Il Massimo

I recently visited Massimo for dinner with friends and it was simply superb. The ambience is warm and inviting, with soft lighting and elegant décor that makes the whole place feel upscale yet comfortable. We were greeted right away and seated in a cozy spot. Our waiter, Ledjon, was outstanding — attentive without being overbearing, very knowledgeable about the menu, and genuinely enthusiastic about the food and wine pairings. We started with the Burrata — rich, creamy mozzarella with prosciutto di Parma and roasted peppers — absolutely delicious and beautifully presented. For mains, I had the Spagheti alla Carbonara, which tasted like true Italian comfort food, while my friend tried the Branzino, a Mediterranean sea bass with lemon, fried capers, and Calabrian chili — cooked perfectly and bursting with flavor. For dessert, the Tiramisu was the perfect ending — light, creamy, and just sweet enough. Every course came out at the right pace, and Ledjon made sure our glasses were never empty. The prices are fair for the quality, and the overall experience felt polished yet welcoming. I’ll definitely be back — and I’ll be asking for Ledjon again.

We had an amazing dinner at Il Massimo! I ordered the Filetto di Manzo, and it was out of this world good — cooked perfectly and full of flavor. For dessert, I had an Affogato, and it was the perfect sweet ending — so rich and delicious. My wife had the Short Rib Gnocchi, which she really enjoyed. We shared a great bottle of Cabernet, which paired beautifully with everything. Our server, Sal, really stood out — attentive, personable, and clearly passionate about what he does. He made great recommendations and made us feel genuinely welcomed throughout the evening. The ambiance was incredible — elegant yet comfortable — and the wine selection was top-notch. Can’t wait to come back!

Absolutely phenomenal! I had dinner II Massimo last night, and Ledjon was our waiter and it was hands down one of the best dining experiences I’ve had in a long time. From the moment we walked in, the atmosphere was warm and inviting the lighting, music, and decor all made it feel authentically Italian. Our server Ledjon was friendly, attentive, and made great recommendations. I ordered the fettuccine alfredo with grilled chicken, and it was perfectly creamy and flavorful without being too heavy. My friend got the spaghetti carbonara, and we both agreed it tasted like something straight out of Rome. The garlic bread was fresh and buttery, the portions were generous, and the tiramisu for dessert was the perfect sweet ending. You can tell everything is made with care and high-quality ingredients. Highly recommend this place for date nights, family dinners, or any time you’re craving real Italian food. I’ll definitely be coming back!

We stopped by II Massimo for dinner with my family. The food took a bit longer to arrive than expected, and the server seemed preoccupied with other tables. At one point, I tried to get their attention, but they were deep in conversation with the neighboring table. It made us feel a little overlooked. That said, the food was decent—good, but not particularly memorable. We ate, enjoyed what we could, and headed out.

Came here to celebrate my wedding anniversary and the service was friendly and prompt. The food was also delicious! I ordered the Carbonara and was pleased to see the raw egg yolk (not a lot of places do this anymore)! The salad was well dressed and we had to end with my favorite dessert, Tiramisu. Yum!

This restaurant was a great time! I went there with a couple of friends for a celebration and we all loved the experience. Our server Emma was so attentive to us and really made the dining experience more enjoyable. Would definitely go back just to have her service again. The mussels and eggplant appetizer were by far the best thing we ate. I definitely plan on going back soon and have already told everyone I know about this restaurant! 10/10

From the moment you step inside,you can feel the relaxing atmosphere. The hostess was polite and courteous. Our server was attentive and answered all our questions about what was on the menu. The food tasted good, nicely proportioned. It was a good restaurant. Outdoor seating is also available. I definitely recommend it.

We came to Boston to celebrate a birthday and chose to eat here for dinner! We were very impressed with the food, atmosphere and especially our servers Semo and Marissa! Highly recommend!

Yesterday I came here with some coworkers, i ordered the short rib gnocchi and cannoli trio and tried some calamari appetizer. Calamari appetizer-Good lemony flavor, tasted fresh. Gnocchi with short rib ragu- short rib was super tender and juicy, sauce was sweet but not too sweet. Good flavor. The gnocchi had just the right amount of chew and was generous with the portion. Cannoli trio-1 chocolate chip cannoli, 1 orange cannoli, 1 pistachio cannoli. The cannoli cream tasted very fresh, just the right amount of sweetness, very generous with the chocolate chips. Super tasty. Overall: if ever in the area, check them out, they are quite good.

