We ended up ubering here from our hotel but there's street parking here in downtown Annapolis. We didn't have to wait and we didn't make a reservation. They were pretty busy and the bar was packed to watch the Kentucky Derby. It was very cute inside and not too loud where you can't have a conversation. It did take a little bit before someone came and greeted us but our server was friendly and another individual (maybe a manager) was consistently helpful throughout the evening. We ordered a bottle of red wine to share and we were asked if we wanted a decanter to which we replied yes. He poured it in at our table with an aerator. For food, I ordered the City Dock Pizza and my friend ordered the Beef Bolognese. The City Dock Pizza was good - thinner crust but plenty of flavor. The Beef Bolognese was a lighter colored sauce than I anticipated. The pasta was good and the sauce was also good but not what I would consider a traditional Bolognese. We did order the Cheesecake and a couple glasses of prosecco and they were sweet enough to put in a candle for my friend's birthday. The cheesecake is DEFINITELY recommended, it was very good and came as a suggestion. It did not disappoint. Overall, had a great time and would definitely come back and everyone was really friendly. read more

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I really enjoyed my time at red red wine bar! It was a pretty quiet Thursday night which gave us time to chat up the bartender! We didn't try any food since we had just come from dinner. It's a cozy vibe inside, their menu has everything from pizza to charcuterie and I'll definitely be back to try their dishes. The espresso martini flight did not disappoint! read more

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Wow! What a great place. I contacted Red, Red Wine when planning a Galentine's Day Happy Hour gathering for our retired womens' group. Lisa replied by email and was very accommodating. When I arrived a bit early, they helped me to set up. Sara was the bartender/server this afternoon, and she did an amazing job of keeping eight different orders straight. Their happy hour drink and food specials are delicious and very reasonable. The daily wine specials were a great value for $5. The individual size crab dip was really yummy, as were the brussel sprouts. I have been planning happy hour events for a year for our group, and this place definitely gets my vote for best Happy Hour around Annapolis. read more

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Update from 2 years ago : I visited this location again, this time for a Culture Caucus Extended Happy Hour event and sadly.. I'm nearly as unimpressed as I was then, now. The reason I've given Red Red Wine Bar an extra star this time, is because the group I came with, one of the fellas ordered a steak with potatoes and a salad (pictured), that he enjoyed, I had their Dock Street pizza and that was better than remembered (also pictured), and their rum punch was so much better this time around. Not sure if I caught the kitchen on a good day or what, but that was better. Now their service, was subpar. There were two bartenders occuping the bar and one was uh, definitely in a better mood than the other. But yes, average at complete most. The decor of the establishment wins again. read more

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Shout to Kelly aka Lisa. One of the best bartenders I have met in a long time. Her skill level is top notch! She is an excellent conversationist. Please go see her and sit at the bar, you won't be disappointed. read more

Annapolis Main Street Food place to try Red Red Wine Bar & Bistro. The service and food was amazing. My waitress was very kind and informative. I want to try more on their New Orleans inspired brunch menu. I want to specifically try their beignets. It's really gorgeous inside, but I prefer to sit outside. read more

I stopped by Red Red Wine Bar for a drink with my husband and in-laws when we were exploring Annapolis for an afternoon and evening a few weeks ago. I had been for events before, but I'd never visited and sat down and ordered off the menu, and I had a nice time! Their wine selection is pretty varied, and the menu had information about the wines to help you choose the wine for you. I tried a couple of white wines, one of which I really enjoyed. Red Red is also a bit of a bottle shop, so I ended up going home with a bottle of Pet-Nat that I'm excited to try soon. The wine bar might feel a little dated, but it's comfortable (there are some TVs at the bar for watching sports as well), and the customer service was really great. (They also have some outside seating, which is really nice on a pretty day!) We didn't eat, so I can't speak to the quality of their food, but we enjoyed spending an hour or so at Red Red Wine Bar. read more

This review is for the steak salad alone! I'm usually not a salad at a restaurant person, but this salad was actually phenomenal. The steak was perfectly seared to be crisp on the outside and not too under or over cooked on the inside (cooked medium). Dressing was a vinaigrette that wasn't overwhelming, and the crispy onions really made a difference. This was just a good salad. Didn't have any drinks but they have an extensive wine collection that would pair nicely with their food menu. Staff was also super patient and helpful! read more

