15 Great Boston Dates To Go On Right Now

Here’s how to warm up this winter.

There could not be more pressure to come up with an original date idea right now, what with our COVID-related limitations and our general malaise. This goes double in the cold-weather months, when you can no longer default to picnicking on a grassy knoll. And yet, Valentine’s Day looms. For the sake of the day and for your sanity, don’t resort to another night of takeout in your PJs. Even in the dead of winter in the middle of a pandemic, Boston can still surprise with its couple-friendly excursions. We’ve rounded up ideas for you and your paramour to enjoy all day or all night long.

Try your legs at night skiing

Canton, Pittsfield
Did you know that Blue Hills is just a few miles south of Boston proper and is even accessible by public transit? Not only that, but tickets after 5 pm are just $30 and still grant you four hours on the slopes thanks to the ski area’s flood lights. Or head to Bousquet Mountain in Pittsfield and get a flex pass for after 5 pm, which is just $24 in advance. If you crash, though, be sure to crash into each other’s arms.

Indulge in a staycation

Various locations
Our local hotels are doing their damndest to keep romance alive even in the middle of a pandemic. In-town spots like YOTEL Boston, The Whitney, The Envoy, The Mandarin Oriental, Loews, and The Liberty are pulling V-Day packages that are well-priced, romantic as hell, and still prioritize safety. Or prioritize the fireplace experience at either The Bostonian Boston or The Taj Boston. Or you could always book a local Airbnb.

Relax and drink outside

Various locations
Betcha didn’t know that alfresco drinking options are still alive and well. The Sam Adams outdoor area has been transformed into a winter oasis with heat lamps, Alcove Boston is doing s’mores and hot chocolate by its fire pit, and Arsenal Yards is doing weekend Fireside Hangouts with live local musicians.

Take a walking tour of the city

Various locations
There’s two ways to go: Download any number of the city’s self-guided tours, from the two-and-a-half hour Freedom Trail tour to the lesser sung Black Heritage Trail or Women’s Heritage Trail, and walk then alone, together; or just wing one of them without any recorded guidance. Either way, it’s free, it’s educational, it’s outdoors, and it’s great nerdy fun.

Learn a new semi-obscure sport together

Ah, curling—the sport we fall back in love with every four years during the Winter Olympics. But you don’t have to wait until Beijing next year—the curling lanes over at Snowport are open daily for  30-minute play slots.

Slip and slide your way through the Ice Castles

Lincoln, New Hampshire
Did you know there are such things as icicle farmers? And that they spend months “growing” icicles in the now-annual construction of a massive, brightly lit, interactive ice fortress? Think of it as a more romantic version of Superman's ice fortress.

Spend an afternoon at the Museum of Fine Arts

Once again open Wednesday-Sunday from 10 am to 5 pm, the Museum of Fine Arts is back for those that have been missing getting lost in the world famous exhibits. Tickets will cost you $25 per person without a membership but only $5 on Wednesday from 3-4 pm. Heads up, you’ll have to get your tickets online first to once again limit capacity.

Explore the many shops and food stops in Union Market 

Union Square
A quaint courtyard in the heart of Union Square, Bow Market has just about everything you need for a fulfilling first date, including outdoor dining, a brewery and room for some window shopping. With social distancing guidelines in place, you can safely browse the outdoor market and grab small bites and brews for you and your plus one.


Or pick up rounds of hot chocolate L.A. Burdick

Copley and Harvard Square
A magical spot lined with endless treats, L.A. Burdick is a memorable destination and go-to for a quality cup of hot chocolate as the weather continues its deep freeze practices. Located right in the heart of Copley and Harvard Squares, this spot is known for steaming mugs of hot drinks (and handmade chocolates), which you can grab before a wholesome stroll.

Take a stroll through the city’s famous streets

Beacon Hill
Sometimes simply walking throughout one of Boston’s favorite neighborhoods does the trick. Explore Beacon Hill (at night for extra ambiance) and take a peep at the brownstones for an easy going but surprisingly charming time. With little shops and restaurants along Charles Street, you’ll have plenty to browse and plenty of sights to help strike up conversation. And if a fresh blanket of snow happens to complete the tableau, so much the better.

Pick up a meal kit from your favorite local Boston restaurant

Multiple locations
Feeling adventurous? Well, the type of adventure that you can pair at-home with a glass of wine, that is. Look no further than to Boston’s local restaurant scene for inspiration. You can pick up DIY meal kits from Fox & the Knife, Coppa’s “To Cook at Home” options and everyone’s top spot for ramen, Yume Wo Katare. Or explore the new meal subscriptions from the likes of Forage, Shy Bird, and Sycamore.

Slurp one-buck shucks

Multiple locations
Are they aphrodisiacs? No, not so much. But the placebo effect has to be worth something, especially when so many spots around town offer $1 bivalves, from Southie’s Lincoln to Charlestown’s Monument Restaurant & Tavern. For a complete list, check out our list of the best oyster bars around Boston.

Catch a virtual screening of a cult classic

Coolidge Corner
The iconic and ideal date destination Coolidge Corner Theater may still be closed for showings; however, you can still enjoy virtual screenings of cult classics for a small price. By showing a little support, you can look forward to more date nights and buttery popcorn in the future.

Swing by the seals

Financial District/Waterfront
While you’re out and about downtown, enjoy one of the city’s greatest simple pleasures: the outdoor harbor seal exhibit outside the New England Aquarium. If you’d like to get a closer look at aquatic life, the aquarium is once again open, but you’ll have to purchase tickets ahead of time to limit capacity.

Take a cooking class without leaving the comforts of home

You love the idea of “trying new things,” but there are also times you’re fine with staying put, especially now. Well, Cozymeal lets you book virtual cooking lessons with some of our great emerging chefs—no changing out of your (work from home) sweatpants required.

Pick a fresh bouquet of flowers

On a local farm kick? Land’s Sake in Weston has pick-your-own-flowers, vegetables, and herbs perfect for your fall activities list. While you’re there, you can pick up some fresh goodies from the farmstand including squash, apples, and a pumpkin you can later carve together.

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Jillian Hammell is a contributor to Thrillist. Follow her on Twitter and Instagram.
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