I decided to try this restaurant for the first time with my best friend recently. Right off the bat I had made a reservation and I had called to notify them that we were going to be less than five minutes late due to looking for parking in Legacy please, be individual I spoke to was very dismissive on the phone immediately when on to say that they had a 15 minute policy of holding the table and After that they had to give the table away and really just didn't let me finish talking and was very expensive which I did not appreciate. We ended up walking in within the next three minutes so we were nowhere near that 15 minute policy. Fast-forward to our food and service inside the restaurant. We had two different servers and they were both nice and attentive. I had ordered the meatball and pasta dish and my best friend had ordered gnocchi. Both dishes were very tasty! The decoration and set up of the restaurant was very nice and elegant.

I was lured to this place because of their patio. Sitting on the patio, I was enjoyed a glass of Sauvignon blanc while reading my book. This restaurant offers complementary bread and olive oil. The olive oil has real olives in it which is a nice touch. My entree was the fusilli con polpette e burrata. While the presentation was beautiful, the entree itself wasn't flavorful. I asked my waiter for some red pepper flakes to add some flavor. Maybe I ordered the wrong thing, but I won't be rushing back anytime soon.

Tried for first time based on reviews and it met up to expectations. Had interior look of an established restaurant but first floor wasn't as warm feeling as I would preferred - seemed more efficient to clean and move tables to fit parties than comfortable. Had a delicious dinner at Il Massimo. Veal was tender and had a scrumptious demiglaze. The prosciutto wrapping was appropriately cooked also - so often, at other places, it is undercooked or burnt. Waitstaff were attentive and teamed up well. We have avoided Federal Hill in past but complementary valet parking convinced us to go this time.

I really wanted to like Il Massimo given the convenient location (for anyone visiting Legacy Place in Dedham). Unfortunately, we were underwhelmed in every respect The service was 'okay' - not particularly bad, but not great either. We were surprised to see the folks delivering food from the kitchen went to wrong person/table on the first attempt nearly every time we witnessed them. The food was 'okay' - not particularly bad, but not very good either. Our dishes were VERY over-sauced and when my fiancée complained that her broccoli rabe tasted "off" she was told "broccoli rabe often tastes sour." Really? You don't asssume the 50-something-year-old couple you're serving has never had broccoli rabe before? She eats all the time and usually loves it. It was inedible. The ambiance is in the same category, not 'bad' but not very inspired either. I'm sort of shocked the Yelp community finds Il Massimo with 4-star-worthy. I hate to say, but I think they can do much, much better -- and I hope they do.

I recently dined at il Massimo while on a business trip and had a mixed experience. The service was friendly and attentive, and the restaurant had a lovely atmosphere--warm, inviting, and perfect for a nice night out. Unfortunately, the food did not live up to the ambiance. The chicken was dry and overcooked, lacking the tenderness you'd expect from a dish at this level. The ravioli, which I was excited to try, was overwhelmingly sweet--almost like a dessert, which didn't pair well with the accompanying duck. It was an odd combination that missed the mark for me. While the service and setting were enjoyable, the food left something to be desired. Hopefully, with some adjustments to the menu, the dining experience can match the otherwise pleasant environment.

Food was good. Service was good as well. Ambiance was nice. There were booths that we sat in but there were plenty of high tops and dining area.

Dropping the 5 star because this place actually has a Happy Hour for food.....and a pretty good one. Sit at the bar and order early and all appetizers are 1/2 off.....yay!!!!!! Not only that but great selection and very yummy. While I only really dine at the bar and have eaten here a bunch of times, each time I was able to fully enjoy the food and the good selection of wine available. While the food isn't up to the caliber of nearby Capitol Grill.....it's good and a lot more affordable. Great place to eat after shopping or to stop for quick drink and appetizer.

