Dear Annie has a great atmosphere and an impressive selection of wines, but I don't recommend coming for the food. Last time I visited, I ordered their "Sea Dog" which they purport to be their special dish. I should have thought twice when the server told me it was "creamy," but they had a limited selection of food and I was very hungry--and, they made it seem like their signature dish! When it came, I immediately realized I had made a terrible mistake. One bite of the Sea Dog was all I could manage, as it was, in fact, very creamy, and very fishy. It was a very unpleasant eating experience, and I actually sent it back, which I almost never do. I will take some responsibility for ordering this dish, but I'm still puzzled by the whole thing. It was like creamy, fishy seafood mush enclosed in a sausage casing. The server did kindly offer to take it off our bill which I appreciated. On the bright side, the staff was very helpful and I really enjoyed the wine they recommended. I'd gladly come back for wine and the pleasant ambiance, but after the Sea Dog incident I'll probably stay away from their food for the most part. read more

Dear Annie - Sea Dog - Wine Bars Near Me - Cambridge, Massachusetts

They no longer add the automatic 25% gratuity! Yay :) The atmosphere at Dear Annie is exquisite and they have a nice selection of wines. I haven't personally tried their food, but my friend had the grilled cheese and thought it was great! This is a perfect spot for a girls' night, a date, or just to hang with a group of friends! I will say it's a bit tough being expected to tip 25% on an entire bottle of wine...although they no longer add the automatic gratuity, they have multiple signs encouraging people to tip and I did feel some type of way after we did not tip the full 25% on a bottle. The workers behind the counter aren't very welcoming or friendly and I did feel a bit judged for not tipping the full 25%. Hoping it was just in my head but it honestly didn't feel great. I hope they can work on their service because this place has amazing potential. read more

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Dear Annie always caught my eye on the street, and I was finally able to make a reservation for a girls night. Such a cute and cozy wine lounge that was busy even on a Tuesday night. Their wine selection was great and the girls at the counter had great recs. Shared the fish of the day with brussel sprouts, grilled cheese, and mussels which were all pretty good with moderate portions. We were able to get 1/2 off oysters which were really big and came with a wonderful vinaigrette. read more

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The ambiance was *chefs kisses. Probably my new favorite location to catch up with the girls. They have a wide variety of wine selections and small bites read more

Dear Annie - Vibe - Wine Bars Near Me - Cambridge, Massachusetts

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This place is so cute and chic! I went here with 2 friends and sat inside. There is a vast amount of different wines to choose from and the service is great and they are able to describe all of the different wines so customers are able to choose to their liking. Since this place is more of a wine bar vibe and they don't have large plates for food instead they have more of snacks and small bites which are tasty. Definitely a place to try out if you're a wine person! read more

I really enjoy Dear Annie. I've come twice and both times sat outside which is a lovely little patio on the sidewalk. Very casual while still feeling proper tidy - their wine selection is unique and uplifting, the small bites are eclectic and yummy though a little tough if you need modifications. The service is very kind, easy going and welcoming. Definitely recommend for an easy meetup spot or spontaneous special treat! The inside decor is chic and fun as well with curious kitchen collections! read more

Dear Annie - Side by side the two oranges of the season - Wine Bars Near Me - Cambridge, Massachusetts

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Dear Annie is a fine natural wine bar with a cozy ambiance, though I do understand where several of the past reviews come from. As a disclaimer, we (party of 2) did not order any food while we were at Dear Annie. We came in on a Saturday evening around 5pm for a bit over an hour. We were promptly seated by the window. The ambiance inside is cozy, and the wall of wine bottles and overall living room vibe felt nice, especially given that the day we went was quite rainy. We ordered two glasses of wine total: a 2021 Sangiovese and a 2021 Sauvignon Blanc. During this service, in which we order at the front of the bar, the server gave us a tasting sip before we committed to the glass. The wines themselves were also good, and were similar to those I've enjoyed at similar natural wine bars in California. The reason that this is not 5 stars: it simply felt too expensive. The prices of the glasses themselves are on par with what you see these days at local restaurants serving natural wine (e.g. Toro and Coppa in the South End), but the auto ~23% gratuity just felt like too much. With all fees included, our total bill came to $40+ for just two drinks over a bit over an hour. For what we got, it just felt like too much. I'm not writing off Dear Annie by any means, and I may be back in the future. Overall, it's a fine natural wine bar. read more

