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Massimo is classically designed to create a warm and lively setting. Massimo’s spacious dining room and glass-enclosed private dining room—including a full bar & lounge—make it the perfect place for occasions of all scopes and sizes, whether it’s a quiet night out with friends and family, or a boisterous celebration with dozens of guests.
Massimo has unique Italian wines from small boutique Italian winemakers (available nowhere else!) and a cellar selection from Italy, Spain and California. Our approach to wine is accessibility, quality and variety to encourage unfettered enjoyment.
3-Course PRESTO! Lunch
Multiple dates availableThree-Course PRESTO! Lunch Menu Available Weekdays 11:30-3:00 $16.95/guest
Multiple dates availableJoin us for Sunday Brunch! Available 10:30-2:00
Monday Prefix Dinner$29.00 per person
Multiple dates availableJoin us Monday nights for our special, 3-course, prefix menu for $29/guest including a glass of house wine!
$1 Oyster Monday
Multiple dates available$1 Oyster Special Every Monday!
Half Priced Apps
Multiple dates available
Mon - Thu 3:00 PM - 9:30 PMHalf Priced Apps Available 3:00-6:00 Weekdays!
A wonderful meal, great bottle of wine and incredible waitstaff made for a nice Tuesday night outing.
Went to Massimo for our 3rd anniversary. It was fabulous! Our waiter, Colin, was personable and knowledgeable. We had a quiet corner table upstairs and we were greeted with a Happy Anniversary card. The food was delish! A perfect night.
Great once again! Good food including Bolognese, Short Rib Gnocchi, Meatball appetizer. Great selection of Italian red wines as well!
Great spot for brunch. I would go back for sure!!!
Def will be going back again for brunch. The food was great, the bartenders were super friendly and drinks were on point!
Food was excellent. Great selection and prepared to perfection.
Food was good, but portion size just so-so. Duck confit was excellent. Ravioli dinner was adequate 5 ravioli. Scallop dinner included just 4 scallops, 3-4 Brussels sprouts and risotto. Scallops tasty, sprouts somewhat bland and risotto delicious.
We sat outside per our request so ambiance wasn’t fancy, but we enjoyed it. Service was fine.
I’m not sure we’d go back, but I would recommend giving them a chance.
First time there and was very impressed. Went to lunch with work friends and very good experience and excellent food! Will definitely be back!!
I came with a group of friends to celebrate my friend’s birthday. We loved the little touches of birthday decor on our table when we arrived. Overall, the food and drinks were very mediocre. Some of my friend’s dishes were extremely salty and my chicken parm was really rubbery and tough. The oysters also didn’t taste very fresh and had an off-putting taste. The only thing we collectively liked were the brussel sprouts and desserts. I don’t think we’ll be returning here for the food. There are many other smaller restaurants in the North End of Boston that are better in terms of food. The service was also very average. On the evening we went, it wasn’t even a packed restaurant, but it seemed like everything took forever. And when the food and drinks did come, half of the entrees and drinks went to the wrong people, but we just let it slide.
Wonderful food. Downstairs very noisy, but tables upstairs are spread apart with high ceilings and abundant windows—perfect for brunch.
Great Italian food on Federal Hill. I make a point of getting there when I am in town.
Outdoor seating was really good and excellent mimosas
Waitress was awesome as well as food. They didn’t rush us out. Definitely go again
Dined on a Friday night, tables are spaced and there was outside dining, we ate inside too cold for us. Calamari is delightful, fresh, crisp, fantastic sauce. Octopus with fava beans was really good. Scallops with butternut squash risotto outstanding. Fruitti de Mar was plentiful, Salmon was a good portion with a black risotto. Finished with their homemade bread pudding. Service was good and attentive. It was a great evening and we would highly recommend Massimo Restaurant as one of the better restaurants on Federal Hill.
It was absolutely amazing. It was for my boyfriend‘s birthday and they put a little birthday greeting sign on our table with little stars. Our waiter was very attentive and knowledgeable about anything we asked about. We were consistently checked on by management to see if we were enjoying ourselves. It was my first time dining there and will definitely be back.
Visiting with friends
Overall, the food was just mediocre. My plate came out lukewarm and my husbands lasagna was nothing special. This was the second time eating there in the past few months and we left dissatisfied again. We are surprised since Pane e Vino is consistently our favorite restaurant in Federal Hill and I believe Massimo is owned by the same company.