Came here for a friends bday and was the perfect environment. They were very nice and provided a free dessert. We wished the appetizer came with either bread or cracker so it would be easier to eat but the burrata tasted great. The pasta was delicious and the sauce vas very rich. The tiramisu was light and fluffy. Overall had a great experience

I really enjoyed this place. Went for lunch to celebrate my friends birthday and it was fantastic. The food was delicious, the service was very fast and attentive. The ambiance was very nice, loved how bright it was in the restaurant. Would go back and definitely recommend to others looking for some good food.

I enjoyed my restaurant week visit to this restaurant. I was surprised the 3 courses were actually not that bad and had quite the options. We got calamari, gnocchi with chicken, and tiramisu for dessert. The choices we picked were nothing special, BUT the calamari and tiramisu were delicious! The tiramisu especially was big for its size. We also had excellent service. We requested to sit outsize which they kindly accommodated for us. It was a very nice day out with a slight breeze. It was a perfect day.

Came to Il massimo legacy place for my mother birthday lunch. This restaurant has one of my favorite ambiance. The light is kind of dim, which I honestly really like. The service was good really nothing to complain about. My sever was very kind and fast and served us with a smile on his face. We ordered fried calamari as an appetizer, it was delicious and they tasted very fresh also. As an entree we order risotto and seafood pasta. The pasta was not that good as my mother said she could taste the same of the clams in it. My risotto tasted pretty good but it did bot taste like an Italian traditional risotto. Overall I gave this place a 3.5, you should definitely check it out.

We ate there Saturday night 1/25 and sat at the bar. It was before 6 so there were plenty of seats available. We started off with the calamari which was excellent! Tender as i've ever had it. For the entrees i got the nicely portioned lasagna and my wife got the scallops with risotto. Both meals were really tasty and then for dessert i got chocolate lava cake with ice cream and it was excellent. Everything was what you'd hope for at a fairly expensive restaurant. The reason i'm giving four instead of five stars is the bartender. Not terrible, but he didn't smile or give off a very friendly vibe.

Right when we walked in, I noticed the ambiance was pleasant and soothing. Service was great. Our waitress was very friendly and checked on us multiple times. Unfortunately the food did not live up to its ambiance and service.. I had the squid ink pasta and I was pretty disappointed. The seafood tasted over cooked

Had dinner with a friend recently and was interrupted by the fire alarm blaring . Everyone was asked to go outside and wait in 30 degree weather with a wind chill of 23 degrees. Neither one of us had finished our dinner, but were not offered any type of discount for our inconvenience. The manager only offered a free dessert for one person. The manager obviously did not care about customer service. We have been to this restaurant multiple times, but this will be our last visit.

It was our first visit to the restaurant for dinner: it has been on our list for quite some time. (I am posting this about two months later!) A valet whisked our car away, to return it on our departure- quite convenient. We were seated in a comfortable spot in the old fashioned dining area- a pleasant space. Our server Nathan was personable and efficient. We had decided to observe "dry January " - and now being out of it we ordered some wine: a glass of Montepulciano and a Nero d Avola, and a large bottle of sparkling water. For food we had a Saltimbocca and a pasta special. Both were good but not extraordinary. We shared a Ricotta Cheesecake and I ended with an espresso. The check came to $150 without the tip. All in all a pleasant experience. We will be back.

What a wonderful experience! We decided to have a random Thursday night dinner with friends. The atmosphere is chic elegance. The service was impeccable. We started with the calamari appetizer which was phenomenal. The blood orange martini was heavenly. Our beverage glasses were never empty, including water. The menu was so perfect. We could not decide... I ended up ordering the Facilli and meatball Barata. For dessert we had the three cannoli and the cheesecake. I have to say it, this is better than anything I've had in the North End. The prices were much better as well (I'm sure you can believe that). I grew up on Italian food and the San Marzano marinara was to die for. Everything was perfect. We will certainly return!

Ambiance and the drinks are the biggest reasons to come here. Had the appetizer eggplant parm. Just way too much grease to be enjoyable. Had the lunch pizza, and the dough was strange. It didn't seem like it was a classic yeasted dough, and while it had grill marks, it didn't taste grilled. Bummer.

Food here is not good at all, prices are a joke for the quality. We barely put a dent in our plates, server didn't seem to care - didn't ask what's wrong or offer to take it off the bill. Service wasn't great. Cute interior but experience doesn't live up to it. Not worth the price at all you'd be better off at Cheesecake Factory.

