Romantic Things to Do in Boston

From gondola rides to the 'Long Path,' here are romantic activities around Boston you and your partner can enjoy all year round.

bpl courtyard

The courtyard at the BPL. / Photo by Olga Khvan

Sure, the pressure’s on to be romantic on Valentine’s Day, but what about the other 364 days of the year? Here are some starter ideas, from casual walks through the park, to fancier fare you’ll need to schedule in advance.

The Long Path in Boston Common

Is the Public Garden more picturesque with its footbridge and swan boats? You betcha. But the Common’s Long Path, which runs straight from the southeast corner at Boylston and Tremont Streets all the way up to Joy at Beacon Streets, has quite a romantic story behind it: In Oliver Wendell Holmes’s Autocrat of the Breakfast Table, the autocrat proposes to his beloved here by asking if she will take the Long Path with him, i.e. the path of life.

More romantic routes: the Commonwealth Avenue Mall, the trellis at Christopher Columbus Park, Harvard’s Arnold Arboretum.

A Night at the Theater

While actual opera may or may not be of interest to you, any ballet performance, orchestral show, or musical at the Boston Opera House, Symphony Hall, or other classical theater in town is a great excuse to dress up a bit. The fancy attire and upscale venues alone will enact a Pygmalion effect on you and your date. If you really want to go all out, spring for box seats.

If you would like an intro to opera: Opera on TapOpera Night at the BPL.

Urban Oases

In our digital age, there are many reasons to not leave the house anymore. Why go to the movies when you have Netflix? But the museum remains a venue to be reckoned with. The environments are designed to be peaceful, inviting, and above all, beautiful. Hence, the ideal romantic venue. Lucky for us, there are plenty such spaces in Boston. A few of our favorites:

• The tropical courtyard in the Isabella Stewart Gardner Museum. Visit during special event series like Third Thursdays, Stir, or the Sunday Concert Series for an extra dose of entertainment.

• The Impressionist Gallery at the MFA. The newly renovated room featuring Monets, Renoirs, and more is full of romance. Don’t believe me? Take it from this guy, who proposed to his fiancée there last fall.

• The Poss Family Mediatheque at the ICA. Despite boasting sweeping views of the Harbor, it’s the museum’s Mediatheque where you’ll be least disturbed, with a window that faces downward toward the water.

Another spot with a supreme, serene courtyard: the Boston Public Library.

All That Jazz

OK. Maybe you are unable to serenade your sweetheart. No problem. Let the folks at Scullers Jazz Club provide the soundtrack to a fun night out. Tucked away at the Doubletree Suites in Allston, Scullers has a history of attracting big names in the jazz scene, from Tony Bennett to Harry Connick Jr. It’s up to you whether or not to take advantage of their dinner and overnight packages.

Other jazz spots: Wally’s, The Beehive, Ryles, Regattabar at the Charles Hotel.


An evening under the stars? Sounds like a prom theme. But in reality, there are only so many places to gaze into space unless you have your own telescope at home. Now, Astronomy After Hours at the Museum of Science is open to families too, but don’t let the kids’ “Oohs” and “Aahs” distract you from the romance. In fact, join them. When it comes to space, we are all children. (Every Friday, weather permitting, call ahead.)

Also offering free observatory nights (again, weather permitting, call ahead): BU (every Wednesday), Harvard (every third Thursday).

Outdoor Ice Skating

A lot of people recommend ice skating at the Frog Pond, and considering it’s on the Common, that’s certainly the obvious choice. But unless you consider dodging dozens of wild children—and their frantic parents—romantic, you might want to try a rink that’s slightly less centrally located. Community Ice Skating at Kendall Square is a spacious rink, and the Charles Hotel, also in Cambridge, has a nice smooth sheet of ice as well. In the city, consider Boston Harbor Hotel’s rink, which is small but oh-so-pretty underneath the hotel’s signature arch on the Waterfront.

Boston Common Frog Pond, Boston Harbor Hotel, Charles HotelCommunity Ice Skating at Kendall Square.

Gondola Rides

An indoor gondola ride at the Venetian in Vegas? Cheeeeese. But did you know you and your significant other can take a gondola tour on the Charles? Gondola di Venezia offers three different gondola tour packages, which take passengers on romantic trips off the Esplanade. They’re a bit pricy, but considering the amenities—roses, champagne, cheese and crackers, chocolate, and more—a gondola tour is a worthy splurge for a special occasion.

Picnic with a View

Delicious food, fresh air, and a killer view makes for one fine picnic date. When the weather’s nice, pack a basket—or pick up a professionally prepared one—and head to the hills. Corey Hill Outlook has a great view of the city from afar, as does Dorchester Heights, just to name a few. But of course, any spot by the water—Piers Park in Eastie, for example—would also be nice.

Hidden gem: Cambridge Center Roof Garden.