There’s nothing more charming than wandering the cobblestone streets of Boston. No matter what mood you’re in, discover the most romantic ways to explore this historic city together. Whether it’s a first date with a crush or a standing date night with your significant other, here are the best date ideas in Boston, Massachusetts.
For when your bank account is low, but your dreams are sky high…
Don’t just gaze into each other eyes, gaze into the stars at the Boston University Observatory in Fenway. Talk about cheap date: on Wednesday nights, it’s free public admission!
For when it’s a special occasion…
Grab dinner and drinks at the Top of the Hub. Sitting atop the Prudential Center, it offers the best views in Boston. Grab a table by the window and watch the twinkling lights of planes flying in and out of Logan airport, or sidle up to the bar and tap your foot to live jazz music.
For when you need a good laugh…
Find some comic relief at Improv Asylum in 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.
For when you can’t afford a trip to Italy…
Splurge on an authentic meal at Prezza in the historic North End. Is the date going well? Continue on to Parla, a speakeasy-inspired eatery offering custom cocktails.
For when you’re feeling low…
(Literally) elevate your mood with a climbing session at Brooklyn Boulders. Afterwords, continue to raise your spirits with a post-game brew at Aeronaut Brewing Co in Somerville.
For when you’re looking to score…
Don your team’s jersey and root, root, root for the home team! Boston is a die-hard sports city, with all major sports teams consistently winning championships. 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 (apt to its name) 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, cornhole, and even the Official Red Sox Visitors’ bagging cage!
What are some of your best date ideas in Boston, Massachusetts? Share in the comments below and pin this post for later!
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.