Date Night Guide To Back Bay – Boston

When it comes date night around Boston, Back Bay will always impress a date (and put a dent in your wallet). For an easy way to win brownie points, follow our date night guide to Back Bay below.

Pre-Dinner Cocktails – Pinky’s

Pinky’s has a fun, energetic atmosphere that will set the right vibes for your date night. The bright chandeliers, vibrant colors, and cozy mood gives us Miami vibes right here in Boston.

Cocktails are the main focus, and their menu features creative twists on all the classics you know and love. For us, the highlight was the marshmallow espresso martini. We’ve had espresso martini variations that take it over the top creating a sugary, creamy mess. This is not the case at all at Pinky’s. Their espresso was the star of the show, while marshmallow and caramel play a supporting role.

If you prefer your liquor brown, the smoked tobacco old fashioned is the drink for you. As unappetizing it sounds, these flavors really go well together, and the smokiness adds balance to the drink.

Dinner – Faccia a Faccia

From the restaurant group that brings you LIttle Donkey, Toro, and many of our other favorite spots around Boston, Faccia a Faccia brings coastal Italian to Back Bay.

Unlike typical American-Italian that will leave you needing a nap after the food, Faccia a Faccia’s fare is fresh and light. The grilled octopus had a tenderness that melted in our mouth and featured nice chunks of guanciale. Their homemade pasta was also top-notch. It had a chewiness that you only get from fresh-made pasta. The rigatoni were massive, which helped capture all of the sauce in the carbonara.

Also, the basement features a wine bar with natural wines which are perfect for a post-dinner drink.

Dessert – Contessa

There isn’t a better way to end date night than rooftop views of Boston. Contessa books out for months in advance, but if you are lucky enough, you can get a seat at the bar.

When we first went here we were just planning to stop in for a drink. But when the person next to us ordered a Boston cream pie, we knew we had to order it too. This decadent creation is a tower of cream, chocolate, and shaved chocolate with a cookie on the side. Each bite featured a layer of cream and thick rich chocolate. This is easily one of our top desserts in the city.

At the bar you can enjoy $20 cocktails which taste that much better with the view. Overall, Contessa is an experience that will impress any date, and works as the perfect end to any Boston date night.