When drinks and dinner don’t cut it anymore, why not switch things up? Whether its your first date or 50th, its time to break free from your monotonous date routine. From swing sets and swan boats to kayaking and cannoli, here are 15 Boston date ideas to give you and your loved one a jumpstart on exploring the one and only Beantown.
Boston’s newest interactive outdoor space is the perfect place to peruse with your person. Take a picnic in the parkway, play lawn games like ping-pong and bocce, and have a photo-op in their iconic swing set (be sure to come back at night for a totally different atmosphere). The Lawn on D is also a great excuse to explore the newly renovated Seaport District of the city. Check their calendar for Seaport events coming to the Lawn.
A visit to Boston’s historic North End isn’t complete without stepping into Mike’s Pastry. Since 1946, Mike and the entire Mercogliano family have been concocting their famous cannoli recipe, which has become a cherished staple of the North End (the Little Italy of Boston). Treat your sweet one to this delightful dessert, Lady & The Tramp style.
For independent cinema lovers, the Coolidge Corner Theatre is New England’s “most successful independent, nonprofit cinema,” boasting classic vintage titles, new independent cinema, and the occasional mainstream hit, all housed in its Art Deco-style movie palace. Its annual “Coolidge Award” highlights one prolific actor each year, whose titles are showcased and, if you’re lucky, may even make a guest appearance.
There is no better way to spend a summer afternoon than taking a Swan Boat out for a spin in the Boston Public Gardens (the first public botanical garden in the country, and one of the most romantic). These picturesque pontoon pleasure boats can accommodate a cozy couple, or the whole family, and will gently sway you through the beauty of this Central Boston green space; all you have to do is sit back and enjoy the view.
You can’t talk about Boston without talking about the Red Sox and Fenway Park. Whether you’re a baseballer or a benchwarmer, catching a home game at the renowned stadium is a quintessential Boston date idea. Enjoy a classic Fenway Frank while rooting for the home team, sing along to Sweet Caroline, and keep a lookout for your cameo on the Kiss Cam.
A fan favorite venue for up-and-coming musical acts, as well as heavy hitters alike, The House of Blues Boston is the chicest spot in the Fenway neighborhood to mix, mingle, and mosh out to your favorite artists coming to town, staying true to their motto “Unity in Diversity.” Be sure to take your date over to their nightclub Restaurant & Bar before the show, but don’t miss the opening act!
Spot each other as you tackle Brooklyn Boulders’ indoor climbing walls that stretch up to 50ft high, with challenges and classes for any and every skill level. Once you’ve worked up a solid sweat, head next door to Aeronaut Brewing Company and relax with a tall pint and enjoy one of their many events including live music, workshops, and trivia nights.
Housing European, Asian, and American art in Isabella’s beautifully designed former home, the Isabella Stewart Gardner Museum is curated with paintings, sculptures, tapestries and decorative arts to feel like a calm lover’s stroll through one’s own home, all centered around the grand indoor atrium fitted with exotic greenery. Learn about the museum’s infamous art heist of the 1990s, and get in free if your name is Isabella!
Sip on some of the freshest local coffee beans that Beantown has to offer (and their hand-crafted bagels aren’t bad either). This new-age, small and local chain has its cute cafes scattered throughout Boston and Cambridge. Pavement Coffee is perfect locale for a first date or hundredth, and their roastery is even located just off of the banks of the Charles River.
What better way to explore the city than a leisurely kayak adventure for two? You can ride the river through as many as 23 cities before reaching the beautiful Boston Esplanade parkway. With Paddle Boston, you and your date can choose your start and end locations, and take in Boston’s famous skyline including college campus sights like MIT, Boston University, and Harvard.
The cobblestone streets of the famous Faneuil Hall are beaming with history, as well as with food. This historic meeting place for Bostonian patriots is now a metropolitan food and shopping market where you and your date one can indulge in some of Boston’s new and old delectables, including Boston Cream Pie, Boston Baked Beans, and New England Clam Chowder. Enjoy your treats while you take in the many street performers that occupy the courtyards.
For those betrothed bookworms, the Boston Public Library is an endless source of enjoyment. As the 3rd largest library in the nation, this massive marvel of literature, art, and architecture houses over 23 million items, and is also the pioneer in many facets to the modern-day library services that developed throughout the country. The library makes for a perfect, unique date idea if you’re looking to spend a rainy day losing track of time and soaking up as many great writers as you can.
Famously the most photogenic street in Boston, this blast-from-the-past backdrop in the alcoves of Boston’s elite Beacon Hill neighborhood ignites the nostalgia of the colonial Bostonian era, lined with cobblestones, colonial light fixtures, and Georgian brownstone homes. Acorn Street is an especially romantic rendezvous when it is freshly lined with autumn leaves or spring petals. Keep in mind this is still a residential street, so couples need to share the space with locals and other photo-oppers (it can get crowded at peak times).
Visit the bar that helped put Ben Affleck and Matt Damon on the road to global film fame for its appearance in the Academy Award winning film, Good Will Hunting, portraying the boys’ local hangout spot in the movie, and located in their real-life hometown of South Boston, or “Southie,” as the locals say. Offering hearty brews and a hometown Southie spirit, L Street Tavern is your classic old Irish pub that is bound to bring some warmth to your Boston date night.
Located in Cambridge, Boston’s neighboring sister city, Harvard University is the oldest university in the United States, and is one of the most prestigious schools in the world. Harvard Yard holds many of the school’s important buildings and libraries, and mosying through the grounds is a lovely way to take in the culture of the university. And when you’re finished studying the Yard, step outside the gates to the cultural hustle and bustle of Harvard Square–lovingly referred to as “The Square”–a bohemian triangular plaza filled with food, shopping, and music for everyone to enjoy (no PhD required).