13 Best Original Date Ideas in Boston (2024)

Chloe MullinerChloe Mulliner
Chloe Mulliner
6 min read
Published in Date Night 


    In a rut when it comes to brainstorming date ideas in Boston? Check out our list of the best indoor and outdoor date ideas in Boston for inspiration.

    Boston, Massachusetts, has a lot going for it, but it’s easy to get bored if you’re frequenting the same date spots day in and day out. However, the beauty of this city is that there is always something new and exciting to experience—it’s just a matter of knowing where to look!

    In our guide below, we’ve rounded up 13 of our favorite date ideas in Boston, from setting sail around the harbor to rock climbing at an indoor gym. Whether you’re getting back out there and going on a lot of first dates or having trouble coming up with new spots to take your partner, refer to our list when planning your next date night in Boston.

    1. Play Tourist for the Day

    We often try so hard to avoid looking touristy while in the city, but there’s a reason why tourist attractions gain so much attention—they can be a lot of fun! For this Boston date idea, give yourselves permission to be tourists for the day and do all the iconic Boston things. Yes, that means walking the Freedom Trail, exploring Harvard Square, and of course, topping it all off with a bowl of clam chowder and a slice of Boston creme pie. And if you really want to go all out, get tickets for the hop-on, hop-off Old Town Trolley Tour, so you can cover more ground. 

    1. Wine and Dine in the North End

    You don’t need to jump on a flight to Europe to indulge in Italian cuisine. Plan a date in North End, aka Boston’s Little Italy, which is celebrated for its American-Italian influences. It’s in this part of town where you can dine on some of the most delectable Italian cuisines, from cannolis and calzones to pizza and gnocchi. Make reservations for a romantic dinner for two and spend your evening sipping wine and dining on authentic Italian fare. 

    1. Take Them Out to the Ball Game

    If you’re looking for an outdoor date idea in Boston, look no further than Fenway Park. Of course, this iconic stadium is home to the Boston Red Sox. Get tickets and root for the home team as you nosh on Fenway Franks and Grillo’s Pickles. You and your date certainly don’t have to be sports fanatics to enjoy a day at the ballpark cheering on Boston’s finest. 

    1. Get Artsy

    If you both live in Boston, chances are, you’ve already been to the Museum of Fine Arts a time or two. But that’s certainly not the only place you can marvel at masterpieces in town! For this Boston date idea, tap into your artsy sides and visit the Isabella Stewart Gardner Museum. In addition to the art pieces, the museum itself is a work of art, from its stunning architecture down to its immaculate gardens. Spend your date marveling at this institution, and be sure to learn more about the infamous 1990 art heist that still remains unsolved today.  

    1. Slip into a Speakeasy

    Boston is home to countless dive bars, but if you really want to make a good first impression, invite your date to one of the local speakeasies. A nod to the underground operations during Prohibition, these trendy bars give off a mysterious flair while serving up thoughtful, handcrafted cocktails. Search for the hidden entrance to Hecate, a bewitching bar named after the Greek goddess of magic and witchcraft, or find your way into Next Door, where you can sip on specialty cocktails and caviar. 

    1. Hit the Trails

    Hiking Middlesex Fells Reservation is easily one of our favorite summer date ideas in Boston. This nature spot is ideal for outdoorsy couples, as you can spend the day kayaking on Spot Pond, casting a line for some fish, and hiking the many trails. But if you really want to make this a memorable date, head to the park at the golden hour, pack a picnic and blanket, and cozy up together as you watch the sun fade over the sparkling city skyline. 

    1. Slur Oysters

    New England is known the world over for its oyster beds, so you better believe Boston serves up some of the freshest oysters in town. If you and your date like seafood, then make your way to one of the city’s many raw bars, from Row 34 to Neptune Oyster, to slurp down some cocktails and oysters. And you know what they say; oysters are said to be aphrodisiacs! 

    1. Set Tail Together

    Why plan a date night in Boston on land when you could arrange one on the water? For this ultra-romantic idea, charter a private sailboat and enjoy a fun-filled day (or evening) cruising around the harbor. You and your date will have a grand time sailing around the islands, seeing the city from a different perspective, and learning about the local history along the way. Some charters even allow you to bring your own food and beverages aboard. Just be warned, this is one date that will be hard to top!

    1. Get Adventurous

    If you’re an adventurous duo, then bring your relationship to new heights at one of the rock climbing gyms in town. This date idea in Boston is ideal for couples that aren’t afraid of a little challenge as you tackle the bouldering caves and scramble up the rock walls. Between Central Rock Gym, Boston Rock Gym, Rock Spot Climbing, and others, you’re sure to find an indoor crag that suits your fancy!

    1. Skate Figure 8s

    What can couples do in Boston come wintertime? Ice skating! During the winter months, the Boston Common Frog Pond transforms into a winter wonderland, where you and your date can take a spin around the frozen pond while holding hands in the frosty air. Afterward, head over to the Frog Pond Cafe and warm up with some hot chocolate. 

    1. Plan a “Fancy Night”

    Just because you’re planning a date doesn’t mean you have to go out on the town. In fact, one of our favorite at-home date nights involves getting dressed to the nines and ordering from a top-rated restaurant like Cafe Sushi for Japanese food, Mida for Italian, or Craigie on Main for some French-inspired cuisine. The beauty of this idea is that you can both get dolled up and enjoy a delicious meal from the comfort of your own home, which means you can mix your own cocktails and DJ your own playlist. 

    1. Catch a Show

    The Wang Theatre at the Boch Center has long been celebrated for its brilliant shows and productions. Built in 1925, the theater has become a staple for the city’s finest performances, from musical acts and dance numbers to comedy shows and lectures. Before attending a show, explore Boston’s Theater District with your date and grab a bite to eat. In fact, many restaurants in the district, such as Maggiano’s, Montien Thai Restaurant, and Bistro Du Midi offer dining discounts when you present your theater tickets for a same-day performance. 

    1. Skip the Dinner and Movie Idea

    If you’re dating an independent woman, the ol’ dinner and a movie date might not cut it when it comes to date night in Boston. Instead, think outside of the box and get a little creative. For example, you could venture to the Cantab Lounge, which hosts a Boston Poetry Slam every Wednesday, or spend the evening listening to some sultry live music at Scullers Jazz Club. From tracking down the city’s stunning murals to attending a pottery class together, you’ll find so many alluring (and romantic!) things to do in this city that will surely leave a lasting impression. 

    From getting in a little workout together to exploring new parts of this city, these Boston-centric ideas are not only great for those wanting to plan successful first dates, but also for those looking to keep the romance alive in their current relationships. 

    Get Started Toward Your Last First Date

    Try Tawkify today. We only accept candidates we believe we can match.