Your Guide to the Most Romantic Valentine’s Day in Boston

Looking for love in Boston? From perfect restaurants for a rendezvous to swoon-worthy date ideas, here are 20 ways to meet—and keep—your match.

Share rare and romantic sunset views with Helicopter Tour Boston. / Photo by Wayne Dion

One-of-a-Kind Dates

For daredevils
Go indoor skydiving

Adventurous lovebirds can take their relationship to new heights (literally) while “flying” and flipping inside a vertical wind tunnel at SkyVenture, an indoor-adventure facility just over the Granite State border. There’s also indoor rock climbing and surfing to get your pulse pounding.

For creative types
Craft your own rings

Forge memories making matching jewelry—including silver, gold, or platinum engagement or wedding bands—during custom workshops at Stonybrook Fine Arts. The Jamaica Plain metalworking and sculpture school will even coordinate a post-date tasting at the neighboring Sam Adams brewery, should you want to toast your beautiful new pieces.

For long weekenders
Speed off in über-luxury

Your parking days are probably behind you. But whizzing away on a romantic weekend in one of Gotham Dream Cars’ exotic rides (including rare rentals like the Lamborghini Aventador, which sells for nearly half a mil)? That still gets the motor humming.

For voyeurs
Catch a burlesque show

Dixie Douya, Brandy Wine, and Busty Keaton are among the stage aliases employed by tassel-twirling dancers in Rogue Burlesque, a popular local troupe with an alternative comedy/cabaret edge. Take a striptease class with the gals to surprise your partner, or watch the pros together during their Valentine’s Day show, Swipe Right.

For puzzle geeks
Conquer an escape room

Have fun testing your teamwork at Trapology, a trendy downtown spot where you can put your heads together to decipher riddles and unlock one of six themed rooms, from a haunted submarine to the 18-plus “Boobie Trap,” available for private bookings only.

For shutterbugs
Soar high above Boston

For the most Instagram-worthy date night around, take off at sunset in one of Helicopter Tour Boston’s choppers. You and your SO will get bird’s-eye views of the glittering skyline and Harbor Islands from the comfort of the heated cab—and snap stunning photos that’ll make everyone else envious once you’re back on solid ground.

Get cuddly at Tangierino’s “Cave Table.” / Models: Victor Lopes and Kristina Dirksen / Photo by Mona Miri

Most Romantic Tables

Table 40, Parker’s Restaurant

Recapture the romance of Camelot at the very corner table where JFK proposed to Jackie Bouvier. The handsome, Brahmin-era trappings inside downtown’s historical Omni Parker House are a dignified backdrop for power couples to clink glasses and tuck into a slice of Boston cream pie, invented here.

Table 61, Deuxave

There’s an engagement every week, on average, at chef Chris Coombs’s contemporary French restaurant in the Back Bay—and most of the proposals take place in the cloistered wingback chairs surrounding this fireside table. Servers aid the surprise by delivering rings inside edible chocolate or sugar spheres.

The “Cave Table,” Tangierino

In this Charlestown Moroccan restaurant’s sultry Cave Lounge, the namesake brick table is a prime space for canoodling couples to peep burlesque performers and belly dancers. It’s also equipped with a private TV, for those who’d prefer to watch their favorite show while puffing ornate hookah pipes and noshing spicy mezze platters.

Table 24, Frenchie

Patio dining in the winter? Not advisable. But you’ll come close in the glass-enclosed conservatory of this South End bistro, which overlooks a secret garden dripping with vines. It’s a cozy spot for sipping ice cider and sharing crème brûlée—especially from the snug corner table with unobstructed views.

The “Chico Chica Boom Table,” Cuchi Cuchi

Group date? Hit this swinging Central Square spot, known for its Moulin Rouge-meets-Old Hollywood aesthetic. Up to five couples fit at a sofa-flanked table illuminated by motion-sensitive LED lights, making it a flashy, flirty spot for global small plates.

Newburyport Rear Range Lighthouse

The 360-degree views are worth the special-occasion-level splurge that secures you the single table perched inside the lantern room of this historical, 53-foot-tall North Shore lighthouse. Bring your own wine and music; the preservation society provides the staff to steward dinner from one of five neighboring restaurants.

Photo by Creative Commons/Alex Archambault (Eliza Dushku); Photo courtesy of Lamont Price; Photo courtesy of Randy Price/WCVB

VIP Valentines

Local notables share their favorite places to find romance in the city.

“Depending on the time of year, my husband, Peter Palandjian, and I like to take in a snuggly Red Sox game (likely wearing matchy sporty outfits!), walk around Beacon Hill holding hands, or grab a bite at Lone Star Taco Bar before heading to a concert or theater performance.” — Eliza Dushku, actor and producer

“Dating one woman would be unfair to all the rest, so I choose to be single. But if I plucked a lucky young lady out of obscurity, I’d go someplace cool and intimate—like Create Gallery & Cocktail Lounge at Bow Market—to relax, have a drink, and talk about important things: cartoons and snacks.” — Lamont Price, comedian

“One of my favorite romantic things to do—after a nice early dinner at a great restaurant—is take a stroll in the Public Garden. You’re surrounded by the lights and history of the city in a garden that is beautiful in the early-evening hours.” — Randy Price, WCVB news anchor

Photo illustration by Kristen Goodfriend / Photo source: Getty Images

Where to Meet Your Match

If You’re Looking for…

An animal lover
Try: Peters Park

It’s no secret that singles tend to sniff around dog parks. This South End plot, the city’s first official off-leash site, draws a notably well-groomed crowd (maybe it’s the proximity to SoWa’s new luxury condo buildings). Bonus points for the romance-themed “Cheap Date Night” menus at neighboring restaurant Myers + Chang.

A bashful bookworm
Try: Trident Booksellers and Café

Sure, you might meet-cute while browsing hardcovers in the romance section. But more likely, you’ll find a smart sapiosexual at this Back Bay indie bookstore’s near-nightly events, which range from author readings and open-mike poetry to queer board-game nights and a “self-care” series featuring adult coloring books.

A dance partner
Try: Bella Luna Restaurant & Milky Way Lounge

Attending a dance class solo is a good way to get paired with another music lover—and discover whether your hip-swaying skills are in sync. The weekly LGBTQ+ line-dancing lessons at this Jamaica Plain restaurant are a rare option for all-gender seekers and allies.

A fitness fanatic
Try: Barry’s Bootcamp

Known for its celebrity clients, famously attractive trainers, and nightclub-like music, Barry’s is less cultish than CrossFit but still draws a cliquey, self-selecting crowd of pretty people. The red studio lighting, meanwhile, casts a sexy glow on every sweaty, well-toned muscle.

A sugar daddy/mama
Try: The Red Line

Given its proximity to the New Southie real estate boom, the coffers of the Financial District, and the VC-funded tech towers of Kendall Square, this is the MBTA’s de facto love train—at least for those with a thing for upwardly mobile young professionals with bulging stock portfolios.