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Isabella Stewart Gardner Museum
Photograph: Courtesy Isabella Stewart Gardner Museum/Nic Lehoux Isabella Stewart Gardner Museum

The 13 best Boston date ideas

Treat someone special to a memorable date night with these fun activities and shared experiences

By Olivia Vanni, Linda Laban and Eric Grossman

Looking for date ideas in Boston? With so much to do and see around the Hub, the only limit is your imagination. We're here to play cupid and provide you with a range of thoughtful outing options that are sure to spark romance and maybe even score you some bonus pointsfrom low-key picnics filled with gourmet grazing to an extravagent stay at the spa. If none of these strike your fancy, you could always combine one of the best things to do in Boston with a meal at one of the most romantic restaurants in Boston. Just remember: If nothing else, get out of your comfort zone, dress up a little, and—for one entire evening—stay off your cellphone.

RECOMMENDED: Full guide to the best things to do in Boston

29,000 sq ft of the city's finest cuisine, cocktails and culture

Time Out Market Boston
Photograph: Eva Sakellarides

Time Out Market Boston

Restaurants Fenway/Kenmore

Show off your culinary cred by hosting a date at Boston's coolest gourmet destination. The contemporary culinary hub boasts a tantalizing assortment of curated food offerings, two slick bars and lots more. There are enhanced safety protocols and plenty of seating—both indoors and on a lovely, spacious patio.

Best Boston date ideas

ICA Watershed
Photograph: Courtesy ICA/Florian Holzherr

1. Dive into art at the ICA Watershed

Things to do East Boston

Venture across Boston Harbor for an immersive experience at the ICA Watershed. The Institute for Contemporary Art’s satellite gallery is located in an immense, previously condemned industrial building in East Boston’s Jeffries Point neighborhood. The 15,000-square-foot space features a regular rotation of elaborate, large-scale installations, including its upcoming exhibit from Firelei Báez, where the artist will transform the space into the site of an ancient ruin. To round out your date, we suggest exploring all that this gallery has to offer before cracking open a cider at Downeast next door, grabbing a braised lamb shank pie from KO and then sitting by the shipyard for the most spectacular view of the Boston skyline.

Odyssey Cruises Boston
Photograph: Courtesy CC/Flickr/Larry Lamsa

2. Cruise the Harbor

Things to do Walks and tours Waterfront

Departing from lovely Rowes Wharf, Odyssey provides the ultimate waterfront dining experience with its dinner cruises around Boston Harbor. These evening excursions include a three-course meal and live music (usually a singer and guitarist playing low-key rock and pop hits). After dinner, a DJ gets the party going, so you can show off your moves—and potentially embarrass yourselfon the dance floor. Head out on the deck to watch the sunset or see the city lights shining against the water for some real rom-com-worthy ambience.

formaggio kitchen
Photograph: Sarah Bentivegna

3. Slow down with a South End picnic

Things to do South End

We are all for keeping it quaint and having an old-fashioned picnic. We suggest you enjoy life’s simple pleasures in the South End, starting with a stop at Formaggio Kitchen’s Shawmut Ave storefront to stock up on the finest snacks. Grab a selection of the shop’s imported cheeses and cured meats, house-made charcuterie and artisanal bread or, for a heftier blanket spread, get some of the kitchen’s daily sandwiches and prepared salads to go. Bring your gourmet haul back to your stoop or to a nearby greenspace, like Titus Sparrow Park, where you can eat while enjoying the perfect view of The Pru set behind Boston’s beautiful brownstones.

4. Catch feelings and throw axes

Things to do

Fulfill all of your wildest lumberjack fantasies with a datenight at Revolution Axe Throwing. This Everett spot offers everything you need for a romantic axe-throwing outing, including expert instructors who can help anyone who’s never chucked a weapon at a wooden target before. Hour-long reservations are available for groups of six people or fewer, and, after you’re done wielding sharp objects, you can head over to one of the many nearby breweries—Night Shift, Aeronaut or Bone Up—to finish your night with a draft.


5. Walk the waterfront and rest with a beer

Restaurants Contemporary American Waterfront

Boston is "America's Walking City," so lace up your sneakers and stroll the scenic Harbor Walk. Work your way along the waterfront, over the Fort Point Channel and into Seaport, where you can take a break and watch the boats go by from Fan Pier. Once you return to the downtown, follow the Rose Kennedy Greenway and see a series of modern art installations framed by a perfectly manicured landscape. To end, give your feet a rest and rehydrate at Trillum's Beer Garden on The Greenway—you've earned it.

Isabella Stewart Gardner Museum
Photograph: Courtesy Isabella Stewart Gardner Museum/Nic Lehoux

6. Visit Isabella’s house

Museums Art and design Mission Hill

The Isabella Stewart Gardner Museum may not the biggest of Boston’s museums, but it is certainly the most romantic. Stroll amongst the charming, art-adorned rooms before taking a breather in the flower-filled courtyard, where there’s plenty of space to concentrate on your date. The best night for a rendezvous is Thursday, when the museum is open laterand keep a special eye out for its Third Thursdays, when the evenings boast themed events featuring resident and visiting artists in all disciplines).