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They add 23% gratuities to bill And have a line for additional tip! I didn't notice and tipped twice $2.00 for butter and oil for the side order of bread! Cheese Board was pathetic. Beware. For me I chalk it up to LIVE AND LEARN. read more

Way too expensive; the auto ~20% gratuity also put a sour taste in my mouth for the minimal and borderline rude service. It's a shame because I like a good wine bar that serves snacks for those nights you want something relatively small to go with your drink but I left feeling utterly robbed. Dear Annie is very much a cafe charging steakhouse prices. - Exhibit A: $5 for HALF of a deviled egg. Come on. I know there's a nation-wide shortage of eggs and also that egg happened to be the best thing we ordered, but that price tag is absurd. - Exhibit B: A tiny platter of roasted carrots was $15. - Exhibit C: A tiny bowl of beans, $16. I guess I don't need to recite the menu (and of course, I could have taken a look at it beforehand and suggested somewhere else). Honestly, the way the dishes were priced, it almost felt like they were hoping people wouldn't be paying too much attention to how much they were spending as they got wine-drunk. Speaking of the service. There's too little service except for someone bringing the food to your table to warrant such a steep auto gratuity. When I went up to the counter to order a second glass and asked if I could try a little from a bottle, the lady acted like I was doing her a favor. Really cold and standoffish and didn't ask if I liked it, what my preferences were, no recommendations, etc. - you know, none of the standard customer service questions that would be asked at a WINE BAR. She basically stood there and stared at me as I was trying to decide. Super uncomfortable. I'm never coming back and I wouldn't recommend it. read more

The coziest spot to have a glass of wine on a cold day. Such a pleasant experience, I can't understand why it has such low ratings. Would happily go again! read more

Dear Annie - Wine Bars Near Me - Cambridge, Massachusetts

Dear Annie is the sister resto of Rebel Rebel (a James Beard nominated for its wine program), so I decided to check them out because I wanted food to go with my wine. The long table is community style seating and there are little tables along the walls to seat groups of 1-4 people. There's also a lovely outdoor patio with additional seating. You won't have a dedicated server, you will have to order your food and wine at the counter/bar. Although, it's a wine bar if you are wanting food and lean more towards the carnivore side, this place might not be for you. It's gears more towards fish and vegetables. I ordered the kimchi deviled eggs, oysters (with a cucumber mimotte), and the fish of the day (which was a poached cod). I loved all of my chooses and with the help of the server, all completed each other well. For me, the house made hot sauce was the star of the deviled eggs. Oysters were lovely and I think there was some white pepper to make the cucumber mimotte stand out from others. If you are a person who looks for more comforting food and are not adventurous eater this place might not be for you. I wasn't sure what wine to choose, and the server gave me three options that she believed would pair nicely with all my chooses. And they do have interesting chooses like a rosé that could fool you for a light red, but I ultimately chose the orange (and went back later for the rosé). There is a 23% gratuity automatically added to each bill (20% for front of house tip and 3% -if you order food- for back of house). For those that grumble about not having a server and still paying 20% ... hear me out. My 20% tip went to my servers knowledge on the wine she was selling and helped me decide on based on my preferences. Honestly, 3% is little for home much back of the house busts their asses to provide service in the form of food. And I would know, since I've worked with a James Beard nominated chef in the back of the house. read more

