Dear Annie is a cute wine bar where you can try a variety of different wines. If you are going to have more than 1 glass of wine it is definitely worth it to get a bottle price wise than get a couple single glasses. It can get pretty busy since it is a small establishment. They let us stand and enjoy a glass of wine while waiting for a seat to open up which I thought was very nice. The staff is very friendly and knowledgeable of wine, I enjoyed the wine that was recommended to me. There us no table service - you go to the counter to order which I don’t mind. There is an automatic fee applied to your bill that serves as the tip.
Atmosphere: 4
Service: 4
유선일
Automatically taking 23% tip when they are not even serving wines, waters nor a single napkins or utensils? Ridiculous. They're literally taking orders from counter and don't even bring checks to the table. Which SERVICE are we paying for?
Taylor Cummings
Best atmosphere in Porter Sq…go during golden hour.
Atmosphere: 5
Katherine DePasquale
Pretty awful experience, because the food and wine are not that great but the bad 'service' (there really isn't any to speak of) puts the experience over the edge from 'mediocre' to 'I'll never return'.Nothing earth-shattering to say here that you haven't read from others, but just to add to the chorus: the vibe is oddly attitude-y (from the staff!)--even when they're not busy (we were first in line when they opened at 5pm), and you get the sense that they don't want to deal with you, ask questions or be helpful in any way. That would be slightly less annoying if the food and wine choices were stellar or amazing in any way, but they're not. Staff skews young and not knowledgeable about the food or wine on deck. We tried two different wines and 3-5 appetizers....all pretty basic, I'll term it as 'elevated fast food'.For those to whom comfort is important: the chairs are hella uncomfortable; at 5pm, the sun (depending upon time of year) is blasting in your face; the staff won't bring anything so you're jumping up and down from your 1st grade-sized chair to get everything you need that didn't come with the food, and they don't have the tables organized in a way that maximizes customer comfort.After our apps and wine, we were so hungry, we went down the street to Giulia's for a real dinner.Overall, to help you avoid our mistakes, here's my best advice: skip Dear Annie and just go to Giulia's, sit at the bar, and have some truly good wine and freshly-made food from people who know how to run a restaurant.
Atmosphere: 2
Food: 1
Service: 1
Jon Li
Can’t wait to return!
Atmosphere: 5
Food: 4
Service: 5
Carolyn Peterson
One of our favorite spots for a cozy, intimate evening. The employees are extremely knowledgeable and intentional, providing excellent wine recommendations and adding to the warm welcoming vibe. I love that you can try different wines to find something you love. The food is also well balanced. A lot of people seem to down-rate Dear Annie for the prices, but you don't have to order a full meal here--plenty of folks come for just a drink.
Atmosphere: 5
Food: 5
Service: 5
Melinda Kothbauer-Kale
Excellent food. The rotating menu has great options. Our gluten free friend had plenty of choices, even desserts! Food and service were very nice. Great wine selection. A bit pricey, but a great special treat.Dietary restrictions: Gluten free crackers to replace bread. Gluten free cookies for dessert (amaretti).
Atmosphere: 5
Food: 5
Service: 5
Tamaryn Watzman
Stopped by for a glass of wine with friends (didn’t try any of the food, so can’t comment on that aspect). Wonderful atmosphere, BUT as many reviews have noted, 20% automatic gratuity for half-service is… a lot. I’ve worked in food service for almost 7 years, and always tip; 20% is my standard for full meal dine-in. However, $40 for 2 glasses of wine (and you go up to the counter to order)… I would have definitely tipped at least 10%, but would have appreciated the option to *not* pay $20 for a single glass of wine. ?That being said, I *would* like to return for an actual full meal dine-in experience — at which point 20% gratuity would feel appropriate. ☺️
Atmosphere: 5
Service: 4
Alexa Back
Love the vibe. Good wine and food. Gets crowded so be
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Cheese Plate
Cassie Meyer
Dear Annie has the best vibes with an incredible selection of wines. The staff is incredibly helpful and always help you find a wine you'll enjoy. The inside is super cozy and their outdoor space is great during the summer months.
