outage. Comfy oversized (like take up the whole wall) Victorian bench of a couch. Cute little seating areas. Huge bar to accommodate lots of people. Private little skype/TV room to do small wine tastings. Cool chandeliers. Trendy feel. Must've been the folks they brought up from D.C. to design the place. Service was friendly and on it. Where else can you get a 10 layer white cake with peanut butter and chocolate, a salad and a glass of wine in the middle of the afternoon. Big fan, big fan. read more

Red Red Wine Bar - 7 layers of peanut butter chocolate n white cake - Wine Bars Near Me - Annapolis, Maryland

This place is such amazing vibes! Came here after such a disappointing night else where, and Red Red Wine really made our girls night so much better. Aaron is phenomenal Such great service, and attitude. He made us feel right at home and so comfortable. We will definitely be back! read more

Red Red Wine Bar - Wine Bars Near Me - Annapolis, Maryland

We enjoyed a nice dinner outside. Given the name, it's no surprise that the wine menu is pretty extensive. In addition to several glasses of wine, we enjoyed the filet mignon and crab cakes. Both were good, but not phenomenal. The crab cakes were a little dry without the sauce. But they tasted fresh. The steak was good, but unremarkable. The overwhelming flavor was of the peppercorn sauce. I would recommend getting it on the side because it was just too much. Our starter of a cheese plate was delicious. Overall a nice experience. While not a 5-star meal, I would return. read more

Whats not to love - a jumbo over-sized sofa for all friends to sit at, a knowledgable wait staff regarding all wines, a judgement free environment, and great beverages! We stopped in visit from Baltimore to hang out with some college friends. It was about to rain out so we opted to visit inside to be safe. There were tons of people outside sitting and sipping away. It's a really chill and relaxed environment. We walked in, were seated almost immediately, and had a wine list at our face! We knew a lot about the wines on their list but still had some quick questions pertaining to some of them. Some of the wait staff were almost overly-informative. It was really neat though. I got the big bad a** reds flight which was three different reds from very dry, dry, to sweet. Absolutely delicious and definitely came to a whole glass if all were put together. The pours were very generous, thank you! Friends and husband got one glass they knew they would like and enjoyed them as well. Again, the full glass pours were generous. We didn't feel robbed. Overall, 5 stars! Clean, friendly, knowledgeable, and COVID protective! Thank you for a relaxing time. read more

I'm a little disappointed in our experience last night, Monday December 19th. The website advertised a fun holiday event that several of my girlfriends and I chose to add to our festivities last night. We specifically chose this place because of the White Christmas movie and "late dinner" and "mulled wine" notes. When we arrived at just before 9 PM (note the ad says 8pm-12AM) it was clear that the restaurant didn't get the memo. There was no hostess, but we would later discover that's because they were no longer serving dinner (kitchen closed at 9). When we inquired about the event, and specifically mentioned the movie, the sweet lady who did end up confused my seating us went off to "ask about" the movie. We sat for several minutes wondering why we had not received any dinner or drink menus (we had not been informed that the advertised event wasn't actually happening yet). After several minutes a friend went up to the two ladies near the bar to ask if we would be getting menus, and we were told "Oh yes! I was just asking about how to get the movie on." We were brought wine menus and, after a few more moments we asked about dinner menus and that's when we were informed that the kitchen closed at 9! We asked about the event and it was shrugged off with a short "oh I'm sorry" and also a sweet attempt to let us know that most restaurants there close at 9 so good luck in finding a place for dinner. We stated we were aware which is why we selected Red Red Wine on this particular night because of the advertised event. I'm hoping to have an opportunity to try this place, though the fact that the staff was completely unaware of this event, or didn't care, was frustrating at best. read more

Red Red Wine Bar - Screenshot of ad still on website - Wine Bars Near Me - Annapolis, Maryland