Great spot with great service. W celebrated a birthday and they had it all covered. Will definitely be going back
Our experience at Massimo was fantastic. The service was consistent, attentive & friendly. We throughly enjoyed our dining experience. The appetizers were wonderful, the entrees delicious & desert, well, it topped off a great evening!
Great food. Awesome service. At no fault of the restaurant a family with 3 very young children sat next to us. They were cute but super loud, fighting, crying etc. made it difficult to really enjoy the meal. I felt for the beleaguered parents..... probably out for a long overdue night out. But they should have hired a sitter, or maybe chosen a different a more kid friendly restaurant .
Massimo is always a wonderful experience when it comes to their food. Everything was terrific as usual. Unfortunately we were seated next to a large, very loud Birthday party. Our poor server was struggling to balance this table and her other tables. It put a bit of a damper on what was supposed to be a nicer intimate Birthday dinner. This is not a reflection on the server at all as she was doing her best, but management could have certainly been a bit more present to assist them in service, or apologize to all the other guests dealing with the raucous group, or maybe even shut the the large party off after their 4th round of shots when they were all screaming and banging the table.
We went to Massimo for Brunch and we’re not disappointed. The menu had a wide range of selections.
The restaurant is following all COVID protocols and the staff was friendly as always.
Massimo and its sister restaurant Pane e Vino have the best beef carpaccio and best lobster ravioli in the state, in my humble opinion! We also ordered the swordfish special, which included the creamiest risotto we've ever enjoyed, and also a very tasty sweet pepper sauce on the side. Everything was fantastic, except that there was no room left for dessert!
Outstanding food. Make sure you make a reservation as this is a very popular place. Staff was great. Manager was very interested in our experience.
From walking in the front door to getting our check our waitress was very attentive, helpful and pleasant. The food was outstanding, portions were perfect.
We wanted to go to a special place to celebrate my sons 21st birthday and have ability to gather together as a family in a restaurant setting after such a long break due to Covid. A fiend had mentioned Massimo to us and we could not be happier with our experience. We ended up eating indoors and they sat us at a corner table with partitions up all around us making us feel safe and giving us a sense of privacy. The table has sparkly stars and confetti on the table and there was a happy birthday sign waiting in the center of the table. Our server Benedetta was fun, attentive, and professional. The food and drink ( and we ordered plenty of each) was amazing from Squid ink pasta with lobster, to beef short ribs gnocchi, to a plump, grilled pork chop with caramelized figs served over roasted cauliflower and brown butter gnocchi. We indulged in Molten lava cake, caramel gelato and cheesecake for dessert and of course they brought my sons out with a candle and
we all sang happy birthday. We could not be happier with the fun and festive atmosphere they provided and the delicious, artfully presented food.
Great meal. Great time. Our waiter Connor was awesome! We will be back.
Outstanding meal, fantastic service, and welcoming staff to my family with 3 young children. Best Italian on Federal Hill!
Little slow to start out our waitress didn’t know she had us as a table manager stopped by and comped a round of drinks which was fantastic, food was amazing, outside dining was a good time! Valet was very helpful!
Had dinner here for my birthday and we had a great experience. Our waiter was phenomenal and the food was great. Will definitely be going here again!
We came in to celebrate a 40th birthday and we had such a great time, the table was lightly decorating when we sat down, our waiter Miz was very helpful and kind, and all the food was amazing. Someone in our party has Celiacs and they had so many Gluten free options for her which was great.
Food was AMAZING ! Service was very good but they rush the food. I would have preferred a rest between courses but they were anxious to turn the tables.
Food and service good but I feel the prices are very expensive.
Table was too small for two people. Service was just OK. We were told they were out of “house” Cabernet and sold us a 18.00 glass of wine. Unheard of.
My family loved everything about this restaurant and the food was outstanding. Definitely going back.
Excellent food and service. The only downside was that we were at a hightop table for four with five people made it very crowded.
Easter brunch. Five of us, every dish was just delicious!! Excellent options, reasonable prices. We wi definitely return👍
The brunch was perfect! Couldn't have asked for a better server and food :)
Delicious brunch food and really quiet and covid-friendly!
Very lovely place .
We enjoyed it very much
Great for celebrations .
You can order delivery directly from Massimo using the Order Online button.
Massimo is rated 4.7 stars by 2197 OpenTable diners.
Massimo does offer gift cards which you can purchase here https://providence.massimori.com/buy-gift-cards/.
Yes, you can generally book this restaurant by choosing the date, time and party size on OpenTable. Due to local restrictions, this restaurant may not be accepting reservations at the moment.