Contessa Boston — Restaurant in Boston

Contessa opened to the public on June 22, 2021 on top of the recently renovated Newbury Hotel. I visited two times three and four weeks after their official public opening. These are my thoughts.

There are no phone reservations and no walk-ins. The only way to make reservations is to book online through Resy, or to email the restaurant directly. This is what was recommended to me by the staff, as Resy is not allocated very many reservations. I’ve since been told that the reservations allotted to the general public are limited in order to create hype and demand. Quite a deceitful business practice! In all honesty, Patrick Bateman would have had an easier time making reservations at Dorsia.

Contessa is only open from 5pm-10pm on Sunday, Wednesday, and Thursday, and 5pm-11pm on Friday and Saturday.

The entrance to Contessa is on Newbury Street. There is a long dark hallway with an elevator at the end. Neither the front of the elevator nor the buttons inside indicate which floor the restaurant is on. More descriptive signage is necessary, so that people know that they didn’t mistakenly step into the hotel's service elevator.

Upon entering the restaurant there’s a small podium where the host is standing. He’s a heavyset gentleman with circular glasses named Peter. I found him to be incredibly snobby and rude. Apparently, “the restaurant is completely booked for the next ninety days”, but on the two separate days that I visited the restaurant was nearly empty for the first few of hours of service and never reached more than 50% full when I left after 8pm.

There is a sit-in bar with only eleven seats near the entrance to the restaurant. It fills up within the first few minutes of opening. They have a small waitlist, but there is no designated waiting area, so you just give your name to a bartender and then stand behind the seats at the bar and wait to be called. You are free to order a drink and stand there while you are waiting. The bartenders were so-so. One male bartender, S, came across as very fake and curtly, a female bartender, K, was warm, attentive and welcoming.

Words cannot do justice as to how beautifully designed this restaurant really is in person! The floors are adorned with a stunning array of tiles in rose, white, teal, and grey. The tables all have wood grain or white tops and are surrounded by red leather or velvet seats in a bluish-green colour. The tableware is also green with gold accents, while I believe the stemware was made by Riedel.

However, the rooftop aspect of Contessa is completely spoiled by these large barriers with railings on top that completely block what would otherwise be an amazing view. When you are seated at a table, the only things that you can see are the tops of the buildings and the sky. I am not sure as to why these large dull-looking railings are there blocking the view, but they completely spoil it to the point that it’s reasonable to say that this is a rooftop bar in name only. The windows on the days that I went, which were both 75-80 degrees, were closed. What a shame!

We ordered wine and a few items off of the main menu which were good but nothing special. The wait staff for the most part was very polite, but there were more than a few waiters with scowls on their faces as if they really didn’t want to be there and it showed. The bill was in line with the cost of fine dining, but the service was seriously lacking.

Overall, I enjoyed my experience at Contessa, but I will not be going back again. The reservation process was unnecessarily complicated and deceitful, the food and wine was just okay, and the host was rude and snobby. Even though Contessa is technically a rooftop restaurant, you cannot enjoy the view due to large barriers that block it.

Ultimately, the goal of any fine-dining restaurant is to provide the customer with excellent service, delicious food, and to make them feel welcome, so that they will want to come back and dine there again. Unfortunately, in my case, Contessa did not accomplish this goal. Very...