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

I ordered the steak and it came burnt and tasting like it came straight out of the microwave. my friend ordered the grilled Ceasar salad and he lettuce somehow came out burnt. i dont reccomend. They gave us PEPSI instead of coke, without our knowledge or reassurance, also my friend asked for butter for her bread 3 times and the butter came out frozen. DO NOT EAT HERE. 1/10 I would recommend if you hate yoursel! read more

We love coming here when in town! All of the staff are lovely and friendly. Hunter is alway a welcome sight when we walk in the door! Sunday brunch is a MUST and the wine selection is fantastic ! read more

Maybe it was a mistake coming here for a charcuterie board so soon since returning from Paris, but theirs is underwhelming. You select one cheese and I played it safe due to my friend's request. The crostini are too hard, obviously they don't have quality fresh bread and the nuts and craisins average. The server was nice and friendly. read more

Red Red Wine Bar - Cheese board with prosciutto - Wine Bars Near Me - Annapolis, Maryland

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We went in to Red Red Wine Bar for a dessert and specialty coffee after our 36th anniversary dinner at Dry 85. Our bartender, John T had never made the requested Nutty Irishman but went right to work on researching it to make. He used the best ingredients and it was just as it should be, tasty. He made my husband a spicy Bloody Mary and took special care with his as well! My crème brûlée was great and our Anniversary celebration ending was so nice. Thanks John T! read more

Red Red Wine Bar - Spicy Bloody Mary - Wine Bars Near Me - Annapolis, Maryland

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We came here primarily for drinks but order some apps too. The fig and brie pastries were very good. Also the wine flight was fantastic! The waitress was friendly and grabbed our items quickly. Additionally the atmosphere is very lovely. I really love the dark sophisticated feel of the place. read more

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

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The energy is off. I just feel like we inconvenience them with our patronage. As a local, it's just so disappointing. Annapolis needs to combat hate culture but you can feel it loudly here. So sad. read more

The service was wonderful. We sat outside and people watched. I had a flight of reds and found the portion and price to be perfect.

My daughter and I had lunch here while I was visiting for a week. Oh my gosh the risotto was the best I have ever had! I had the scallops with the risotto. I told the owner that it was even better than Gordon Ramsey's "Hell Kitchen" in Las Vegas! The staff was very helpful because we were towing two toddlers as well. Thank you for a wonderful experience!!!! read more

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

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DO NOT GO HERE!!! RACIST, PRETENTIOUS BARTENDER ALERT!!! Service: NEGATIVE 1,000,000!!!!!! We walked in to the bar to grab a quick drink before we drove back home and sat at the bar for well over 10 minutes waiting to be greeted. The bartender walked off, comes back and drops a glass as she's coming back but never once greeted us to say "Hello. Give me one minute to clean this up and I'll be with you," never gave us menus to look at while she cleaned the glass up or anything. Prior to cleaning up the glass, she refilled two guests glasses that were already there, cleaned up the glass and still said nothing (by this time we'd already been sitting for over 15 mins). While she was away from the bar doing whatever she was doing, I had to ask another young lady who looked like a bar back if she was a bartender, she said "not tonight" and I said that we'd been sitting there for a minute and would like some sort of help. She handed us menus at the same time a couple was coming in and sat down beside us and walked off. The bartender returns, still hasn't said hello, gave water to a guest that asked to the left of us and proceeds to greet the couple that just sat down to the right of us, took their orders and still DID. NOT. SAY. ANYTHING. TO. US. As we're getting up to leave, I say "I mean it's crazy we can't get service and we've only been sitting here for 20 minutes but they walk in and are greeted and order taken before us as if we haven't been sitting here all this time." The bartender waits until I'm almost at the front door and yells, "I only had to clean up broken glass....." and something else but I kindly ignored the ignorance and left. THAT EXPERIENCE WAS TOTALLY AND UTTERLY DESPICABLE. THE FACT THAT SHE DIDN'T GRASP HER LACK OF CUSTOMER SERVICE AND THE COMPLETE DISRESPECT OF HER ACTIONS AS WE SAT PATIENTLY WHILE SHE CLEANED UP THE GLASS. A COUPLE COMES IN, THEY'RE ALMOST IMMEDIATELY GREETED, AS WE (TWO AFRICAN AMERICAN WOMEN - THE ONLY AFRICAN AMERICANS IN THE ESTABLISHMENT) STILL SIT LOOKING RIGHT AT YOU AND THE FIRST THING YOU THINK TO DO AS WE QUIETLY AND RESPECTFULLY EXPRESS OUR DISDAIN FOR THE LACK OF SERVICE AND DISRESPECTFUL BEHAVIOR, IS CHOSE TO YELL ACROSS THE BAR. ABSOLUTELY ABSURD!!! NEVER AGAIN!!! read more

