Man this place gets a lot of hate here. The pros: it's a unique vibe that isn't that common in boston. It's cosy and communal. Great fun wines that the whole staff is knowledgeable about. Good small bites. But come for the vibe if you want to catch up with a friend or a fun date night, especially as the weather gets cooler. I'm not going to call it con, because these aren't cons. They're about setting expectations - which I think the staff could do a better job of (ok fine this is the con), which is why I'm knocking a star down. You know how when you go to a restaurant and sometimes they ask you if you've dined with them before? And if not they'll explain the idea of like tapas, or prix fixe menus to you? Dear Annie needs an elevator pitch that the whole staff repeats to newcomers. Some things to keep in mind: Don't go with more than 3 other people. Ideal if you went with one. The new accolades via New York Times and bon appetit means that this place is going to be busy for awhile, and it's meant to be cosy so not the best if you show up with a larger group. It's going to be pricier and you can decide if that's worth it or not - their wines average at a $16/17 and they have a mandatory tip of 23% even though you have to grab your own utensils. I assume they pay their staff well, of which I'm all for. Take time to ask their staff about the wines and try before you buy! And oh if you like the food and wine and wish you could try more...just go to field and vine in union square instead... read more

This place is only worth the visit in one case: you are looking to enjoy a glass of wine in an environment that feels like a well-appointed friend's house, and you are ok with your friend's haughty roommates standing about acting like you don't belong. Dress to impress and channel Parisian chilliness to assert your dominance over the snooty staff. The food is bad. The service is bad. The wines are great. But sometimes all this makes for a good night. Just know what you're getting yourself into before stopping by, and if you are hungry for anything more than 3 mediocre olives for $45, be sure to eat elsewhere. read more

I went in with my friend during peak service on a Friday night. We stood in line for maybe 30 minutes but the staff was friendly and gave us periodic updates about our status in line. Once inside, we ordered a couple glasses of wine and two items off the food menu, and then sat at the communal table. The place was at capacity, but I was able to have a conversation with my friend without an issue all while enjoying tasty wine and food. Don't go here expecting that this is a restaurant first - it is not. It's a wine bar that happens to sell small plates from a pescatarian menu. I REPEAT: IT IS A WINE BAR. The staff is very knowledgeable and willing to help you find something you'll enjoy drinking! Some food I've had here so far include the "sea dog" (a seafood sausage on a bun with various toppings), the mushroom grilled cheese, the stone fruit and tomato salad, and the wildflower honey cake. All of the food is so, so good, but I'd say my top two are the honey cake and the sea dog. You need to order at the counter which is at most 20 feet away from you. There may be a line, but it moves quickly. If you're open minded, like supporting local businesses, appreciate a farm fresh menu, and are even remotely interested in wine, you will probably like this place. read more

Everything in miniature. 7 cubes of raw fish (smaller than half my thumb). 4 pieces of turnips sprinkled with powders that taste like chorizo. A "glass of wine" that wasn't half filled in what looked like dessert wine glass (I ordered red, not dessert wine and it seemed like I was paying $17 for 85ml!!). That amounted to $40!! Was automatically charged 23% for tip and "restaurant fee." Ambience is cheap. The room is so noisy you can barely hear the person next to you. If you really love wine and want to treat yourself, do yourself a favor and go to a liquor store and buy yourself an Amarone. I understand times are hard during covid but this is a joke. I never felt so scammed. read more

Dear Annie - Everything in miniature. The plate is as big as my hand. This was $40! - Wine Bars Near Me - Cambridge, Massachusetts

Cute decor, helpful service, good wine! Will return to try the food which based on the menu looks great

