Best Restaurants for People Watching in Fenway–Kenmore

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

Second time in and our party of five had a fantastic experience, equal parts food, drink, service (especially waitress with impeccable timing) and ambience. Octopus, endive salad, lamb chops, filet, duck club, burgers - all delicious and prepared exactly as requested, including GF accommodation. A Manhattan heavy on specifics was expert-crafted, sub-zero cold and delivered at the perfect time. Great music heavy on classic indie played loud enough to hear but low enough to talk normally. We’ll be back for sure!

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.

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!

The best French toast!! Lovely wait staff. Great food. Loved everything, thank you!