10 best Boston date ideas

Why it’s romantic: Known for its primarily Italian-American population, the North End can be summed up in one word⁠—amore. This is where you’ll discover tasty meals, flowing glasses of wine and intimate cafés with dim lighting that creates the perfect place for a smooth.

Don’t miss: Check out the coveted outdoor private balcony and its table for two overlooking Hanover Street at Tresca or enjoy the dark lighting at romantic Bricco (a picnic isn’t out of the question, when you pack up your basket from their salumeria located in the alley behind the restaurant.) After dinner, grab some sweets at Bova, Mike’s or Modern Pastry - which sends out the best pastry might be your first argument.

Why it’s romantic: Winter in the Commonwealth can be bracing, but if you bundle up and clutch a hot drink, it can be downright charming when you skate the ice on the Frog Pond. But Boston's weather isn’t always cooperative, so when the skies are looming or the temps a fright, head inside for a little playful competition...that is until things get really heated (in a good way, we hope). 

Don’t miss: There’s the tech-infused mini golf game at Puttshack, darts at Fight Club Boston, ping pong at SPIN, "links" at the brand new Five Iron Golf, or head to the pickleball mecca of Bosse in Natick. Are you and your special someone pinball wizards? Check out F1 Arcade or Versus in Boston.

Why it’s romantic: Take a chance on love with an evening at the Encore Boston Harbor. From relaxing in the co-ed lounge at the spa to hitting it big at the Blackjack table, there are plenty of spots to make memories. Don't forget to take a selfie together in front of the iconic carousel. 
 
Don’t miss: Start your date off with one of the spa’s couple rituals  - a massage lesson followed by a 90-minute couple’s balancing massage. Then treat your date to a night of wining and dining at Rare Steakhouse (New England’s only authentic Kobe beef program) or the casino's newest addition, Seamark and its refined ocean-bounty menu (there’s even a hidden speakeasy). Who knows? After a night of dancing at Memoire, you might get lucky.

Why it’s romantic: They’re based on a forbidden notion and are all about being sneaky with a whispered location. These are some dark and dreamy destinations - need we say more?

Don’t miss: 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. New on the list are Extra Dirty Cocktail Club in the North End, D16 in Back Bay, and Blind Duck on the 17th floor of Raffles Boston, or you can also check out the OGs – Yvonne’s, Wig Shop and Bogie’s Place (where you can also get a great steak).

Why it’s romantic: 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.

Don’t miss: The best night for a rendezvous is the first Thursday evening of each month, when the museum offers free admission and is open later (until 9pm). Occasionally there will be live classical music throughout the museum to enjoy.

Why it’s romantic: 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).

Don’t miss: 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.

Why it’s romantic: 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.

Don’t miss: 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.

Why it’s romantic: Promenade down Newbury Street, where you can make an afternoon of people-watching and perusing is beautiful parade of store. Walking around the brownstones of yesteryear’s Brahman Boston is quintessential urban living. Promenade down Newbury Street, where you can make an afternoon of people-watching and perusing its beautiful parade of stores. Head over one block to the Comm Ave. mall for a night time light show – the entire strip was designed in the French boulevard style.

Don’t miss:  Start at Arlington and shop all the way down to Hereford: Browsing both high-end fashion houses and budget-friendly labels (peep all the consignment stores, as well). Stop along the way for cocktails and dining, and stop in for a stroll around any of the many art galleries that pepper the street.

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Why it’s romantic: Going for a walk is nice, but up the ante with a stroll in the country’s first Arboretum, a lush expanse of florals and greenery.

Don’t miss: Stretching from Jamaica Plain into Rozzie, the 281-acre landscape has a world-renowned living collection of 15,000 plants. Walking hand-in-hand around the ponds and pathways is a full-day romantic affair, with such stops as Hemlock Hill, Leventritt Vine Garden, Rhododendron Dell, and the Bonsai Collection (particularly nice in the fall).

Why it’s romantic: The peaceful nature and glorious landscaping makes a surprising worthy date spot out of Mount Auburn Cemetery. Set on 72 verdant acres, this National Historic Landmark—the final resting place for numerous famous names—is also an arboretum and wildlife sanctuary full of winding paths, ponds and benches.

Don’t miss: The secluded dell boasts a lovely pond, and nearby Washington Tower offers inspiring views over the city and beyond. During the summer they even have the occasional outdoor movie on the grounds. 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. 

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.

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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.