Best Restaurants for People Watching in South End

This space has such a great vibe! Will definitely need to come back for dinner!

From the moment we stepped into Contessa, we were greeted with the warmth and charm that only an exceptional Italian restaurant can offer. Located in the heart of Boston, this dining gem delivers an unforgettable experience, from its stunning ambiance to its mouthwatering cuisine. The setting itself is nothing short of spectacular. The stylish interior, complete with elegant lighting and cozy seating, creates the perfect atmosphere for an intimate meal or a celebratory dinner. The breathtaking views of the city from the rooftop, especially with the adjacent park lit and sparkling for Christmas, made every bite of our meal feel even more special. The menu at Contessa is a true tribute to the flavors of Italy. We began our meal with the freshest antipasti of Tonnato Crudo. Each bite of this dish consisting of thinly sliced raw tuna, artichoke hearts, and anchovy was a burst of flavor and authenticity. For the primi course, we shared the Spicy Lobster Capellini. Wow! Pasta was cooked perfect al dente; the lobster sauce was amazing. Nice small chunks of lobster throughout. For the main course, we split the Grilled Mediterranean Branzino. Believe me, it was cooked to perfection, flaky and full of delicate flavors. Dessert was the grand finale. The tiramisu was light, airy, and just the right amount of sweet. It was a divine ending to what was already a remarkable meal. What truly sets Contessa apart, though, is the service. The staff was attentive, knowledgeable, and eager to ensure our experience was nothing short of flawless. They offered wonderful wine pairings and gave great recommendations, making us feel like VIPs throughout the evening. If you’re looking for an elevated Italian dining experience in Boston, look no further than Contessa. Every detail, from the food to the ambiance to the exceptional service, makes it a must-visit destination for food lovers and anyone looking to enjoy an unforgettable meal.

My husband took me to the chestnut hill location for my bday and our food was amazing. Since we had family in town for the holidays, we decided to go to the Tremont st location. It did not disappoint. The escargot were as good as any I had in Paris, a lot of flavor. We also got the French onion soup which was delicious and fitting for a cold Boston evening. Lotsssss of cheese! Our entree was a duck and mushroom risotto that they split for us- also very good. We will definitely be back but probably for special occasions as it is on the expensive side.

When you arrive you are greeted by the hostess and almost immediately seated. We were quickly greeted by by PETER P. Peter was absolutely amazing. We were celebrating a birthday and he really made sure we would enjoy our experience. Peter gave amazing recommendations on both beverages and meals. Only complaint would be that my steak was cooked wrong but without hesitation, Peter came over and had them remake it. The manager came out and apologized and asked if the new steak was cooked to my liking. At the end, Peter brought out a mini cake and shared lots of stories with us. Overall, service was spectacular !! constantly checking in on us and having small talk. My significant other and I are definitely looking forward to having lunch again and I will definitely be asking for Peter !!

This is the second time I've been and it was as good as the first time! This is such a great place, excellent food, great service, cool vibe, no one rushing you, can't recommend this enough, you have to experience yourself, highest recommendations!