The 15 best Boston date ideas

These Boston date ideas will wow your paramour with romance, creativity and originality

Photograph: Mark Thayer

Tired of dinner and a movie? So are we. Enter the best Boston date ideas: creative and memorable ways to spend time with your significant other that don’t solely include visits to the best restaurants in Boston and the best wine bars in Boston. From brewery tours to nights at the museum, these exciting outings are sure to impress your loved one. After all, a meal at one the most romantic restaurants in Boston becomes that much more exciting when reminiscing about the time you went rock climbing together.

Best Boston date ideas


A Night of Skeeball at A4cade

What’s more bonding than throwback arcade games with a side of grilled cheese? The Area Four team has struck again, this time with a speakeasy arcade filled with '80s classics (Galaga, Ms. Pacman) and a distinctly grownup cocktail menu that includes the There’s No Crying in Skeeball drink. As for that food menu, try a couple of gooey wonders from Roxy’s Grilled Cheese with a soft-serve chaser.

Central Sq

Day and evening at the Museum of FIne Arts

You probably know some of the details: the MFA houses a globe-spanning collection encompassing 450,000 objects that include Impressionist and post-Impressionist paintings, world-famous Egyptian art pieces and more. But your date won’t be restricted to passive browsing: couples can attend lectures, film screenings, group gallery tours and adult art classes.


See Shakespeare on the Common

Come summer, Boston’s favorite way to commune with the Bard is in the park, on a blanket with a tapas spread and a thermos of something that totally isn’t wine (wink). Claim your partner and then claim a grassy spot on the Boston Common to check out the Commonwealth Shakespeare Company's near-nightly productions of the playwright’s best works. Just set up your seats early or risk crushing your sweetheart’s expectations.

Beacon Hill
Conquer the Minuteman Commuter Bikeway together

Conquer the Minuteman Commuter Bikeway together

The couple that sweats together, stays together. Stretching from Cambridge to Bedford, the 11-mile Minuteman Bikeway is a great way to check out Greater Boston’s outer boroughs on a bicycle made for two. Built on a former railway, it’s also open to rollerblading, jogging, walking—anything sans motor, basically. There’s also plenty to see along the way, including Alewife Brook Reservation, Spy Pond and Arlington’s Great Meadows, plus lots of cafés that will satisfy any mid-date caffeine craving.


Stargaze at Coit Observatory

Cheesy, yes, but also totally, undeniably romantic. Every Wednesday night (weather permitting), Coit Observatory at Boston University opens up its facilities for free public viewings of the stars. They start at 8:30pm, last about an hour and promise to help you and your companion distinguish your Andromeda from your Milky Way. Afterwards, you have your choice of cheap eats along the Brighton stretch of Commonwealth Ave.


Discover a lost world at the Mapparium

Calling all geography nerds: The Mapparium, the world's largest walk-in globe, is among the city's quirkiest landmarks. It’s essentially a three-story model of the globe built to scale; the perfect sphere runs 30 feet in diameter and can be crossed by means of a glass bridge that bisects its interior. Inside, sound bounces off the globe room's non-porous glass walls, amplifying it ten-fold—which means that whispered sweet nothings from your partner across the room register directly in your ear.


Visit the Boston Public Library (seriously)

Surprise your date with a multi-tiered day of culture at the Boston Public Library. This would be ground zero for architectural geeks (the original wing was designed by Charles McKim in 1895) and literature nerds. But it’s also a hidden arts haven, given the paintings by John Singer Sargent upstairs and jazz courtyard concerts in the summer. Also expect a rather surprising dining scene: The Courtyard Restaurant offers a full afternoon tea service, and both the Newsfeed Cafe and the Map Room do breakfast and lunch.

Back Bay

Scope out seasonal blooms at the Arnold Arboretum

Stopping to smell the roses is one of the oldest—and most effective—moves in the book. In May, the lilacs are in full fragrant effect, but there’s no bad time to check out the 15,000 plants and 4,000 trees that blossom throughout the year at the Arnold Arboretum. An even more detailed suggestion: Take a leisurely hike up Hemlock Hill, enjoy a pre-packed picnic under a tree and look out over the city skyline.

Jamaica Plain

Take a tour of the Sam Adams brewery

For a city that’s often hamstrung by booze-related blue laws, Boston sure has a fine collection of breweries and brew-centric outing opportunities. A 45-minute tour at the Samuel Adams brewery is the perfect no-commitment first date. The free tours (there is a $2 suggested donation) run daily and let participants taste the malts, smell the hops and sip a few brews. If your companion is an early riser, try suggesting the 9:40am Morning Mash In tour, which includes a special tasting.


Make your move at Knight Movies

Looking for a cheap, creative and cozy date night? Knight Moves Cafe dubs itself “your living room away from home,” which means you’re getting off your couch but not outside of your comfort zone. Ten bucks on the weekends earn you unlimited access to the massive board game library. You can BYO food or booze for a $2 fee at the Brookline outpost, but both spots serve a full menu of coffee and tea.

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