Red Red Wine Bar - HORRIFIC SERVICE!!! Don't waste your time...the decor isn't all that great anyway!!!! - Wine Bars Near Me - Annapolis, Maryland

This is a cute place close to the water in Annapolis. They decorate for the holiday season and become a holiday pop up bar, I recommend going inside during the December month. The drinks are great and there are plenty of appetizers and shareable plates. read more

Red Red Wine Bar - Lemon Meringue and Bourbon Jam - yummy drinks! - Wine Bars Near Me - Annapolis, Maryland

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While showing visiting family Annapolis, we stopped in on a whim for wine and ended up staying for dinner. They happily accommodated our large party with no reservation, but it is not that large of a place so I would definitely call ahead if you plan to bring a group. Service was phenomenal, as was the food. I had the baja chicken salad and shared the carne asada pizza. Both I recommend and would try again! I really like how they do their wine flights here, pre-picked for you. I've tried them all & sampled a lot of great wines I usually wouldn't have picked for myself. read more

Red Red Wine Bar - Carne Asada Pizza - Wine Bars Near Me - Annapolis, Maryland

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3rd time in a row over the past year we've had a disappointing time at this place we once loved. Kept coming back because we assumed a rough patch. Was quite empty tonight but food service was very slow - and we were not in a rush. Terrible burger. Re: the "prosciutto" on my cheese plate - all prosciutto is ham, but all ham is not prosciutto. The crostini on the cheese board was unpleasantly hard and crunchy. My Jalapeño Houndog cocktail, which previously was a go-to for me and friends had zero spice. The crab dip and Brussels were tasty, but we paid quite a bit to only have tasty appetizers. Our server was good. read more

I've passed by here several times, always on my way to someplace else. Every time I say that I want to go in there. On February 18th, National Drink Wine Day, seemed like a good time to follow through. I was surprised that there were no specials or even a mention of it being National Drink Wine Day, but I was not going to let that deter me. The bar was completely empty at 1:30/2:00 PM except for one other couple. I guess I just missed the lunch crowd, which was fine by me. The times I have passed by it always looked busy, so I was happy to be able to sit and soak it all in. The atmosphere is a fun bohemian style, casual atmosphere. They have a small but gourmet menu to pair their approximately 35 wines by the glass and 120 by the bottle. I was feeling like a dry rose but didn't see one on the menu. As luck would have it, they just got in a French dry Rose that wasn't on the menu yet. My friend and I ordered two sharables: 1. Crab Dip for $14 with a French baguette. The crab dip was made well; smooth and creamy with a decent amount of crab. The baguette was warm and buttery, deliciously soft on the inside with a little crunch on the outside. 2.Pear Prosciutto flatbread pizza for $12.50, with thinly sliced Bartlett pears, prosciutto, honey, feta, olive oil, and minced garlic. The crust was thin and crispy and the mix of sweet and savory really complimented each other. Overall the atmosphere, service, food and wine get 5 stars. I look forward to my next visit. read more

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Love everything about this place!! Friendly staff, good food, great wine, awesome overall ambiance

The service is always great here, never once had an issue or felt unwelcome. Surprisingly good selection of whiskey for a wine bar. Food is generally pretty solid as well read more

so this place has horrible management. I ate there recently and had an issue with payment because my friend was supposed to Apple Pay me. They ended up calling the police. I was mortified when the police showed up. I manag d to pay my bill. However, the manager kicked me out! I couldn't believe it! with all the great competition that they have when I can go to any restaurant and I chose theirs, shame on them for humiliating me, a paying customer. I will never walk through that door again. They're despicable. read more