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Dear Annie had been on my list to try for a while after it made some of the local hot restaurant lists a few years back. Unfortunately, it did not live up to expectations. The food was good, but not especially notable, and priced excessively even by Boston standards. The fish tacos, $9 each, and deviled eggs, $5 per HALF egg, were tasty but certainly not special enough to merit the price tag. The space was cute but very casual and not especially comfortable - giving hip coffee shop energy rather than charming restaurant or wine bar as I had hoped. The restaurant is also not full service - guests have to order food and wine at a counter, get their own utensils and water, and the menu descriptions are written on a chalkboard in the corner of the restaurant so you either have to ask the staff to describe every item on the paper menu (which just lists general terms like 'seasonal salad') or walk across the restaurant and read off a wall. To top it off, there is an obligatory 23% added to the bill. While this is in lieu of tip, it felt like one last insult to injury given how over-priced the food already was and that they do not even have full table service. Eating out is one of my great joys and I am happy to spend more for a memorable dining experience but the balance of cost to quality and service at Dear Annie was just way off for me. While I could potentially recommend for a glass of wine and a snack with a friend, I would not recommend for dinner. My partner and I left dissatisfied and almost $200 in the hole... read more

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The server at the register is so rude and condescending that it ruined my whole experience. I've never felt so uncomfortable or unwelcome at an establishment. She acted like I was a moron when I didn't bring back our used wine classes to order a different wine. I figured they would give us new glasses since we were getting a different wine. It's like anything I said pained her. I rarely complain about service, since I respect the hard work of anyone in the service industry but this was next level. read more

I would never go back to this place. the food was delicious, but crazy overpriced, super chintzy servings, worst acoustics I have ever experienced in a restaurant (not kidding), and after you do your own service - going up and ordering at the bar, bringing your own glasses and silverware to the table - they tack on 23% of your bill for service!?? too old for this shit, can cook for myself without the aggravation in read more

I didn't read the reviews before I went, but I, too, was appalled at the 23% gratuity. I don't mind paying a tip when there is actual service. But, my date and I entered, sat down (on uncomfortable stools), were handed menus and told that we needed to go up to the counter to order our drinks. We walked up to the counter, they poured the wine, put the glasses on the counter, and we had to carry our drinks back to the table. What exactly was the service we were paying for? 23% is high for a tip anyway unless there is great service. I liked the ambiance (though not the uncomfortable chairs), but definitely won't be going back due to the unexplained gratuity. read more

Great spot, great food, amazing wine selection. I love the ambiance of this place, great spot to have a glass of wine, chill, hang low, eat a ton of food, have a chat. It has a very local, communal vibe that's hard to find in cities these days. The staff are always so cool, with a lot of wonderful experiences/ wine knowledge to share. Their oysters are out of control... it's just a good damn spot. read more

Stay away from this place. The service is terrible. When we asked about the different wines on the menu we were just told that they were listed from light to full bodied and which ones were pink and orange. Given that this was a wine bar with unique wines, we expected some tasting notes and a more educational experience. A 23% gratuity was also included automatically despite the lack of service. read more

Incredibly rude woman behind the bar -- not overt, but that quiet, under-the-breath hostility that makes you feel unwelcome the moment you walk in. The whole place has a strangely arrogant vibe. The seating is uncomfortable and if you're outside, be prepared for a floppy fabric awning to hit you in the face. Most tables are awkwardly low for eating unless you squeeze into a communal one. The food? It's fine. Nothing special. Certainly not enough to justify the atmosphere. And here's the kicker: despite there being no table service (you order at the register), they automatically add a 23% gratuity. It just leaves a bad taste. Not coming back. read more

I've been wanting to try this place for so long! it's in the middle of Harvard square and porter square, worth the walk! It's a small cute place, communal seating dim lighting perfect for a date night. There were a lot of wine choices and the staff are super helpful in making a decision on which glass to pick. They even let me try the wine before making the decision. Not pictured: the cheese board which didn't come with as much cheese as I thought but still delicious read more

Dear Annie - Menu - Wine Bars Near Me - Cambridge, Massachusetts

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Went on Valentine's Day without a reservation close to opening and felt lucky to get a seat! The inside of Dear Annie is beautiful and the layout is very cozy. Enjoyed some of their rotating food - the grilled cheese was amazing. Enjoyed our wine selections but the bartenders seemed a bit too busy and overwhelmed to really help us choose the best pours for us. Would want to come back at a less busy time for a full and better experience. read more

