Date Night Guide to the North End – Boston, MA

When it comes to romantic date nights in Boston, it’s pretty hard to beat the North End. With an endless array of charming Italian restaurants, it can look like a scene out of “The Fox and the Hound.” We’ve already shared our last minute date night recs for the North End for those procrastinators among us– but if you are a planner, then in this guide we share the best of the best.

STOP 1: Drinks at Farmacia

Inconspicuously located off of North Square, you might walk right by Farmacia if you’re not looking. This intimate 9 seat cocktail bar takes their drinks seriously, as all of their syrups, juices, and infusions are made in house. All of their juices are cold-pressed, so you can get your daily serving of fruits and veggies while catching a buzz. It is their meticulous care for fresh, quality ingredients that make this not just another bar to get a vodka soda, but a true luxury experience.

Obviously this spot is pricey, but for that special date night, it is well worth it. Plus, with a rotating seasonal menu there are new drinks every time we go.

STOP 2: Dinner at Giacomo’s

With what seems like an endless amount of options for dinner in the North End, it can be overwhelming picking where to go. While there are plenty of good spots to eat, very few are exceptional. We have written about Giacomo’s before, but felt like it deserved another call out in this guide as well, since it checks all of the boxes needed to impress your date. The old brick walls, the small dining room, and the open kitchen transport you to a small European restaurant in which the recipes have been passed down from generation to generation. Fresh pasta is a minimum for any quality spot in the North End, but what separates Giacomo’s from the rest of the pack is their sauce game. The “fra diavolo” is a spicy lobster red sauce, their “Giacomo” is a creamy lobster red sauce, and our personal favorite (which is the best of both worlds) the “Fracomo,” is a combination of the two. These robust and flavorful sauces elevate any dish, whether you are keeping it simple with some chicken parm or getting one of their classic seafood-filled pastas.

And speaking of, if you are looking for lobster, you won’t get a better combination of New England and Italy than the homemade fusilli with chunks of lobster meat and shrimp– all smothered in their spicy, creamy, lobster red sauce.

STOP 3: A Night Cap at The Flamingo

Whether we’re already in the North End or just wanting to go out somewhere,  The Flamingo is one of our favorite spots for a drink. We like to think of Flamingo as a Southie bar, but for those over the age of 25.

There won’t be a cover, but there may be a short wait. It’s going to have good music, lively energy, and you will actually have room to move around. If you can get a table, then there are fun bar games to play as well. Also, in the back you might notice a secondary line to the upstairs area which can be a bit more lively than the first floor.