Annapolis was packed on Saturday night, without a reservation it was going to be hard to snag seats for two. As it happened, two people sitting outside of Red Red Wine left and we were immediately seated. RRW is one of the few places left with outdoor seating. The service was fantastic. Sarah was engaging and timely. The food was...fine. The draft Chardonnay was good. The appetizer of bacon wrapped beef medallions was misleading. They were steak bites not medallions and four came in a big plate that highlighted how small they were. Tasty but very salty. My partner ordered the chicken southwest salad. The veggie part of the salad was good, had a nice variety of ingredients but was a little heavy on the tortilla strips and light on the avocado. The chicken was not tasty and was tough. Didn't feel like the chicken was a priority. The burger was recommended and was delicious. Perfectly cooked and toppings were good. It came with roasted potatoes and I was thinking steakhouse fries? But they were more like huge breakfast potatoes. Starchy and not tasty. However, we ordered the cilantro pesto cauliflower just to try it and: it was the star of the night. Like, whoever cooked those should get an award. Anyway, nice experience on a beautiful Annapolis evening. Would go again, but would sub the cauliflower for those big taters. I'd also note that the prices here are reasonable and portion sizes generous which is not always the case in DTA. read more

Nice waiters, comfortable space. Perfect place to relax on the Main Street in Annapolis by the Capital. Happy hour can be fun with the house wines being excellent. Crab dip was very good too with the perfect amount of bread. Didn't go any deeper in the menu this time, but will definitely be back. read more

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The ambiance of this place sets it apart. Our meals were very good. The Chardonnay we ordered was going to need to be chilled. And then they said they were out. Weird that they didn't have chilled white wine ready to go. But, it was really no big deal as the wine prices are outrageously good. We opted for wine by the glass and it was great. Food was great. It was a Monday night and maybe those are slow in Annapolis? We were literally one of three tables at 7:30pm. We made reservations and absolutely did not need them. Given that, we thought our server could have been a little more attentive. But, we were there to enjoy the company and not be rushed so it all worked out. It's definitely a place to try! read more

Love it here! Now this is a wine bar. A+ experience. The ambience, the music, the colors...this place was a breath of fresh air. We came here for flights and were excited about trying wines from various countries. I ordered the Message in a Bubble sparkling wine flight: *Marqués de Cáceres Cava - Macabeo Blend - Spain - This one was mi vino favorito. It was crisp, light, and leaned more towards semi-dry. *Tenua Sant'Anna Extra Dry - Prosecco - Italy - This one was okay. Believe them when they say that this prosecco is extra dry. I still enjoyed its uniqueness. *Innocent Bystander - Pink Moscato - Australia - If you like sweet, then this is your wine. I liked this one as well; great taste with the right amount of bubbly. I also ordered a slice of chocolate cake because I was tired of being good. It was deliciously rich and full of fat, just the way I like it. Next to the quality wine, our server was such a highlight. She was very amiable and helpful with directing us in the menu. This was a quick visit, but the next time I come, I would like to have the full experience by trying various food options and their cocktail menu. read more

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

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I came here a few weeks ago for dinner and had a great meal. We didn't have a reservation but only had to wait about a half hour for a Saturday evening seating, which wasn't bad at all. We started with some small plates that were all really delicious. Maryland is known for their crab, so of course the crap dip was out of this world. I also loved the roasted Brussels; they were cooked perfectly and their savory balsamic vinaigrette sauce made the dish even better. For my entree, I ordered the crab melt sandwich which was so good, I'd go back just for that! It was so cheesy with plenty of fresh crab. I don't think I've ever had a crab melt as good as Red Red Wine Bar's, which is high praise! read more

Great place to grab lunch! I guess my usual Annapolis lunch spots are closed on Tuesdays, so I was happy to be able to try something new. Red Red Wine Bar had an abundance of outdoor seating, so it seemed meant to be! Service was fast and attentive. I ordered the crab melt with a side of pasta salad. The pasta salad was light, Mediterranean, and refreshing. The crab melt was good but if anything a bit too heavy--there's a lot of bread, cheese, and bacon. My favorite part were the green tomatoes, yum! I went inside to use the restroom and I was very impressed by the swanky decor. This place really captures a vibe and post-pandemic I'd really love to sit in that big velvet chair sipping some red wine under that chandelier that looks like it's from the Mr. Brightside video. read more

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Average food, friendly staff, good atmosphere here! I got the seasonal steak salad and it was good in taste and portion size. I really like the dressing. My friend got the Baja chicken salad and it was HUGE! I hear the pizza is good here so I need to try that. The staff has always been very kind, patient, and friendly. The food came out pretty quickly and water refills or wine orders are always very quick. It always seems clean inside and there's a lot of seating inside and outside. The music is always good. It's never too loud and it's a great place to just sip and chat and vibe for a couple hours. It's pretty casual so you can dress cute for a wine date or honestly just about whatever you want. The parking situation is a little tricky since it's right on Main Street though. I do wish the inside wasn't as dark inside but I still do like it here. Overall, pretty good experience here. I'll be back to sip and chat with friends for sure. read more