I was pretty amazed at the low star ratings for this spot, but I can't say I disagree with the thoughts shared about uncomfortable seating and inflated prices. That said, we were aware we'd be spending too much money coming in and went for a bottle of wine, two apps, and two entrees which set us back about $240. Everything was really good. Will I ever go back? No, I could eat so much more food for $240 and we had to go get French fries after because we were still hungry. Despite that, I had good service and I really enjoyed everything that I tried here (fish sausage, marinated fish, oysters, olives, etc.). I thought it was great and if dropping $240 is not a big thing for you I'd definitely recommend it. The fish sausage was definitely the stand out item for us. read more

The positives- really nice staff, cool vibe and decor, communal table The negative- the food was horrible It would be great if they offered some basic, decent dishes. Maybe just go for a glass of wine there and then move on to somewhere else for dinner? read more

The 3 star overall rating for Dear Annie is way off base. It really doesn't reflect the food, the ambiance, or the service. Instead, it reflects the people who are upset about the food prices, and the order-at-the-counter style. Granted, I've only been here once a few weeks ago-- but I have reservations booked for again later this month. On my first visit, the service was fantastic-- I don't remember anyone's names, but the woman pouring wine at the counter took ample time to help my friend find a wine she liked. The place was full but she didn't rush my friend at all. And the other two women working there were super friendly and struck up light conversation with me throughout the night. The food was delicious (we went on a taco night). The tacos were a proper size (3 was good for me). The wine list was fantastically curated, though I wish there were more by-the-glass options. The ambiance was nice : I'm not a huge fan of communal seating but there are also a few side tables. Our communal neighbors asked us about the wines we had and they ended up ordering (and loving) the one I recommended. We chatted a bit but they weren't intrusive . The wine was good, the lights were moody, and overall we had a great time -- which is why I'll be back. I get that folks are tired of stuff outside costing soooo much money. But the same goes for bars/restaurants. The overhead prices are rising and EVERYONE is paying more. Yes, $20 for 2 whole eggs is crazy. I agree. But if that's too steep then, order something else that's a better value -- like one of the entrees that are also around $20 and are more satisfying than eating two eggs. No one is being forced to purchase anything. I don't know what else to tell you.... As for the automatic gratuity without "service"--- tell that to the back of the house busting their asses every night to cook, clean, and wash dishes by hand. This is a once-in-awhile spot for me because of the bougie prices. You're either with it or you're not; but don't trash the place or give low ratings simply because you can't afford it. read more

This place could use a more balanced review since it seems everyone else either loves it or hates it. Tl;dr it's expensive but on the whole worth it, so let's say 3.75 stars. Our food was very good. The marinated squid and the chocolate tart (which comes with miso whipped cream -- very interesting) in particular were superb. We also had the deviled egg and the monkfish which were delicious as well. No complaints about the quality or taste of the food. The ambiance is great, chill vibes, cozy, artsy. We went early when the place was bathed in light and not too busy, that probably helped. I think it's nicer inside than outside. Other reviewers don't like the 23% service charge, given that the servers don't seem to do much. But if you approach the place as a cafe that has wine, gourmet food, and servers to bring you your food and bus your plates at the end, rather than as a restaurant that forces you to order at a counter, it's not such a big deal. To be honest, I wish more restaurants would let you just grab water, a napkin, or a sharing plate when you want, instead of needing to wait around for someone to bring it to you. Yeah 23% gratuity is a little steep considering, but there's no obligation to give more (counter to what some others have said), and it's in line with other restaurants these days. All that said, yes, it is a pricey place. The drinks in particular are quite expensive. Not just wine, but also non-alcoholic beer and cider are in the $15+ range. That makes it prohibitive to have more than one or two drinks. Some food portions are small for the price: the deviled egg is only half an egg, which bothers me because if I pay $5 for an egg, I'd better get a whole egg. And the monkfish, while tasty, is a pretty modest portion considering it's the priciest thing on the menu. The dessert, however, was surprisingly generous for the $10 price and very shareable. All in all, I would return. They are playing a dangerous game, being right on the line of "pricey but worth it" and "Jesus this place is expensive." But I found the high quality of the food, the good vibes, and the pleasant service combined just about justified the price. read more