I was hoping to rate this place 4-5 stars, but they lacked a lot of things that I look for in a wine bar and/or restaurant. Dear Annie is a new natural wine bar located in Cambridge. It is a collaboration between Rebel & Rebel (located in Somerville) as well as Field & Vine (also located in Cambridge). I was super excited to check this place out because I love wine and being in the business of wine, I was interested in trying some of their natural wines. To start, parking was easy. We were able to find metered street parking across the street. The ambiance is beautiful. Kind of prohibition like to some extent. Very low lights, ambient, with really cool candles on this one big community table. The place is not big, and besides this one large table, they have other seating towards the front and sides of the center. What I liked about this place besides the ambiance was, the bartender or staff will help you choose what wine you want based on what you like. Very similar to Drink, if you have ever been. Some of the wines we chose were good. What I didn't like was 1. not knowing the price of the wines 2. no wine list to order from or see what they have 3. and the friendliness, customer service, hospitality was lacking BIG time. I know this place is fairly new. I know that the location is in a fairly upscale part of Cambridge, but it was very, very pretentious. I also know that we all had to wear masks walking in and we had to present our vaccination cards or a negative test (which I did not mind at all). But, C'mon! What happened to friendliness these days? Where is the WOW factor when you go out to a new place? The whole world is under extreme stress nowadays, not sure what the next day will bring, and when I want to go out and enjoy a nice glass of wine, the last thing I need is attitude. Or, to feel unwelcomed. There are no servers. The menu is small with mostly seafood and the wines are expensive. And, you don't know how much you're paying until you get your bill or are ready to close out. For 4 glasses of wine (each about $15), it came to a whopping $79 including tip. Yes, they tack on a 23% gratuity for BOH and FOH. If I had a bad experience the first time, I usually give it another try. Dear Annie, I am hoping my second time will be better than my first one. Cheers!! read more

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Service was non existent ...as in self serve with a built in gratuity... with a very rude attitude to boot & food horribly overpriced . If you want to waste & money this is the place to take a first date complete with exhaust from Mass Ave... read more

Annie, are you okay? Are you okay, Annie? Cuz' you're a "smooth criminal." Seriously, after reading all of the negative Yelp reviews, I thought I braced myself for the experience but I was not. Tonight, I patroned this restaurant as my dear friend has wanted to attend this place for years now. This week, before moving out of the Boston-area, we thought we'd go as her "Bon voyage" meal. It was lacking in every way. The food was unexceptional and limp. I would have had no issue paying the amount I was charged for an exceptional meal but it wasn't even good. Just lame and uninspired. Portions were shockingly small. The wines I tasted and I tasted all of the reds offered by the glass, were not good AT ALL. The cheap IKEA patio furniture and melamine plates the food is served on, made the restaurant feel cheap and a money grab. Servers were friendly though a bit pretentious. As my party was seated near the door, we watched patrons and servers alike struggle to enter and exit the establishment to tend to patrons in the outdoor eating area, precariously carrying glasses of wine, plates and cutlery. Nothing about this experience felt special. None of the food or wine was interesting. I don't mind paying the included gratuity, I do mind paying the +250 for the two glasses of wine and the subpar food. I would never do this again and I would never recommend this place. Most telling, after leaving the restaurant, I saw two of the groups who were seated next to my group eating at a near by taqueria. read more

Fantastic wines, and great ambiance. A really cute place to go for some wine tasting. But this place is expensive. The wines are reasonable enough but the food costs and arm and a leg for no reason. The food isn't bad but it isn't "20 dollars per slice of pizza" good. Eat before you go!!! Just have the wines!!! read more

Dear Annie - Dear Annie's front - Wine Bars Near Me - Cambridge, Massachusetts

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The best part of going to Dear Annie is reading the other negative reviews. They are hilariously spot-on. We arrived at 7:30 on a Monday... their 'Pizza Night'. They don't take reservations but fortunately it wasn't as busy due to it being Monday. Upon entering we followed the small line to the counter where we were told to secure a seat first THEN come up and order. Luckily, there were a few seats available at a communal table. I then got BACK in line while my wife held our seats. After a few minutes of waiting, I got to the counter and saw the menu for the first time. In a rush (there was a growing line behind me), I ordered two glasses of wine, some oysters, and the poached cod. I figured I'd order some additional bites after we had our first round. The wines by the glass were lousy for the $16-$17 price point. The oysters were fresh and the cod was delicious. As we snacked I noticed the line continued to grow. Could I order more food or drinks from the staff clearing the plates? Haha, no. Instead of eating and drinking with my wife, I had to jump in line to order more food. I then waited in line for 20 minutes! When I got to the counter I ordered 2 more glasses of wine and 3 slices of pizza to share. The server said they were out of that wine AND they only had two slices of pizza left. At 8:30. On pizza night! I ordered the two remaining slices (not great) and a bottle of wine ($110 and OK). The people in line behind me were pissed as they were running out of items quickly (as they should be). Several groups left when they couldn't order many items on the menu. This restaurant is in serious need of a front of house manager. If it was this bad on a Monday, Dear Annie would be a nightmare on a Friday or Saturday. The final kick in the nuts was the 23% auto gratuity. We had no wait staff. We had to get our own plates, water, and silverware! WTF is the gratuity for? Save your time and money, there are so many better choices in Boston. read more