We came by for our 530pm reservation. The place is in a large very busy shopping center type area. There is a parking facility attached but we chose to take our chances parking in the open lot closer to the restaurant. We got lucky and nabbed a spot. It was extremely busy and crowded on a Saturday night. We were seated promptly and the table was set for a birthday - mine. Our daughter and son in law are hosting and our new grandson is with us. He slept through the whole meal. Our server came by and explained the specials and various dishes. The table was decked out with stars and a nice acknowledgement of my birthday. We got cocktails and they were perfect and as ordered. I got the octopus appetizer which was wonderful and served in a bowl almost like a gumbo. The octopus was delicious and well flavored. I thought that it could have easily been served as a main. For my main I got the Mediterranean sea bass, aka Bronzino. It was nicely butterflied and served with tail no head. It was excellent and well flavored. Others enjoyed their food. Service was great. The sommelier came by to decant our Brunello and the wine was very nice. Our server was attentive and friendly. The bus service could be improved. My main was brought before our cocktail and appetizer dishes were cleared. They messed up the orders regarding who ordered what. Minor negatives. Dessert was two nice coup glasses filled with lemon sorbet with a cookie and a candle. Very nice. Ambiance was an Italian bistro. Place had a bar on the right as you enter and booths of all sizes and various tables we sat at a round table in the center of the main dining area. No comment on value as we were treated by our daughter and son in law. We would return. Mark & Nancy.

The first impression was damaging, but the food was better than average. (on the first impression, three employees examined the seating chart together and spent about 4 minutes determining if they could somehow, some way fit us in. Then they led us upstairs and we all looked at each other like, what is this, a scam? But the red was quality and the service was engaging. It was surprisingly easy to carry on a conversation as the room ultimately filled up, so we'd go back again.

I've always had great experiences here! The food is delicious and portions are big plus they have great drinks. The octopus and meatballs are my favorite apps and we had the eggplant rollatini last time which was a special and was amazing! You can't go wrong with the fusilli with meatballs and burrata, pork chop, carbonara and gnocchi. Great place for a nice dinner or sitting at the bar for some apps.

Good Food Nice ambiance inside. Noise level is moderate but not too loud to prevent conversation. Nice large bar area. Food was excellent with nice menu choices and some good specials. We had the cod special which was a nice sized portion. Service was fair, at times slow but attentive. The bread and olive were nice and service was great! Ordered a squid ink fettuccine with lobster which was delicious and portion was right. Lasagne was great too. Overall a nice restaurant with quality food and drinks. It is a bit pricey. Keep that in mind. Thanks

Ambience was good. Food wasn't anything special. Standard Italian fare. Server was nice. Was a one and done for me

Ambience is always superb, and is a great place for a casual evening out or a fancier celebratory dinner! Last night I visited once again to have desserts and drinks, and the olive oil cake is to die for. A MUST if you have room after dinner!

Food & drinks are good, service was good and the ambiance is nice. Highly recommend!

My partner and I got the pizzetta fico & gorgonzola, orecchiette con cime di rapa, and fusilli con polpette e burrata, plus the Bee's Knees cocktail - TASTE: 5/5 - we really weren't expecting the food to be this good lol, and were pleasantly surprised! The pizza was definitely our favorite w the sweet figs, balsamic glaze, arugula, gorgonzola cheese, and fatty prosciutto. My orecchiette was just what I was craving w its broccoli rabe pesto and sausage, and the fusilli had a nice, sweet tomato sauce. Even the complimentary bread was flavorful and super cheesy, and our drink was perfectly balanced too TEXTURE: 4/5 - the focaccia bread was spongey and on point for dunking into olive oil. Both pastas were al dente PRICE: 4/5 - total came out to $110 SERVING SIZE: 4/5 - we were so stuffed; took half the pizza and most of my pesto pasta home SERVICE: 4/5 - walked in at 5pm on a Sunday, and there was plenty of room inside. We were seated quickly, and our waitress was nice. There was a bit of a stretch after getting our pizza and waiting for the pastas next ATMOSPHERE: 4/5 - a traditional, elegant interior w dark and moody lighting PARKING: 5/5 - plenty of parking in Legacy Place plaza