Dear Annie - Squid and cod "not tinned fish" - Wine Bars Near Me - Cambridge, Massachusetts

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Atmosphere is nice. Wine descent. 23% gratuity tip when you have to serve yourself including getting your own napkins diffidently needs to change. read more

I came here after walking out of The Abbey a few doors down. Dear Annie was the closest bar walking distance and it was such a win. The chill/cozy/chic vibe was exactly what we were looking for. Once walking in it was a given Dear Annie is pricier than the surrounding bars/restaurants. It felt cozier, looked nicer, flowers everywhere, perfect lighting, a wall of wines, music not too loud not too soft, not to mention the patrons there were dressed superbly. (I like to think i blended right in). You get what you pay for. The women that helped us were very friendly and had good recommendations of what to drink. I like trying the employee favorites and they were a win. I'll definitely be coming back and will recommend to friends and family. read more

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We didn't order food so my comments are just about the wine, and they echo a lot of what's already been said. - Though friendly, the service is minimal. You order at the bar and serve yourself. Hard to understand the automatic 23% gratuity. They should just bake that into the cost of the wine, though I wonder if they don't do so because the price of the wine is already steep. - We asked for dry white wines and wound up with two glasses that were both too sweet for our liking. In hindsight, I guess we should've specified dry AND not sweet, but it was still disappointing to pay $40 for two (small) glasses of wine that neither one of us enjoyed. Now to balance things out, some positives: - The ambiance is nice. The interior feels warm and communal. And though a bit stark, outdoor seating is always a plus. - The service is friendly. Overall, I wanted to like this spot, but unfortunately I don't see myself going back. read more

This is a cute date spot or place to catch up with a friend. It is definitely a small spot that's very intimate inside. I think coming in with the mindset of a small bar makes this place stand out from other places. This isn't a large bar that you can come into with a large group. It is perfect for a date or even coming by yourself. The staff are friendly and very knowledgeable about their wines. They let me taste a few of their rec commendations before choosing one to stick with. For food, I believe they are all pescatarian friendly finger foods. We got the squash and it was very tasty! read more

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23% required tip and there is no waiter. Orders and payment must be done at the counter. We spent $200 on 4 glasses of wine and 4 snacks. I would not recommend based on the price, portions, or service. Cafe ambiance with steakhouse prices. read more

Nice wine bar offering a large selection of wines in a casual atmosphere with communal seating. Dear Annie offers a large variety of wines. I ordered at the bar and brought our glasses of wine to a table. We chatted, relaxed and enjoyed our wines. By the time we left, the tables inside and outside were full of people enjoy the evening. Dear Annie offers wines and small bites. There is an automatic service and kitchen fee, but I liked the casual atmosphere and we enjoyed our evening. read more

Dear Annie - Wine Bars Near Me - Cambridge, Massachusetts

I came here in the summer and sat outdoors - which was such a cute spot to people watch in Cambridge! Dear Annie has a lovely wine selection, and the staff was very knowledgeable in helping us decide what wines to ordered. We also ordered the green beans as an appetizer which were so delicious- well seasoned and in an amazing homemade sauce. read more

Dear Annie - Green Beans - Wine Bars Near Me - Cambridge, Massachusetts

Aesthetic 10/10 Food 6/10 Wine selection 7.5/10 Service 8/10 Please note that if you choose to dine inside, you will need to show proof of vaccination. Otherwise, there is outside seating available. No reservations so first come first serve but came in on a Saturday from 5-7:30pm and there was plenty of seating available. You will go up to put your wine and food order in and then find seating afterwards. You also grab your own utensils, napkins, and plates as necessary. Loved the cute, airy and quaint vibes as the weather starts to get nice in Boston. The food was pretty mediocre. Not very flavorful. Note that there's a service charge already included of 23%. read more

Dear Annie - Wine Bars Near Me - Cambridge, Massachusetts

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This place makes me angry. The food and wine are ridiculously overpriced for being so mediocre. The seating is uncomfortable and there's a draft from the door. But the thing that gets me the most is there's a 20% hospitality fee added to the bill (and yet you have to order at a counter and get your own water and dishes) yet there's only a 3% kitchen fee. Why do the kitchen staff (who were the only people of color in the entire restaurant) get so much less?? I will not be returning. read more