Mandarin Oriental Boston
Photograph: Courtesy Mandarin Oriental Boston

7. Relax in luxury at the Mandarin Oriental

Hotels Back Bay

For a special occasion that calls for a next-level date, splurge on The Spa at Mandarin Oriental’s couples suite. This space is the size of an apartment and screams luxury, with its lavish marble bathroom boasting a massive soaking tub and sauna. The separate, Asian-inspired treatment room is equally spacious and full of natural light. This packaged experience includes a personalized time ritual or signature spa treatment and, once you've reached a state of pure relaxation, we suggest capping everything off with an exquisite dinner at the hotel’s Bar Boulud.

Photograph: Courtesy Sofra

8. Take a peaceful stroll in Cambridge

Restaurants Contemporary American Harvard Sq

There’s nothing more romantic than death, just ask Romeo and Juliet. Seriously though, Mount Auburn Cemetery is a worthy date spot. Set on 72 verdant acres, this National Historic Landmark—the final resting place for numerous famous names—is also an arboretum and wildlife sanctuary. The secluded dell boasts a lovely pond, and nearby Washington Tower offers inspiring views over the city and beyond. After your walk, refuel at the nearby Sofra Bakery & Cafe, where you can share a meze platter, cheese borek and shawarmajust save room its celebrated sweets, like the sesame toffee blondies and raspberry rose turnovers. 

Photograph: Courtesy Talulla/Wayne Chinnock

9. Break a sweat, then chill by Fresh Pond

Restaurants American creative Fresh Pond

Riding the Minuteman Bikeway doesn’t have to be a race, but it can be. For an active date idea, bike the 11-mile route from Bedford to Fresh Pond in one go. True fitness junkies can make it a round-tripon the outbound stretch, stop off for selfies while exploring North Cambridge’s Alewife Brook Reservation, Arlington’s Great Meadows and Lexington’s Battle Green. If you're riding one-way to Fresh Pond and aren't too disheveled from your adventure, finish with dinner at nearby Talulla. If you're simply too sweaty, you can always stop by this tiny Italian spot and order your carbo-load to go. 

10. Get chic in the Back Bay

Restaurants Italian Back Bay

Promenade down Newbury Street, where you can make an afternoon of people-watching and perusing its beautiful parade of stores. Start at Arlington and shop all the way down to Hereford: Browse the shelves of Newbury Comics, purchase artisan glassware at Simon Pearce, and drop a hint or two while eyeing rings at Shreve, Crump & Low. Make one last stop for drinks or dinner at Sonsie, a Back Bay mainstay with a cozy, low-lit dining room that exudes a French bistrot feel. Table 12 is known as the engagement table because it's often the location for locals looking to pop the question.


11. Go boho in Central Square

Restaurants Italian Harvard Sq

Show just how hip you can be with some Central Square escapades, starting with dinner at Pammy’s. This modern trattoria sits right on Mass. Ave. and offers a menu of handmade pastas, globally influenced Italian dishes and tasty craft cocktails. Sit side-by-side at the vintage communal table or huddle by the white tiled fireplace as you split plates—the perfect excuse to get closer. After dinner, walk into the heart of Central Square and head down Graffiti Alley before checking out a band—or a comedy night or belly dancing—at the Middle East.

AMC Loews Boston Common 19, Movie theaters, Boston
Photograph: BWChicago

12. Put on the Ritz with dinner and a movie

Movies Boston Common

OK, so you have tickets to a must-see flick at the AMC Loews Boston Common. Now take that movie night to the next level by adding dinner for two at Artisan Bistro, the Ritz-Carlton’s chic-casual restaurant. Have drinks at the elegant, horseshoe-shaped bar or grab a bite on one of the comfy couches near the fireplace. The AMC is connected to the Ritz-Carlton, so just ask the staff to point out the secret door that'll lead you to the theater.

Fenway Park, Sights and attractions, Boston
Photograph: Elan Fleisher

13. Score some romance at Fenway Park

Things to do Sport events Fenway/Kenmore

Perhaps its a Boston thing, but many a local will tell you there are few places more romantic than Fenway Park. So, tickets in hand, nix the usual pre-game beer and sports bar scene, and instead head to one of the neighborhood's sleeker spots like Eventide or Audubon. If it's a particularly special occasion and you have money to burn, you can rent out Fool's Errand—that's Tiffani Faison's 400-square-foot private eateryand have it all to your self. Then, it’s happily off to Fenway Park, where you can cheer on the Sox and enjoy the buzzing energy of the bleachers.

More cool things to do around The Hub

The 50 best things to do in Boston

Things to do

We’re all about making the most out of what's left of 2020. (Good riddance!) Temps are dropping, but there are still plenty of cool things to do, albeit carefully, while safely getting some fresh air. Among the best things to do year-round in Boston are plenty that take place away from the elements, but given the current conditions, options like awesome hiking, sunny beaches, fun cruises, and outdoor dining should move to the top of your list.

Given the ever-changing nature of government rules and restrictions, not everything listed here might be open to the public — remember to always confirm plans with the venue in advance.

No matter where your interests lie, you can always find something to get excited about in the Hub. The best things to do in Boston run the gamut—from seriously fun to awesomely educational. Looking for culture? Spend a day exploring Boston museums. Hungry? You've come to the right place. There are tons of amazing restaurants in Boston that highlight the city's rich and diverse culinary landscape. We've searched all across the city to assemble this list of the best things to do in Boston. Follow it and never get bored here again.

Done something on this list and loved it? Share it with the hashtag #TimeOutDoList and tag @TimeOutEverywhere.

You can also find out more about how Time Out selects the very best things to do all over the world, or take a look at our list of the best things to do in the world right now.


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