The atmosphere, prices, and portion sizes are f*cking bullshit! We got one (1) slice of bread with our cheese board for four, had no service (it's a "self-serve adjacent" place?) and the food was underwhelming at best. Would not recommend. read more

Overpriced, do yourself a favor buy any bottle at Total Wine or Wegman's or Ball Square and get some cheese and meat and you will save 70$+ because the wine at this place is subpar and the cheese dish is laughable small and ridiculously expensive even compared to Madrid tapas. What a joke. read more

I don't know how long they can live off Bon Appetit's Best New Restaurants list, obviously procured from some friendly connection, because this place is no where near worth it. It is not a restaurant, they arrange tiny plates of expensive prepared food. Having to line up to order food at the counter is uncomfortable, and so is the seating. They are enjoying a bit of hype now but those lines to get in won't be there in two months. read more

I agree completely with some of the other less than 5-star reviewers: -- No greeting once we arrived...a note on a chalkboard that you're supposed to see to direct you as the entire staff stands behind the counter looking out at the restaurant without acknowledgement or offerings of help -- Ordering from the bar and waiting for our drinks instead of them being brought to us, yet this is a business offering "service" -- We also had to get our own silverware and plates and water if we wanted/needed it, yet again...service? -- It was extremely noisy as it filled up -- The non-negotiable 23% gratuity added on was absurd considering the amount of "service" we received. And there was a question as to whether we wanted to add MORE! For what??!! --The food was fantastic - hence the 2 stars, but I doubt I will go back. Too pretentious and "woke" for its own good. read more

I loved that Dear Annie was a walk in joint where you could grab a seat at the community table, but now it's almost entirely reservations! I tried to grab a spot at the community table and was told it was reserved and I would have to wait 30 minutes to be sat. On the website it says they hold the majority of their tables for walkins, but there was so many empty seats and it was entirely reserved! Very disappointed. read more

Sorry but this place is waaaack. I have no clue how they landed a spot on the times top 50 list because this place is very overrated. You have to bus your own table, and still they have the audacity to charge a 23% service fee!? For what service? The "waitress" plopped down oysters in front of us and didn't explain what each one was garnished with. The mushroom grilled cheese was meh. Small portions and underwhelming presentation. Basically if IKEA attempted to open a fast casual restaurant, it would look like this I think? But without the IKEA prices. Overall a great disappointment. read more

Very rude and snobbish staff. Uncomfortable chairs. I really wanted to like this place but I will never go back. read more

Dear Annie is a great wine bar! The people who work there are wonderful -- kind and knowledgeable. The food is consistently good and the menu is prepared based on in-season ingredients. Def go for a Seadog! The whole atmosphere of the place is a lot of fun! Their wine list is fun and approachable, and has something for everyone -- your friend who waxes on about pet nats will be as happy as your mom who has a solid relationship with Charles Shaw. Also, this is a great place for a solo glass of wine and a nibble after a long day. read more

