14 best Boston date ideas

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.

Winter in the Commonwealth can be bracing, but if you bundle up and clutch a hot drink with your mittens, it can be downright charming. One of the best winter activities, hitting an ice rink, is beloved by both locals and tourists, and the Hub has no shortage of rinks fit for all levels. Grab your partner in crime and hit one of our favorite rinks. 

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 eatery—and 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. 

Sometimes slowing down for an old-fashioned night in 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 home for the perfect night in for plenty of cozy vibes. 

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.

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.

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.

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 later—and keep a special eye out for its Third Thursdays, when the evenings boast themed events featuring resident and visiting artists in all disciplines).

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. 

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 yourself—on 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.

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.

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-trip—on the outbound stretch, stop off for selfies while exploring North Cambridge’s Alewife Brook Reservation, Arlington’s Great Meadows and Lexington’s Battle Green. 

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.

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 shawarma—just save room its celebrated sweets, like the sesame toffee blondies and raspberry rose turnovers.