Such a lovely spot with a local neighborhood feel! Lots of reviews about the price / 20% service fee which I understand...def was pricy for 3 dishes but we had a glass of wine each which was very nice and the staff are all very nice and knowledgeable so I'm happy to pay a little extra for such a pleasant experience !! read more

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Pretentious. Entered with no greeting from staff...Added a mandatory 25% tip, and had to go up to counter and order and ...they had the the nerve to ask me if I'd like to add an additional tip; I almost admire the ballsiness, but seriously?!? Limited menu. Food ok, but not worth the obnoxious prices. So exclusive and trendy that they have no phone number and no sign out front...ooooohh!! Sat on 18" stools w wobbly tiny table. Curiously asked one of the waiter/cashiers who the lady was pictured with David Bowie and Keith Richards on the cover of their menu... he dismissively replied "that's Iman, Bowie's wife", like how could I not know that?!...looked the picture up later, and it was Tina Turner lol (see attached) Save your money. I wish I read the other reviews bc the owners obviously have relatives reviewing them for the NYT and Bon Appetit. read more

Dear Annie - Wine Bars Near Me - Cambridge, Massachusetts

This is a perfectly curated spot from the welcoming vibes to the tasty food menu and extensive wine list.

Came by on a Sunday afternoon as the sun was setting and found the space to be really cozy and lovely. A lot of plants, natural light, and the walls are adorned with art and countless bottles of wine to choose from. A few folks in our party got bottles whereas others got wine by the glass. We enjoyed them all and the folks who worked here were more than happy to offer samples to help us make a selection. We also ordered the cheese board and the sweet potato panini - all tasty. The wines run about $15 a glass. The space was filled with groups of friends catching up as well as a number of ?first dates. It's a very cute spot, certainly romantic, but maybe not ideal if you're looking for privacy or quiet. The seating is more communal and open. Overall, would recommend! read more

Kind of amazing. Nothing like it in this part of the city. Expect a no-service wine bar w/ great vibe, communal atmosphere, experimental wines, surprising small touches and morsels. Come to chill + be part of the crowd, whoever is there that evening. Relax. Don't come for a full meal, or if you're anxious about timing. They don't do reservations for a reason; you can see how busy it is when you walk in. You won't be catered to by waiters; you also won't be pressured to finish up and move on. An ideal place to sit outside with a friend and, when the spirit moves you, go chat with a sommelier. read more

Comically terrible. We rushed to get here when the restaurant opened at 5pm, as the space is small and they don't take reservations. Arrived 15 minutes after opening and the one (1) communal indoor table was fully occupied, including one guy who had his MacBook out as though he was lounging at a Starbucks. The hostess told us we could sit outside and she'd bring us inside if something opened up, though we never saw her again. She brought us to a table, dropped off two menus (for our party of four), and then promptly disappeared. We sat there for several minutes with no staff coming to take our order. It finally dawned on us that we were expected to walk inside to order at the counter. Oh, and pick up our utensils. Weird...? Looking at the menu, it was immediately obvious that the restaurant has no idea what it's trying to be. I guess it's kind of like tapas? But there aren't nearly enough choices compared to an actual tapas restaurant. Dishes are very small and fairly expensive, each one bolstered with the same slice of bread. The $24 cheese plate had four bite-sized slices of cheese. Food was good, but inadequate as a meal. Halfway through dinner, we ordered two grilled cheeses as it became obvious that we'd be starving by the end of this "meal". Overall, this place is confused and confusing. They're not sure if they're a restaurant or a cafe or a wine bar. They're a little bit of all of them, but not successful at any of them. The drinks were very overpriced and the dishes were shockingly small portions. The added gratuity and fees were absurd, as we honestly did half of the work. Totally disappointing. We made burgers when we got home. read more

The prices, tiny portions, snobby service, and tipping policy are INSANE. If this is somehow your definition of fun, have at it. read more