Went to Dear Annie on a date night before dinner reservations elsewhere, I would not recommend this place to most people, but it does do some things right and would have an appeal to a few. Atmosphere: Very feminine IKEA chic. Big communal table and low benches with a few pillows and stools along the walls, fresh flowers, pastels. It is certainly an esthetic, but with center table lacking intimacy and wall seating lacking comfort, it was not an inviting place to spend time on a date even though at first glace it very much looks it Staff: Knowledgeable, friendly, but there is not a whole lot of service. Order at the counter, take care of your own utencils, plates, water -- the bill has a 23% service charge built in. I knew about the charge ahead of time and I still feel ripped of. Wine: Some very interesting choices, lesser known but decent wines, things you don't see on every shelf, I was happy with both glasses that I got not a wine connoisseur though, more of a foodie. Food: Excellent bites, the best part of the experience, the only criticism is that as delicious as the house pickled vegetables were, that level of pickle does not match well with any wine. Overall: Poor value for food, wine, and service, you just don't get a lot, not to say that what you do get is not good, a unique feel not easily replicated elsewhere might appeal to some but did not appeal to us. The Abbey next door is whole lot better place to spend your money. read more

A dream in the neighborhood. No reservations. Walk up and enjoy funky unique delicious wines. The team there are incredible - passionate about the wine - friendly - cool - five stars for the team. The food is great - I think a lot better than than field and vine, which is related to them. The sea dog is pretty unique - seafood hot dog. I like the sparkling wines. read more

Came here yesterday evening with a few friends - we had a great experience! I was encouraged to taste a few wines before settling on a glass. We had delicious nibbles as well. Yes, the plates are small, but this is not a restaurant, it's a wine bar people! Like an enoteca in Italy - casual and all about the wine. I would recommend this place as somewhere special and fun to meet friends. Nice ambience inside where you can sit at a large table and meet and chat with other people. Love the communal feeling :) read more

Dear Annie has gotten national raves over the food, and my husband absolutely agrees with that. He adores the food, especially the seafood fumet -- when it's not on the menu, he checks in regularly to find out if it's back. I'm not a big seafood eater, so I recognize that I'm missing out on the appeal of the food. What I can have is fine but it's definitely just a snack. I just find the overall vibe of Dear Annie kind of precious. If you want a table that your knees will go under, you're going to be at the big communal table, which is not a thing I love even when I'm not wondering if the person across the table breathing in my direction has asymptomatic covid. If you want a private table, one of you will be perched awkwardly on a bench with your knees a couple inches above a tiny little table, while the other one shifts awkwardly on a plastic folding chair, a couple inches lower but still definitely not able to get your knees under the table, trying to find a position that allows you to get close enough to the table to reach the food or have a conversation. To eat you'll both be uncomfortably hunched over. For sure they are succeeding at sending the message "you're here to have a glass of wine and a snack and go on your way," in what from the outside maybe passes for "fun, relaxed, unpretentious." When they have outdoor dining, the tables and chairs aren't *great* and if it's around sunset one of you will have the sun directly in your eyes, but at least you don't feel like they're actively making you uncomfortable for the vibes. But yes, I would absolutely tip beyond the service fee, because I'm not a jerk. read more

I've been walking past this wine bar for a long time, observing the set-up and opening of the place. I've peered in the windows on days before it opened, or days it happened to be closed. I've always appreciated and admired the attention to detail from the outside, and finally had the pleasure of siting for wine and bites outside on the patio tonight. My husband and I had two great wines and three small plates, and everything was amazing. The staff was also totally friendly and helpful, acknowledging that they're trying something different here, and I'm all for it. We were there on a Friday night and nearly every seat was filled, which was great to see. If you value food and wine served with intention, you'll fit right in. read more

I was so excited to eat here. I've heard so many positive reviews and the menu looked right up my alley. Unfortunately I will never dine here again. After ordering the tomato and stone fruit salad I saw a live maggot crawling in the salad. I alerted the staff and their response was "oh okay". I then had to proceed paying for a dish we barely touched which automatically included a 20% tip. I get things happen, I find bugs in my salad from the grocery store! But the staff's lack of concern for almost eating a maggot that could have caused severe food poising is alarming. I'm all about supporting local and farm to table businesses but the lack of customer service is what really irks me and will never have me or anyone I know dine here again. read more