I’ve been dining to celebrate my birthday at Contessa Boston for three consecutive years. Sadly, it’s gone from an elegant, upscale restaurant, with highly skilled, professionally trained and studied servers, to feeling like a very high priced pub hangout, that caters to spoiled young, and not so young, rich people who don’t know how to dress or act in a restaurant. Throw on an oversized sweater with a white tee shirt hanging down, put on your black, urban work boots, a hoodie, top it off with a baseball cap, sporting a sticker that says it’s “real”, smash that cap on your head, backwards so your hair pops out like you are at Fenway Park or the like, then go on up to the rooftop that is Contessa Boston. —Both women and men dress this way too, with only a few attired appropriately. -Contessa says they don’t accept athletic attire. Really? Patrons acted like they looked. A man at the bar, 30+, with two friends thought he was watching a game in a local during a special sports series, rubbing his stomach, raising his rumpled, untucked, flannel shirt, so he exposed bare skin. His jeans matched a beard growth that said something like, “Dude, it’s the weekend, I don’t I have to wash or shave.” –Far from a look of, “I did this to look urban sheik.” A group of four women, all late 20’s to 30’s sat at a window-facing table, and noisily swung the lamp, banging it down. It finally stopped working, rescued by a discouraged server, who struggled to make it function again. Then, a 40-something group, all dressed like they were going to go to Olive Garden, realized they were privileged and ended up in a setting were they could show they had money to spend, but no class. Their baseball caps and sneakers were well-loved, maybe once new and expensive? They also loudly complimented the waiter on his afro-textured hair style, asking him how he got it to look like that... He smiled and told them it grew that way and he trimmed it himself. The food was still amazing, with long wait times between courses, much over typical. When we asked where our second course was, our server reported… “It fell.” We asked what that meant and were told, “It just fell and had to be redone.” We were given a complimentary glass of wine while we waited for the new “not-fallen pasta dish” to arrive. Had we not asked, it didn’t appear that anyone was going to offer the wine, and apologize for the wait. Along those lines, it was challenging to get a basic water refill throughout the meal, mostly, we searched for a person willing to fill our glasses. Twice the sommelier responded, bringing ground pepper for our salad course, and refilling our water glasses. We felt bad because we had asked him to notify our server - but he took the lead. The main course arrived while I was in the restroom. With my linen napkin left in a crumpled mess beside it all, not the way I left it; everything looked like I had fled in a hurry just as it was served! A top-priced menu item plopped and lukewarm! The delays meant, it was late when we left. The pub atmosphere had turned to full college dorm attire for all ages. Needless to say, Contessa Boston needs to decide who they are, and who they want to be; and if the standards they suggest they have are real or imagined. Atmosphere and service are all a part of fine dining, and should be of the utmost importance when menu prices make for a bill of at least $500 for two. The restaurant management shows they don’t care because they did nothing. Plus, they turned tables all night, so we were the only ones who seemed to care about any of it. Sadly, I would say, if you are looking for an upscale, fine dining experience, where you’re spending a huge amount of money, one that falls outside a typical grab some grub after lying on the couch kind of day, don’t choose Contessa Boston. Maybe it was because Halloween was the night before all of this? Hey, at least the bill came right on time, and with the best service...

My wife and I had our 24th anniversary dinner at Contessa.

The ambience, atmosphere, and setting were absolutely stellar.

The service was excellent in almost every way. That said, at an upscale restaurant like this, charging the kind of prices they are charging, I believe the wait staff should be trained not to ask if they should remove plates. I worked at the Greenwich, CT branch of Paris-based Restaurant Guy Savoy as a waiter, years ago, and we were carefully trained to be able to tell when people were finished. Asking if they were finished and ready to have their plates removed was strictly forbidden. This is a small detail of elegance that a place like Contessa should observe.

Our cocktails were absolutely superb The appetizers were quite good, and kept us feeling like we were in for a good experience with our entrées.

The entrées, however, were extremely disappointing. The branzino was surprisingly small, and not appealing presented. The spicy lobster capellini was the biggest disappointment. There seemed to be no effort to present it beautifully, it was in a very small bowl kind of just thrown into it. The lobster pieces, though touted by our waiter as large, were quite minuscule and hard to find. The prices are far too inflated for what we received. All we can imagine is that we were paying for the setting and the ambience. Certainly not for the quantity or beautiful presentation of food offered.

Of the two desserts we ordered, the cake was dry, and virtually tasteless. We had to send it back. At a restaurant like this, nothing should ever need to be sent back -- it should be remarkable in every way. The other dessert (I forget what it was) was good. Not remarkable, but good.

When our waiter brought the Limoncello that I ordered after the meal, he accompanied it with "happy anniversary!" With such a gesture, there is an implication that it has been comped. I was very surprised that I was charged for it. When I asked later about this, I was told that the company's policy is not to comp anything for anniversaries or birthdays. This is extremely surprising at an elegant restaurant that charges the kind of prices Contessa charges. This was our 24th anniversary, and at all 23 of the others, there has always been some little thing comped to celebrate us. This no-comp policy seems small-minded and petty considering the prices they charge.

Overall, we feel that we could easily have had a more superior dining experience at any number of restaurants in the North End, for half as much as we spent at Contessa. This was extremely surprising considering how highly Contessa had been recommended. And I'm very disappointed to have to say it.

The final great disappointment that was the last straw for never wanting to set foot again in this restaurant -- and for making sure I spread the word whenever possible to avoid Contessa like the plague -- was that when I came back the next day and voiced my concerns to assistant manager Christopher Kundert, he didn't appear to take my concerns particularly seriously. There was almost a smugness in his demeanor as I listed my disappointments. Furthermore, I followed up by email and I never heard a word back. The least he should have done is to send a reply acknowledging my email. This lack of attentiveness to customer complaints sends a loud and clear message.

Please, find any other restaurant in Boston to eat. May I suggest Bertucci's? At least there you walk in knowing you'll get what...