Dating in Boston is anything but boring. With so many fun things to do and romantic ways to explore this historic city together, you’ll never have to settle for just dinner and drinks. So whether it’s a blind date with someone you met on an app or a standing date night with your significant other, these unique date ideas in Boston, MA are sure to impress.
Get your game on in Seaport
Think you got game? Put it to the test with some friendly competition. Boston’s Seaport District has plenty of options for an action-packed night on the town. Challenge your date to game of darts and hit all the right marks. With semi-private playing areas, innovative technology, and an urban cool environment, Flight Club takes this classic dive bar game to the next level. Or go for a game of mini golf at Puttshack. Featuring four sprawling indoor courses spread across two floors, you can indulge your inner child come rain or shine. And then there’s Kings, the ultimate entertainment experience with bowling, shuffleboard, and arcade games in a retro-inspired space.
Dine with a view at Contessa
When it’s time to celebrate a special occasion, treat your date to dinner and drinks at Contessa. With elegant interiors designed by Ken Fulk and windows overlooking Boston’s Back Bay and the Public Garden, this rooftop ristorante atop The Newbury hotel offers the best views in Boston.
Enjoy cocktails and comedy in the North End
When you both need a good laugh, find some comic relief at Improv Asylum in the North End. If you’re daring, raise your hand when they ask for audience participation. If you’re really daring, sign up for improv classes and get ready to step into the spotlight. Top off the evening with an espresso martini at Bricco or canoodle over cannolis at Mike’s Pastry.
Score big with a sporting event
Looking to score? Don your team’s jersey and root, root, root for the home team! Boston is a die-hard sports city. Both Fenway Park and TD Garden are conveniently located in the heart of downtown, making it easy to catch a Red Sox baseball game, a Bruins hockey game, or a Celtics basketball game.
Not able to splurge on tickets? Sidle up to one of the many sports bars nearby. In Fenway, Bleacher Bar (aptly named) is located beneath the bleachers and offers a unique view of centerfield. Around the corner, Game On! boasts a sprawling basement where you can indulge your competitive spirit with ping pong, corn hole, and even the Official Red Sox Visitors’ bagging cage.
Go stargazing at Boston University Observatory
Don’t just gaze into each other eyes, gaze into the stars at the Boston University Observatory in Fenway. On Wednesday nights, they offer free public admission – talk about a cheap date! It’s the perfect pick-me-up when your bank account is low but your dreams are sky high.
Try bouldering and brews in South Boston
Relationship on the rocks? Work it out with a climbing session at Rock Spot Climbing in South Boston. Afterwards, head next door to Castle Island Brewing to raise your spirits with a postgame brew.
What are some of your best date ideas in Boston, Massachusetts? Share in the comments below!
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Improv Asylum is great! I’ve been there a few times and always leave with a smile in my face. In the summer I highly recommend renting a kayak and paddling the Charles!
Oh that’s a great idea! I’m going to have to give that a try as soon as the weather gets warm, thanks!
I love Boston! My brother did his Masters at MIT so I went to visit him every year! We didn’t do date stuff haha but loved going to Fenway, Little Italy, visiting Acorn Street!
Those are such fun places to visit, and would make for great date ideas as well! Thanks for sharing!
Super love all your US articles! Have harboured the craziest idea of travelling through all 50 states even though I am nowhere near that part of the Earth – will probably have to live vicariously through you in the mean time (P.S.: Your IG fall pics are stunning!😍)
Thank you so much! Please do keep following along for more adventures 🙂 What part of the world are you in? There are so many beautiful places to visit, so little time!
Love these date ideas and you described each mood perfectly! I don’t live in Boston but think I could find similar things to do in Denver!
Thank you! You’re totally right, I bet you could – let me know what you find!
These are so great ideas! I’m going with my husband to Boston for Valentine’s Day so this will be a good list to have. Top of the Hub and Prezza sound like our kinds of places.
Boston is the perfect city to visit for Valentines Day! Top of the Hub and Prezza are super special and romantic. Hope you and your husband have an amazing trip.