The 5 Best Spots To Bring A First Date In Boston, According To A Local

Boston has a thriving nightlife scene, with plenty of establishments to fit anyone's first-date personality, from lively and energized to low-key and moody. As someone who's lived in the area for the majority of my life, my rolodex of great establishments is long, and I like to keep it current. While I might not be going on first dates anymore, I've pulled together a list of a few spots I love and know would be the perfect vibe for those nervous about picking the perfect place  (and one of them holds a special place in my heart as a first-date spot!). 

Finding the right dining setting for a first date can be nerve-wracking. What are the best and worst restaurants for a first date? Is your date more the jeans and a sweater casual type, or do they love getting dressed up and exploring the finer things in life? Perhaps they fall somewhere in between? Once you're on the date, what's the absolute worst thing to order?

For Bostonians who want to take the guesswork out of planning a (hopefully) great first date, this list contains options across multiple categories, from bars to sit-down restaurants to indoor mini-golf spots. Each one has options for tasty food and drinks, and some even play into the deep history that runs through the city, so there's bound to be something here that will suit your (and your date's) tastes, while embracing the spirit of Boston. 

First on the list is Carrie Nation, a cocktail bar and restaurant located just off of the Boston Common and right near the State House. The spot's name is an homage to a woman known as Carry Nation, who was an advocate for the temperance movement in the late 1800s. Nation was a unique figure who became famous for using a hatchet to destroy bars, and the Beacon Hill spot honors that legacy — albeit ironically.

Carrie Nation is a great first-date spot because it offers different sections for eating and drinking, so patrons have some say in what kind of experience they want to have here. For a more low-key drink, grab some seats at the bar in the front section. Carrie Nation also serves delicious American food if you're hungry (think New England clam chowder, sandwiches, and steak). 

Adventurous pairs can walk through the restaurant and around to the back — and make sure to look at the old-timey photographs that line the walls on the way. Through the red curtains is Carrie Nation's cocktail club, which it calls "Boston's Original Speakeasy" (via Carrie Nation). You and your date can sip on something from the spot's unique menu of drinks — perhaps a Carrie's Espresso, which features espresso rum, borghetti (one of the best coffee liqueurs for espresso martinis), and brewed espresso. The speakeasy format fits the bill for those looking for a livelier first date. There is often live music, dancing, and billiards games.

Another spot that offers numerous first-date settings under one roof is Ciao Roma in Boston's North End neighborhood. The North End is famous for its dueling Italian pastry shops, Mike's and Modern, and popular restaurants like Carmelina's or Giacomo's, but there are so many eateries and bars that are off the main drag and just as delicious — like Ciao Roma. It's the perfect location for a date, whether it be your first or a special celebration. Ciao Roma has both a restaurant and a smaller bar. I've been to both parts of the eatery, and each offers a different kind of vibe that you and a first date could enjoy. 

The restaurant, with tables located on the second floor, has amazing food — I'm personally a huge fan of its fusilli alla vodka — which you can pair with classic Italian antipasti like burrata bruschetta or calamari. In 2024, the eatery even had a Monday date night special, where couples could get a starter, two entrees, and a dessert for $59. 

If you're looking for a cozy spot to just grab drinks, Ciao Roma's first-floor space is the way to go. Overlooking North Square — the place Paul Revere used to call home — you and your date can snag some bar seats or head to a small table to talk over drinks. During the warmer weather months, an Aperol or Hugo spritz would hit the spot, and in the fall, the bar offers a seasonal PSL Espresso Martini featuring pumpkin cream. 

A quick train ride and short walk from Ciao Roma is Boston's South End neighborhood, where you'll find Barcelona Wine Bar. Conveniently located on Tremont Street, this Spanish tapas bar is inspired by the flavors of the Mediterranean and features an extensive menu of delicious bites, larger paellas meant to share, plus cocktails and wine.

Although it's a small chain that's not exclusive to Boston, Barcelona is a great first date spot because of the food and atmosphere. Often filled with a younger crowd both mingling at the bar and chatting at tables, Barcelona is a good choice if you're looking to have great conversation in an engaging environment. Additionally, a tapas-style eatery allows those just getting to know each other an opportunity to share and sample lots of small bites instead of committing to a more formal sit-down dinner. If you want to stay and talk for hours, keep the tapas coming — if not, you'll have an easier time chowing down and asking for the check. 

My favorite menu items include patatas bravas (one of the Spanish tapas you need to try before you die), the chicken thigh, and roasted mushrooms. Pair your tapas with a pitcher of Barcelona's delicious sweet red sangria, and you're guaranteed to have a perfect first-date meal. If you're more inclined to order a drink sans food, Barcelona also has a bar area — but keep in mind it does tend to get crowded, especially on the weekends.

This one's for the pairs who prefer a super laid-back energy for their first time meeting (and is where I had a special first date). Beantown Pub has both an ideal vibe and a perfectly accessible location. Only a few minutes walk from Boston's downtown Park Street transit station, this bar markets itself as "the only pub in the world where you can drink a cold Sam Adams while viewing a cold Sam Adams" (via Beantown Pub). It's true. Sam Adams is actually laid to rest in the Granary Burying Ground across the street.

Unlike some of the other spots on this list, Beantown is unmistakably casual. The crowd ranges from tourists stopping by after dinner to locals in jeans and sweatshirts to younger crowds grabbing their first drinks before a night out. Beantown's walls are decked out in Boston memorabilia, and there's often a sports game playing on the collection of televisions throughout the bar. You can either order drinks at the bar or seat yourself and be served at one of the many tables — the pub has an extensive list of draft beers and signature or classic cocktails. Beantown Pub serves classic bar food like cheese fries, as well as sandwiches named after Paul Revere and, obviously, Sam Adams. If the date is going well, you can challenge each other to a friendly game of pool at one of the pub's tables (though they might be occupied for hours if you go on a weekend).

My final choice is definitely more geared to those who want to do something fun and interactive on a first date, and it's perfect for people who also love some good, friendly competition. Puttshack is a national chain with two Boston locations, and the one in the trendy Seaport neighborhood offers city-dwellers indoor mini-golf alongside food and drinks. What makes Puttshack's courses so fun is that they're essentially hands-free, minus swinging your club. An automated system keeps track of your ball, how many strokes you take, and the score, all of which you'll see illuminated on a screen above each hole. Puttshack says this technology helps customers "spend less time keeping track of who's cheating, and have more time for friendly banter, prizes, and refreshing drinks" (via Puttshack).

In all, there are four different nine-hole courses to try out, and two bars to grab drinks from before, after, or even during your gameplay. Sample a fun drink from Puttshack's menu, like a delicious Cold Brew Espresso Martini or the Puttshack Paloma cocktail, made with grapefruit Paloma mix and a Tajín rim. And while you can't eat on the course, you and your date can grab a bite before or after the game. There are $7 happy hour plates Monday through Thursday (featuring the amazing loaded tots), plus a larger menu of shareables available at any time. As a note, if you're looking to avoid the family crowd, the venue is 21-and-up after 9 p.m. on Fridays and Saturdays.