I don't know how this restaurant got a good review from the New York times. 23% tip for service and you need to order at the counter and get your own water, cutlery and napkin. This restaurant is distilled pretentiousness. The grilled cheese with mushrooms had virtually no cheese and no mushrooms. Overall I thought it was AWFUL. I am never going back. read more

I came here last Monday with a friend and absolutely loved it! We got here right at opening because we were nervous about getting a table, but we had no problem finding a spot. Once inside, you place your order up at the front for food and drinks, and they bring them out to you. I asked for advice picking out a nice glass of wine, and the staff was very helpful and made a great recommendation that was perfect for me. The food here is also incredible. We got two slices of the pizza, which were fluffy and flavorful. The showstopper was the squash, which had a black garlic spread to dip it in that blew me away and has been one of the most delicious small plates I've had anywhere in the Boston area. I hope someday that Dear Annie offers cooking classes because I'm dying to know their secrets! Overall, vibes were cute and cozy, wine was delicious, and the small plates were phenomenal. I'll definitely be a regular here soon! read more

Y'all. This place. If you're a natural wine geek and love to try new things, highly recommend this place! They are exploring a different service model than some are used to - with the pandemic putting such pressure on the service industry as well as increased prices due to inflation (and other events), it isn't surprising that things look and feel different. Dear Annie has a more European model of hospitality, where it is up to the customer to figure out what they want, pay, etc, but I appreciate not having a server come by every five minutes to ask how my meal is and interrupting my conversations. It's a great place to relax, with no pressure to hurry and pay and get out the door. For some, that might mean a little work, but the payoff is amazing! I had one of the most incredible pinot noir's of my LIFE here, and picked up a bottle to take home. We sampled a few of the small plates, and they were the perfect pairing for the wines. read more

Super snobbish! Zero stars! We entered the bar and were not greeted. Then we were trampled for our vaccine cards and we did not have them handy (may 2022 not as common to carry cards). So we were told we could only sit outside which we asked for anyway because it was a warm night. So we were told to come to the bar to order. But never got a menu? So we went in and got a menu. Then saw the crazy prices and extra 23% tax. Then got side eye from the servers and got right up before even ordering. Why is this place so rude?! Good luck! read more

While this restaurant attempts to be cozy and intimate, the service and attention to guests left much to be desired. No direction is given when you enter the restaurant as to where to go and where to order. Very few staff were present for the number of guests. When trying to figure out how to order food after a 40 min wait for a table, we had to ask multiple people for assistance with very curt and unhelpful responses. The food was good but portions are very small. Food and drinks were incredibly expensive with shockingly high service tax and kitchen fees upwards of 20% that need to be paid multiple times without being informed about (we paid twice!!). I do not recommend going and will not be returning. This place is totally overhyped and I would have preferred a refund and I'm sure after others read this review they will not be going either. Very disappointing establishment in the area. read more

Was visiting town and was looking for a nice place to relax and wine & dine. Stumbled upon Dear Annie and was welcomed with nothing but kindness and tasty treats. It's hard to find a place these days with good bubbles and wine that doesn't obliterate your wallet. Let me tell yea dear Annie has an amazing selection of wine for everyone's budget. Enjoyed a sprite glass of pet nat with some tasty oysters- the staff was incredibly knowledgeable and friendly and will definitely be back when I'm in town again. read more

My boyfriend and I had a wonderful experience at Dear Annie! We shared the smoked bluefish and mushroom panini which were both delicious. The wine was great and the staff were knowledgable and friendly. We loved the cozy atmosphere and will be back soon! read more

Nice neighborhood wine bar! Excellent selection, knowledge staff, and excellent food. A must try for any wine enthusiasts/ pescatarians.

Exquisite food, wonderful and unique wine selection, beautiful atmosphere. Dear Annie feels like one of the first in what I hope is a new wave of fine dining. The structure of ordering at the counter, built in service fee, and self-service water all give Dear Annie an egalitarian feel which makes the food and wine that much better. Highly recommend for a date night or an outing with friends. You will try some foods and wine for the first time, all while feeling relaxed and at ease. read more

if you like paying $14 for a few pieces of lettuce then maybe this is the place for you! 23% gratuity mandatorily included for counter service...nice read more