A truly special place. Some friends and I ate literally each item on the menu and there was no disappointment among us. We ordered the whole menu to share and we’re each thrilled— incredibly rare!! Here were my highlights: The sea dog swapped out my reality for a new, more glorious one! The Fumet flooded my eyes with briny, joyful tears and goosebumped my skin. The smoked blue monkfish was utter perfection, at least to the taste buds of this southern Appalachian who grew up on great smoked meat sandwiches. The wine options are unparalleled, delightful, and surprising! The ordering at the counter is great— easy to pop over if anything is needed and gives opportunity to look at the curious and homey decor. This might be an ideal neighborhood restaurant!! Can’t wait to return soon and often!
Atmosphere: 5
Food: 5
Service: 5
Valentin Frank
The food is perfect, but the atmosphere and service are so much more than just perfect. One of the loveliest places I've ever been, the wine selection is to die for, and I've never eaten the same meal twice.Vegetarian options: Plenty of pescatarian and vegetarian options. There are vegan options, but not a huge variety.Parking: Very little parking possible. Try using the bus or the T
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Olive Oil-Poached Cod
Oindrilla Chatterjee
This place boasts a fantastic wine selection, a cozy, charming interior, and friendly staff. The staff is exceptionally helpful, guiding you to choose the perfect wine option to suit your taste. They also regularly host special events and pop-up stores. Keep in mind, it can get quite busy and crowded on weekends, so finding a spot might be a bit of a challenge. The last time I visited was for a cheese event in collaboration with Formaggio Kitchen, and the special menu featured an array of delicious cheese options that truly impressed.
Recommended dishes: Cheese Plate
Beckie Darlington
We are visiting Massachusetts from London and a friend recommended Dear Annie - we couldn’t have been more pleased. The natural wine selection was incredible, we tried a few really interesting and lovely glasses. And the food was delicious, we really loved every dish. Plus super stylish and comfortable interior. Hope we have a chance to come back one day.
Atmosphere: 5
Food: 5
Service: 5
Barbara Booras
If only we had more places like Dear Annie in Boston! Dear Annie is a rare gem for this city that offers up the charm of a Brooklyn or San Francisco wine bar. It’s cozy and inviting atmosphere make dining at Dear Annie like you’re visiting with friends. They’ve got a beautiful selection of Natural Wines and easy going snacks. The well-versed team is always happy to taste you on some pours to make sure you find the perfect glass. Cozy up at their communal table or grab a spot in the sunshine in warmer months. Careful - it’s the kind of place where hours easily slip away as you sip on a beautiful glass. Don’t forget the bottle shop and take home a new favorite before you leave!
Dear Annie is a cute wine bar where you can try a variety of different wines. If you are going to have more than 1 glass of wine it is definitely worth it to get a bottle price wise than get a couple single glasses. It can get pretty busy since it is a small establishment. They let us stand and enjoy a glass of wine while waiting for a seat to open up which I thought was very nice. The staff is very friendly and knowledgeable of wine, I enjoyed the wine that was recommended to me. There us no table service - you go to the counter to order which I don’t mind. There is an automatic fee applied to your bill that serves as the tip.
Atmosphere: 4
Service: 4
Automatically taking 23% tip when they are not even serving wines, waters nor a single napkins or utensils? Ridiculous. They're literally taking orders from counter and don't even bring checks to the table. Which SERVICE are we paying for?
Best atmosphere in Porter Sq…go during golden hour.
Atmosphere: 5
Pretty awful experience, because the food and wine are not that great but the bad 'service' (there really isn't any to speak of) puts the experience over the edge from 'mediocre' to 'I'll never return'.Nothing earth-shattering to say here that you haven't read from others, but just to add to the chorus: the vibe is oddly attitude-y (from the staff!)--even when they're not busy (we were first in line when they opened at 5pm), and you get the sense that they don't want to deal with you, ask questions or be helpful in any way. That would be slightly less annoying if the food and wine choices were stellar or amazing in any way, but they're not. Staff skews young and not knowledgeable about the food or wine on deck. We tried two different wines and 3-5 appetizers....all pretty basic, I'll term it as 'elevated fast food'.For those to whom comfort is important: the chairs are hella uncomfortable; at 5pm, the sun (depending upon time of year) is blasting in your face; the staff won't bring anything so you're jumping up and down from your 1st grade-sized chair to get everything you need that didn't come with the food, and they don't have the tables organized in a way that maximizes customer comfort.After our apps and wine, we were so hungry, we went down the street to Giulia's for a real dinner.Overall, to help you avoid our mistakes, here's my best advice: skip Dear Annie and just go to Giulia's, sit at the bar, and have some truly good wine and freshly-made food from people who know how to run a restaurant.
