The Best (Not Lame!) Ways to Spend Valentine’s Day in Boston, According to Boston Magazine Staffers

Here's where to bring your date, your pal, or even yourself.

If you ask us, the stakes are always too high on Valentine’s Day. There’s immense pressure to have an amazing time, yet a lot of the events happening around town feel so…lame.

Instead of striving for perfection, relax and savor the day—and night—Boston magazine-style. Our writers and editors know how to have a good time in this city like nobody else. Ahead, find recommendations from eight staffers on ways to spend Valentine’s Day in Boston.

Nothing says romance like the library. (I mean it.) A Valentine’s Day well spent starts with the Boston Public Library’s art and architecture tour. Stroll through one of Boston’s best buildings for an hour, learning about the genius of two very different designers: Charles Follen McKim and Philip Johnson. The tour also points out some of the BPL’s jaw-dropping art that’s hidden in plain sight. (Did you know there are works by John Singer Sargent adorning the walls?)

Either before or after the tour, it’s imperative to order two hot chocolates at the Map Room Café. They’re best enjoyed in the courtyard, so bundle up. If you’re feeling fancy, there’s also the option to sit for high tea in the Courtyard Restaurant. Romantic, indeed.

—Madeline Bilis, Associate Editor

Photo by Heather Pasquazzi

While I waited three hours for Insomnia Cookies to deliver an ice cream sandwich to my doorstep last year (only to be let down by a soupy mess), this Valentine’s Day I’ll be sitting in the audience of an Improv Asylum show. The troupe’s Main Stage performance promises 90 minutes of improv and sketch comedy and a whole lot of laughs. Be warned: This is not the place to romantically nestle up against your significant other (after all, you are in a basement under Hanover Street’s CVS). If you are one for PDA, don’t be surprised when the cast mockingly bases their final sketch off of you and your partner. Afterward, I’ll head down the street and brave the crowds at Mike’s Pasty to order a gelato. No melted treats or bowls of disappointment this year!

—Michaela Quigley, Associate Research Editor

Photo by Jonathan Beckley

I’m not one to crow that Valentine’s Day is an artificial “Hallmark holiday.” It sounds too bitter, like the heart-shaped chocolate boxes that still linger on clearance-sale shelves in late February. But let’s be real: Unlike personal anniversaries, V-Day is indeed pretty contrived—so it’s most fun to celebrate with tongue planted firmly in cheek. (Your own or someone else’s.) Subvert humdrum heteronormativity with a drag show at deliciously dive-y Jacques Cabaret—or, this year, with “Heartbreakers & Heartthrobs: A Drag Kings Valentine’s Day” (starring Throb Zombie and Whorey Feldman, among others), the latest installment of a sporadic drag series at the Museum of Science planetarium. Also titillating: Unleashing your inner Bettie Page with a burlesque lesson—Burlesque Boston has ‘em—or grabbing a seat for “Tap That: Swipe Right on Rogue Burlesque,” the tassel-shaking troupe’s dating game-inspired show at gay bar Club Café on Saturday, Feb. 16.

—Scott Kearnan, Food Editor

Photo courtesy of La Voile

My plan this year is to skip the crowded, overly pricey prix fixe dinners and enjoy a leisurely Valentine’s lunch instead at La Voile on Newbury Street instead. The classic French brasserie is cozy, romantic, and makes a mean duck à l’orange. In the past, my husband and I have also picked up dry-aged steaks from Savenor’s and sea scallops from New Deal Fish Market and cooked up the ultimate surf-and-turf feast at home.

—Brittany Jasnoff, Executive Editor

Photo by Lisa Weidenfeld

Grab a cup of coffee and walk around one of the city’s fine cultural institutions. There’s a bounty of options here, whether you want to make faces at some funky fish at the Aquarium (which is where Ron the sea lion lives, by the way), browse the vast array of taxidermied critters at the Harvard Museum of Natural History, or opine on the latest modern works at the Institute of Contemporary Art. Wherever you end up, you’ll find plenty to talk about, and best of all, you can check out of the “book dinner at the hippest restaurant in town” rat race.

—Lisa Weidenfeld, Senior Digital Editor

Photo by Rachel King

My wife and I have tested the limits of the you-can-sample-anything-in-the-store policy at Allium Market in Coolidge Corner recently. So it’s the least we can do to show up and support what is, in our opinion, the best cheese et cetera shop in Boston on Valentine’s Day. We’ll be there at Allium’s ticketed chocolate, cheese, and wine class, where you allegedly get to eat and drink five varieties of each and also take some home afterward. It’s romantic, there are snacks, and there’s no twinge of guilt for excessive taste-testing. That’s amore, folks.

—Spencer Buell, Staff Writer

Photo by Emily Sotomayor

It’s completely possible to have a special, elegant, sit-down dinner on Valentine’s Day in Boston. I’d simply advise making a reservation, keeping in mind that the restaurant is likely to be busier than usual, and tipping well. Enjoy! But, my partner’s and my preferred V-Day speed is a casual, low-key dinner—I’m thinking Eventide Fenway for oysters, Oxbow, buns, and a brown butter soft-serve to share—followed by a rock show at the Sinclair, Great Scott, or the ‘Dise. To us, nothing says romance like fancy bar food and noisy music.

—Jackie Cain, Deputy Food Editor

Photo by Amanda Lewis

À la Leslie Knope, I’m all about Galentine’s Day. For those who are unfamiliar, the holiday is best described in Knope’s own words: “Every February 13th, my lady friends and I leave our husbands and our boyfriends at home, and we just come and kick it, breakfast-style. Ladies celebrating ladies. It’s like Lilith Fair, minus the angst. Plus frittatas.” Instead of paying a visit to Pawnee’s famed JJ’s Diner, though, we’ll hit up The Breakfast Club, an ’80s-inspired dining car in lower Allston with the fluffiest, tastiest pancakes around and sprinkle-rimmed milkshakes that are a true work of art.

—Rachel Kashdan, Staff Writer