Red Red Wine Bar - Seasonal steak salad - Wine Bars Near Me - Annapolis, Maryland

Our waitress forgot to put in our food order and then said the kitchen was closed and hour after we ordered. She then proceeded to smile and said "guess it's a wine diet!" As if we weren't leaving out dinner with only having a bottle of wine. read more

The food was not good at all. I wanted a simple Cesar salad but it was grilled which means they literally make a salad warm. It was very weird and upsetting I wanted to get some fries and they didn't even have that. The service was fine. The place looked cute as well but the food was so bad. read more

Excellent bar and restaurant. The bartender was pleasant, and went above and beyond in taking care of us. The lemon meringue cocktail was exceptional and because I loved it so much he even took the time to teach me how to make it. We had an excellent experience here. The food was also delicious. This is one of my go to places in Annapolis and will probably be yours as well! read more

Red Red Wine Bar - Lemon meringue cocktail - Wine Bars Near Me - Annapolis, Maryland

In town with family and walking downtown Annapolis and we decided to stop for lunch. While the town was busy this restaurant was not. Got seated immediately. I ordered a steak sandwich with a side if cauliflower. The meals came quickly but my side was missing. I hadn't realized the meal came with a pasta side (which was good). The server apologized that he forgotten to put in the side order. The sandwich was good, not great. Someone in our party ordered a steak salad with the dressing on the side and it was not on the side. The other party member ordered the ceasar salad with chicken and thoughouly enjoyed it. 2 salads and a sandwich for lunch was $65. read more

Went here as a post-dinner, post-walking along the water night cap with three others. We sat down outside and was promptly greeted by a waiter. While I was really excited for the cocktails and the apps, everything was just meh. I didn't care for the jalapeño hound dog as the drink was watered down and without flavor. My basil 76 was decent but didn't have the right balance between the sweet and the sour. Finally the empanadas were just not good. The shells were too thick and dry. The meat inside also was too dry and the side of lime cream didn't have any flavor, again! The saving grace was our server who was really kind and responsive. I would try this place again. We went to a wine bar so perhaps it's not surprising the cocktails weren't that good. The pizzas that other folks got looked good so that would be my next move. Pizza and wine! read more

Love this place!!!!!!!! Great atmosphere. All the workers were so nice, helpful, and friendly! Great selection of wine. Very accommodating when I asked to take meat off of one of the flatbreads. The bruschetta was sooooo tasty! Also, loved that there was outdoor dining! read more

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

A good wine selection. Wine flight is fun, great descriptions, very small portions. (Which is fair for $12) I had the Pear Prosciutto pizza. The pizza tasted like someone took 2 tablespoons of canned minced garlic. Pear and prosciutto flavors were absent. Also felt a tad smaller than 12"--more like 8" in. (Four slices total) Service was good. The bartender who took care of us was juggling a lot, but I couldn't tell because they were on it! The ambiance during the holiday was very well decorated, but felt a bit gimmicky. The reason I gave this 3 stars was because the food was a bit subpar. "Higher end"-Italian bar food. read more

My sister and I stumbled upon this place randomly looking for somewhere to stop for drinks and a quick bite to eat and we were impressed. First, the restaurant itself was cozy and dim-lit. Perfect for a chill evening. Next, the bartender was super friendly and funny. He did a great job of making sure we were taken care of despite having a packed bar. We both love wine and got wine flights - I got the Bulls on Parade (Big Bold Bad A** Reds) and she got the Intriguing Whites (Off the Beaten Path Whites). The written descriptions of the wines were perfect and we enjoyed learning about the wines that we were drinking. The bartender was very knowledgeable about all the wines and even gave us outside recommendations based on the ones we liked. He also gave us a taste of a new wine that they were introducing for the sweet wine lovers, which I am not but my sister is so she liked that one too. Lastly, we both got the Seafood Cobb Salad and it was DELICIOUS! It was huge and we just knew we wouldn't finish it but we couldn't stop. Of course, they did not bring us enough dressing for all of that salad but we asked and they brought us each 2 more ramekins of dressing. The service and food were great. I've been thinking about that salad ever since but want to try other things on the menu so I'll definitely be going back. read more

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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