It has been a number of years since Il Massimo of Dedham has opened and with Covid, dining there just didn't happen until this week. This restaurant has maintained their warm ambiance in decor as well as in management and waitstaff. Having dinner there is such a joy. Manager Simo and our waiter Peter as well as other waitstaff and assistants are so hospitable. Beginning with the fabulous pizza, Pizzetta Fico & Gorgonzola, we were more than delighted with the flavors of black Mission figs, Gorgonzola cheese, the delicate Prosciutto di Parma, caramelized onions, and Arugula on a perfect crust. That was followed by our selection of the Insalata di Spinach salad - and the foccaccia bread with olive oil Gnocc was perfection as always. No doubt, we were very relaxed and so well fed. The timing of the main course was definitely on the mark thanks to Peter, and we were ready to indulge. Our guest was very pleased with the Gnocchi al Forno, house-made potato dumplings, four cheeses, San Marzano Tomato pink Sauce, all baked in Clay. Hubby tried and was pleased with the Spaghettoni alla Carbonara made with Guanciale, raw farm eggs, and seasoned with Pecorino Romano, and crushed black pepper. I was in heaven with my choice: Short Rib Gnocchi. That slow braised pulled Short Rib Ragu, with Parmigiano Reggiano and Gremolata seasoning was what I love and I had not enjoyed that in a long time. It was a wonderful dining experience thanks to everyone there!

Great Italian food and great service. Parking was really close. Nice wait staff and fair prices for good food portions Seymour the manager was really great!

I go here for lunch pretty often. Lots of their dishes are good including the octopus, beef carpaccio, risotto, and tiramisu. I also like their cocktails. They used to serve a good gin spritz and now they have a sparkling sangria. The only downside is that the service can be spotty. This could be because I am often there about 3:00 pm. Orlando is a good waiter when we get him.

I came for lunch and did the lunch special. The complimentary bread and olive oil, Caesar salad, and cannoli were delicious. The main dish I ordered was the gnocchi in red sauce and it was so so. Overall I'd go back again!

Service was great, but the food was subpar. It felt like all the money was spent on the decor, at the expense of the food quality. We spent too much Ang got not much in return

Had a chance to try this restaurant for lunch the other day. I didn't order from their lunch menu, rather their dinner menu. I ordered a cocktail and a pasta dish. The fish I ordered was squid ink pasta with lobster meat. I asked the waiter if I can have extra cooked pasta since I don't like mine Al Dente. He said pasta is pre-cooked so he basically said no extra cook time, then he proceed to ask me if I want to add chicken or beef? I was very confused since I ordered a lobster pasta dish, didn't think I'd need to add more protein to my dish. The pasta came out quickly and as suspected the pasta was al dente. The sauce and lobster meat saved the dish. The sauce was very tasty. My pineapple cocktail was very strong, caught me by surprise. The place is quite big and clean. I sat a wobbly table but I didn't say anything because I just wanted to have a quick bite and leave.

Stopped in for a quiet elegant lunch at legacy place. This was a first time visit but not the last. Our waiter recommended the porcheta panini but trying to be healthy we opted to split the panini and a rucola salad (arugula). Both were very satisfying and I really liked how simple yet flavorful the salad was. Would order that again and again. All my efforts at making healthy choices were thwarted when my husband insisted we split dessert. Each item on the dessert menu looked better than the last. We settled on the molten lava cake which was warm rich dark chocolate decadence with an accompaniment of vanilla gelato. Holy cow! So good. Really enjoyed this place, the food and the service. The only thing I would recommend they do differently is to skip breading the fries. I really don't understand this trend. And to be fair, of the breaded fries I've had, these were the best but I am a purist and think that potatoes can stand on their own. My husband said they were great.

Went there for the first time today with 10 woman. We made reservations in advance for restaurant week (3 courses for $24) I asked when making the reservation if we could get separate checks and they were happy to oblige providing we told the server before ordering Our server was very accommodating, food was outstanding and proportions were plentiful. A very good selection considering it's a special. All of us were very pleased and will definitely be back

The few times we visit Il Massimo has always been lovely -- we appreciate the staff there and the food is pretty consistent. For instance, we ordered one salad to share and we didn't ask for extra plates or for it to be split but it was thoughtful of them to split it for us into two smaller bowls so we didn't have to split it amongst ourselves. The pastas are also very enjoyable and flavorful. The service has always been kind and they always share great recs. They can be on the busier side even during the weekdays, and the bill can easily add up (a bit on the pricier side, but it's a nice treat). Def will be visiting again.

