Best Restaurants for People Watching in Charlestown

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.

Food was magnificent! Service was outstanding! But like mist restaurants in the North End, they squeeze way too many “seats” into small space. It’s quite loud. Difficult to hear conversations at a table of 4 people. We were there for Christmas Eve so if was busy but I bet on a random Tuesday the experience would be much different and more enjoyable. I will say it was the best of the 3 North End restaurants I went to this week. I had pizza which was amazing! Better than regina. The pistachio martini was delightful!!!

This was our first time eating at this restaurant and we very much enjoyed our meal. The service was excellent, the food was great and the ambiance was nice. The only downside was we were seated downstairs in a far dining room and I had my 80yr. old mother with me. There was seating upstairs but they sat us downstairs and the stairs were very difficult for her. If you have someone who can't walk well you should request to sit upstairs. Other than this, it was excellent.

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!