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Smoked Chai Manhattan at Oak Long Bar
Photograph: Brian Samuels

The 14 best Boston date ideas

Whether it’s your first or your 50th, make date night the best night in Boston.

JQ Louise
Written by
JQ Louise
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From romantic strolls along the water, to a cultured afternoon at a museum to a lively night out, Boston is always up for the challenge of impressing your special someone. Take the pressure off planning by scanning our suggestions of the best date night ideas in Boston sure to make sparks fly. While we’re happy to play Cupid, 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.

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

Time Out Market Boston
  • Restaurants
  • Fenway/Kenmore

Show off your culinary cred by bringing your date to Boston's coolest gourmet destination. Time Out Market is a contemporary culinary hub boasting a tantalizing assortment of curated food offerings, two slick bars and lots more. Just steps from Fenway Park, Time Out Market is the perfect place to start or end a night out. 

Best Boston date ideas

  • Things to do
  • Sport events
  • Fenway/Kenmore

Take a page out of Bennifer's playbook and head to Fenway Park. Tickets in hand, trade the usual pre-game beer and sports bar scene for one of the neighborhood's sleeker spots like Eventide or the Verb. 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 that Fenway is known for in Boston. 

  • Things to do
  • South End

Sometimes slowing down for a quaint, old-fashioned picnic is the perfect date. 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.

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  • 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.

Patio hop in the Seaport
Photograph: Olivia Vanni

4. Patio hop in the Seaport

We are so fortunate to have lots of trendy patios in the Seaport these days. From the newly opened Serafina Seaport, to Lola 42, to Para Maria at the Envoy to the good-old Woods Hill Pier 4 the Seaport is spoilt for choice. Dress to impress and head to a few of the hotspots in this waterfront neighborhood. Perhaps start with drinks at Para Maria, have dinner at Serafina or Woods Hill and finish with dessert at Lola 42.  

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Go all in at Encore
Photograph: Courtesy Encore Boston Harbor

5. Go all in at Encore

Why not take a chance on love with an evening at the Encore Boston Harbor? Treat your date to a night of wining and dining at Rare Steakhouse (the only authentic Kobe beef program in New England). And then perhaps head to the nightclub upstaires, Memoire, to dance the night away. Take a selfie together in front of the iconic carousel. Who knows? Maybe you’ll get lucky.

Find la dolce vita in the North End
Photograph: Courtesy Yelp/Veronica C.

6. Find la dolce vita in the North End

The North End can be summed up in one word⁠—amore. Known for its Italian-American population, this is where you’ll discover tasty meals, flowing glasses of wine and intimate cafés. The most romantic place to dine this year is on the patio at Mamma Maria in North Square. After your meal, head across Hannover to pick up cannoli at long-time dueling eateries Mike’s and Modern. As Boston residents are split on the answer, which pastry is better might be your first argument.

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Step into the darkness at a speakeasy
Photograph: Courtesy Yvonne's

7. Step into the darkness at a speakeasy

Boston is home to a few speakeasies these days and between the dim lighting, the tasty drinks and sexy atmosphere, these are just the places to go when you want to add a little spice to date night. In the Back Bay the newest place on the block is Hecate, created by the owners of Krasi, this Greek-goddess themed bar is dark, mysterious and worth a look. Downtown, the king of bars remains Yvonne’s, housed in the former Locke-Ober property, every power broker from JFK to Mayor Menino has once sat in their now trendy dining rooms. And in Eastie, Next Door is a hidden neighborhood speakeasy where the drinks really shine. Expect over the top presentation that is sure to impress even the pickiest of dates.

  • 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).

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  • Restaurants
  • Contemporary American
  • Waterfront
  • price 4 of 4

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.

  • Things to do
  • Walks and tours
  • Waterfront
  • price 3 of 4

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.

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  • 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.

  • Restaurants
  • American creative
  • Fresh Pond
  • price 3 of 4

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. 

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  • Restaurants
  • Italian
  • Back Bay
  • price 3 of 4

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 bistro feel. Table 12 is known as the engagement table because it's often the location for locals looking to pop the question.

  • Restaurants
  • Contemporary American
  • Harvard Sq
  • price 4 of 4

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. 

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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