Food 10/10, ESPRESSO MARTINI FLIGHT 100000/10. The service was great and the waitress brought us bread 3 times. The atmosphere is also 10/10. Looking forward to going back to sit at the bar.

Very solid dinner experience. We enjoyed the food (insalate mista, salmon, pasta with broccoli rabe pesto, fettuccine ragu, gelato), and wine selection. The service was wonderful: extremely friendly and attentive. The atmosphere is classy and pleasant, so we took our time chatting and had a long leisurely meal. Would definitely visit again.

Pleasant place, convenient parking. The food is of reasonable quality (we ate calamari, seafood risotto, salmon, ravioli and tiramisu). There are no sparks and no falls. Good service.

We went to Il Massimo in Dedham for lunch. There were 14 of us. The waitstaff was efficient, friendly, and professional. Everyone's food (appetizers, entrees, sides, and dessert) were fantastic. I would highly recommend this restaurant.

Food is fantastic!!! CJ the bartender was a true professional and very adept at handling a busy bar. Prices are about right for a place of that quality, ambience and decor were on point. I would return if I lived in that area.

Loved it here! Great service and super accommodating for allergies. Everyone in our party could find many delicious options even with their dietary restrictions. We had to change the time of our reservation the day of and the staff was very helpful. They even put a birthday sign on the table for our celebration. It is a nice place that also feels accessible and not stuffy.

Yummy food! Consistently good service!!! Beautiful location and ambiance. Love this place!

Ordered 2 large pizzas (1 cheese ,1 sausage) When I got the pizzas they where medium in size,did not look completely round like normal pizzas,gummy crust,salty as heck and the "sausage"pizza was SALAMI! Not only was it wrong but the salami the type of salami you buy to have with crackers and cheese with wine(the cured stick type)! Never again.

We went here on a whim for dinner and was not disappointed! We shared the Carciofi (Baby Artichokes, Crushed Pistachio, Golden Raisins, Calabrian Chili Aioli) for our starter. It was yummy and interesting and reminded me of dishes I've had in Europe. For entrees I had Spaghetti al Nero con Aragosta (Black Squid Ink Spaghetti, R.I. Lobster, English Peas, Seasonal Mushrooms, Lobster Cream, Toasted Bread Crumbs) and my husband had Short Rib Gnocchi. Both were very good and very rich. The portion sizes were quite large and we were able to take home and make another meal from our leftovers. I also had an espresso martini which was excellent and our waitress was very sweet and attentive. I'd say the only negatives were it's a bit pricey and we were seated alone in a random back room rather in the main restaurant area which was strange because there were plenty of tables available.

The scampi and calamari was delicious. Our server was very friendly and attentive. Loved the decor and lighting.

An elegant ambiance with great service and very good food. I'm very picky about Italian, having grown up with it. We went for lunch and ordered the 24$ special. Wonderful appetizer Ribollita Toscana was so good! The Gnocchi was also very good. The pistachio cannoli was amazing. Good wine, great atmosphere, great service. We will definitely be back! Parking can be a challenge.

This is one of my two favorite restaurants in Boston. I've been here several times, twice with a large group. Sal, the server I request, is the best. He handled our groups with ease, and he's charming (when was the last time you greeted your waiter with a hug?). They have a weekday three-course lunch special that is too hard to choose from. I highly recommend the eggplant parm and any of the appetizer salads. Their pistachio cannoli is really tasty too!

First we love the staff at the restaurant...they are kind and considerate...just great! The food here is the problem and wildly inconsistent. We had my wifes' birthday dinner here and the food was way off...the manager who promised to take of us was no where to be found! Tonight celebrating our 38th anniversary my veal was way overcooked and not of good quality...it was more texture than taste. Should we have complained...absolutely yes but these were celebratory meals and we just left! Unfortunately you take your chances when dining here...your meal can be very good or simply very pedestrian and certainly not worth the price (they just raised their prices).