While taking a stroll through Historic Annapolis, we came upon Red Red Wine and noted that Happy Hour had just started, so we stopped in. Millie was quick to greet and seat us and kicked up a conversation with us about their special wines for Happy Hour. We made a couple of selections and while there, chatted with her about wine in general. She was fun to chat with, very knowledgeable about wine and their offerings and even offered a nice selection, which we ended up buying from a local, MD winery. While there we checked out their entire wine selection... They offer some really nice flights and decent bottles as well. Prices are fair. They also have a VERY NICE menu loaded with some really appetizing selections for starters and entrees. We tried a pizza and really liked it. The venue is beautiful! Nice, comfy, cozy and perfectly decorated. We will most definitely return for dinner! read more

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Just wanted to give a huge shout out to Lorenza for being the best server ever. Came in last night for the tail end of a date night. Took her up on the advice to get the Polination drink made with mead. So yummy. Got a cheese plate and then asked for another drink. Surprise me. Sweet and fizzy, you know what I like. She comes back with a lavender and blueberry collins made with vodka. Delicious! I'm going to have her surprise me with drinks all the time. Another wonderful night at Red Red Wine. read more

The food was good. Drinks were pretty strong, but okay at least you are giving good pours. BUT our server, Sarah, was the worst server we have ever witnessed. She was extremely unattentive. When we asked for waters to go along with our alcohol, she took a VERY long time to get us waters and then one of them was sprite??? I am not sure if this was on purpose or not because how can you get a table 3 waters and then one person sprite? Once we got our food, she never checked on us, never asked if we were okay or wanted more to drink. We had to ask someone else for our check and then we waited around for 30 mins after getting our check and she still did not come to us to get it. We had to go up to the host stand. I am the first person to give a server the benefit of the doubt since I am and have always been in the service industry, but this was poor service. read more

Just wanted to put this out there! We went in last night for a few drinks with the girls! Our bartender was so rude and not nice to us! i was really disappointed! Won't be going back ! read more

We almost walked past. I'm glad we stopped. We saw that there were a few empty sidewalk tables but we decided to take a walk in. Oh My Goodness-it's a beautiful blend of rustic, sexy and eclectic. I love it. The drinks are strong. The food is delicious. I had the best steak salad I've ever had in my life. IN MY LIFE. My steak was cooked perfectly and the combination of thinly sliced pear and figs-wow! Will I come back? I'm checking my calendar as I type this. read more

Red Red Wine Bar - Wine Bars Near Me - Annapolis, Maryland

I absolutely loved this restaurant. You walk in and they have an entire wall of wine bottles. Then they have the other wall with this beautiful red couch that is as tall as the ceiling. The chairs on the other side of the table look like you would find them in an old living room. It was so cute. The food was fabulous. I got a cuban sandwich that was bursting with flavor and i loved every bite. My friends had array of other foods and everyone loved their dishes. The creme brulee was also magnificent. I am not a wine drinker but there seemed to be plenty of peple in here having some and i highly recommend you try this spot! read more

We really were excited and wanted so badly to like it. The menu was great and the atmosphere was cozy. But then we got the worst waitress I've seen in years. She clipped the wine glass against my water glass, it shattered and its entire contents (red Zinfandel) spilled all over my dress and soaked down through to my bra and underwear. She just stood there. No apology whatsoever. I had to ask for napkins! I was covered in red wine. All she said was a brief explanation on how the glass shattered. The entire rest of the night was so awkward. She acted like it never happened! It was like she was in denial or just didn't care. No apology. No offer to comp our meal. No offer to pay a cleaning bill. It was so uncomfortable we decided to cut the evening short. Without commentary or an apology, they only comped the flight and one cheese. It is so rude to not apologize for spilling red wine on someone, no matter where it happens! And especially at a restaurant. The fact only a portion of the meal was comped - without any acknowledgement of what happened- was also offensive. Had she just apologized all would have been forgiven. I know I acted shocked when it happened, but I did not yell or raise my voice. I tried to keep my response as light hearted as possible, assuming she felt guilty. Apparently she felt nothing at all. We will never go back read more