Atmosphere: 2
Food: 1
Service: 1
Can’t wait to return!
Atmosphere: 5
Food: 4
Service: 5
One of our favorite spots for a cozy, intimate evening. The employees are extremely knowledgeable and intentional, providing excellent wine recommendations and adding to the warm welcoming vibe. I love that you can try different wines to find something you love. The food is also well balanced. A lot of people seem to down-rate Dear Annie for the prices, but you don't have to order a full meal here--plenty of folks come for just a drink.
Atmosphere: 5
Food: 5
Service: 5
Excellent food. The rotating menu has great options. Our gluten free friend had plenty of choices, even desserts! Food and service were very nice. Great wine selection. A bit pricey, but a great special treat.Dietary restrictions: Gluten free crackers to replace bread. Gluten free cookies for dessert (amaretti).
Atmosphere: 5
Food: 5
Service: 5
Stopped by for a glass of wine with friends (didn’t try any of the food, so can’t comment on that aspect). Wonderful atmosphere, BUT as many reviews have noted, 20% automatic gratuity for half-service is… a lot. I’ve worked in food service for almost 7 years, and always tip; 20% is my standard for full meal dine-in. However, $40 for 2 glasses of wine (and you go up to the counter to order)… I would have definitely tipped at least 10%, but would have appreciated the option to *not* pay $20 for a single glass of wine. ?That being said, I *would* like to return for an actual full meal dine-in experience — at which point 20% gratuity would feel appropriate. ☺️
Atmosphere: 5
Service: 4
Love the vibe. Good wine and food. Gets crowded so be
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Cheese Plate
Dear Annie has the best vibes with an incredible selection of wines. The staff is incredibly helpful and always help you find a wine you'll enjoy. The inside is super cozy and their outdoor space is great during the summer months.
Atmosphere: 5
Service: 5
Restaurantji Recommends
A truly special place. Some friends and I ate literally each item on the menu and there was no disappointment among us. We ordered the whole menu to share and we’re each thrilled— incredibly rare!! Here were my highlights: The sea dog swapped out my reality for a new, more glorious one! The Fumet flooded my eyes with briny, joyful tears and goosebumped my skin. The smoked blue monkfish was utter perfection, at least to the taste buds of this southern Appalachian who grew up on great smoked meat sandwiches. The wine options are unparalleled, delightful, and surprising! The ordering at the counter is great— easy to pop over if anything is needed and gives opportunity to look at the curious and homey decor. This might be an ideal neighborhood restaurant!! Can’t wait to return soon and often!
Atmosphere: 5
Food: 5
Service: 5
The food is perfect, but the atmosphere and service are so much more than just perfect. One of the loveliest places I've ever been, the wine selection is to die for, and I've never eaten the same meal twice.Vegetarian options: Plenty of pescatarian and vegetarian options. There are vegan options, but not a huge variety.Parking: Very little parking possible. Try using the bus or the T
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Olive Oil-Poached Cod
This place boasts a fantastic wine selection, a cozy, charming interior, and friendly staff. The staff is exceptionally helpful, guiding you to choose the perfect wine option to suit your taste. They also regularly host special events and pop-up stores. Keep in mind, it can get quite busy and crowded on weekends, so finding a spot might be a bit of a challenge. The last time I visited was for a cheese event in collaboration with Formaggio Kitchen, and the special menu featured an array of delicious cheese options that truly impressed.
Recommended dishes: Cheese Plate
We are visiting Massachusetts from London and a friend recommended Dear Annie - we couldn’t have been more pleased. The natural wine selection was incredible, we tried a few really interesting and lovely glasses. And the food was delicious, we really loved every dish. Plus super stylish and comfortable interior. Hope we have a chance to come back one day.
Atmosphere: 5
Food: 5
Service: 5
If only we had more places like Dear Annie in Boston! Dear Annie is a rare gem for this city that offers up the charm of a Brooklyn or San Francisco wine bar. It’s cozy and inviting atmosphere make dining at Dear Annie like you’re visiting with friends. They’ve got a beautiful selection of Natural Wines and easy going snacks. The well-versed team is always happy to taste you on some pours to make sure you find the perfect glass. Cozy up at their communal table or grab a spot in the sunshine in warmer months. Careful - it’s the kind of place where hours easily slip away as you sip on a beautiful glass. Don’t forget the bottle shop and take home a new favorite before you leave!
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Cheese Plate