Looking for fun date ideas in Boston? Whether you’re planning your first date or 50th date, Boston has an abundance of activities for couples. Here are 11 unique things for couples to do in Boston, from kayaking the Charles River to painting classes.
Guest Post by Sacha from Sacha Eats
Date Night Ideas In Boston
Challenge Your Partner to Some Board Games
Play some board games and sip on a coffee at Knight Moves Cafe, one of the only board game cafes in the Boston area. It’s $10 per person on weekdays and $15 on weekends for unlimited game play. With over two thousand board games in their collection, you’re bound to find a game you love or discover a new one!
As you play, you can purchase coffee and pastries from their refreshments menu. They also allow you to BYOB, but you’ll need to pay an extra charge.
Discover a Boston Speakeasy
One of the coolest speakeasies is Offsuit in the Leather District. It’s located in an alleyway and you need to call the number at the door in order to be let in. The inside is intimate and dimly lit, with rustic decorations and plush sofas.
Another cool speakeasy is Next Door in East Boston. Check-in at the restaurant Pazza on Porter.
They’ll give you a password and direct you to the speakeasy. Once you arrive at the entrance, make sure to tell them the password to be let in!
Next Door is well-known for their creative cocktail presentations. Some drinks are lit on fire while others come in a treasure chest.
It’s also a raw bar, so you can get a variety of seafood tapas including ahi tuna tacos, tuna crudo, and ceviche.
Paint & Sip at Muse PaintBar
Tap into your creative side at Muse PaintBar in Somerville’s Assembly Square.
Muse is a combination of a bar and painting class. You first reserve your class spot online from a wide selection of painting options.
When you arrive at the class, they’ll already have your canvas, apron, and supplies set up. Then it’s time to paint!
The class is instructed by a local artist, who thoroughly guides you through each step.
It’s open and accepting for all experience levels, so don’t feel hesitant if art isn’t your forte.
There’s also a bar menu to get your creative juices flowing and a food menu in case you get hungry.
It’s a fun, stress-free date idea in Boston. Best of all, you get to bring your new art piece home!
Attend a Sports Game
Boston is a HUGE sports city and is home to many amazing sports teams with a strong fanbase.
I recommend seeing a Red Sox game at Fenway Park. The atmosphere of each game is electric and fun!
While you watch the game, enjoy a beer and Fenway Frank hot dog. The Fenway Frank is a Boston staple; it’s a hot dog that’s been boiled and grilled.
During the off-season, you can take a guided Fenway Park walking tour to learn more about the history of the stadium.
Built in 1912, Fenway Park is the oldest MLB baseball stadium that’s still in use. It’s also the third smallest stadium in the league!
Not into baseball? The TD Garden arena hosts Celtics and Bruins games for basketball and hockey fans.
See a Broadway Show
Next on the list of Boston date ideas is a night out in Boston’s Theater District. First, grab dinner at Mooo, one of Boston’s best steakhouses. The restaurant is known for its sophisticated atmosphere, high-end cuts, and award-winning wine selection.
After dinner, walk over to the Citizens Bank Opera House for a Broadway show.
Depending on the season, you can see a ballet or musical. One of the most famous ballets hosted here is the Nutcracker during the holidays. Musicals that have toured here include Hamilton, Wicked, & The Lion King.
Not only are the performances incredible to watch, but the interior of the opera house is beautiful! The historic theater is elegantly decorated with gold hues, marble columns, and chandeliers.
Have a Picnic on the Esplanade
The Charles River Esplanade is one of Boston’s biggest parks. It extends for three miles, starting from Beacon Hill and ending at the edge of Newton.
The paths are well-suited for jogging, biking, hammocking, and rollerblading. There’s also a playground and outdoor calisthenics gym.
For some quick and easy picnic food, grab a charcuterie box from Kured in the Beacon Hill neighborhood.
Their takeout charcuterie boards are fully customizable. You can choose from a variety of cured meats, cheeses, nuts, and other toppings. It takes the stress out of buying ingredients in bulk.
The best place to set up your picnic is on the docks on the Esplanade. Since it’s on the water, you’ll get a full view of Cambridge across the river.
Explore & Eat at the Isabella Stewart Gardner Museum
The Isabella Stewart Gardner Museum is a must-see museum in Boston, even if you’re not into art.
First off, the courtyard in the center of the museum is breathtaking. Its vibrant greenery, statues, and old-style architecture make it the perfect spot to take pictures!
The museum has eclectic artwork split into themed exhibits. As you walk through each, you have the option to listen to an audio guide to understand the museum better.
It’s famous for a heist in 1990, where 13 pieces of artwork were stolen. Those art pieces are still missing and they have yet to find the culprit.
After some sight-seeing, have a bite inside the museum’s cafe. Cafe G is located on the front podium of the museum and has both indoor and outdoor seating.
The menu includes your typical cafe fare like sandwiches, pasta, and salads. The cafe has a relaxed ambiance and is the perfect place for people to watch.
The entry fee to the museum for adults is $20, but if your name is Isabella you can enter for free! Just bring a valid ID.
Hike the Blue Hills
Get into nature by taking a 30-minute drive from Boston to the Blue Hills Reservation in Milton, Massachusetts.
There are a variety of hiking trails to choose for all experience levels. For a leisurely stroll, do the Ponkapoag Pond Trail loop.
It’s a flat trail that extends 6.8 miles and takes about 2 hours to complete. Popular activities along this trail include fishing, camping, and birding.
For a more challenging hike, I recommend the Great Blue Hill Skyline Trail.
The 1.5 mile path takes around 2 hours round trip to complete and is marked by a blue line on the ground. Some sections of the hike get steep, so make sure to wear proper hiking shoes.
Once you reach the end of the hike, climb the watchtower to see a skyline view of Boston.
Seasonal Things For Couples To Do in Boston
Go Apple Picking
In the autumn, go apple picking while enjoying the New England fall foliage at one of the many nearby farms.
Honey Pot Hill Orchards in Stow, Massachusetts is the perfect spot to go apple picking. There are lots of apple variations to choose from and you pay by the pound of the bag.
There’s also a hay ride and a store with seasonal produce including apple cider, caramel apples, pumpkin pies, and more. Make sure to try the Honey Pot Orchards apple cider donuts.
The cake-like donuts are made to order and have an apple-cinnamon flavor. Enjoy the donuts with apple cider at one of the picnic tables on the farm.
Ice Skate at the Frog Pond
A fun winter date idea in Boston is ice skating at the Frog Pond! The outdoor rink is located at the Boston Common, right in the heart of Downtown Boston. It has a relaxed atmosphere and skaters of all experience levels.
You can buy tickets either online or at the rink. They have ice skates rentals, as well.
Keep in mind that the rink gets very busy on weekends, so I recommend going on a weekday or right when it opens.
Cruise the Charles River
A perfect outdoor activity in the summer is paddling down the Charles River. Kayak and stand-up paddle board rentals are available at Community Boating.
The dock is located at Charles/MGH station and you’ll be boating between the Massachusetts Ave bridge and Longfellow bridge. It only costs about $34 per person for two hours.
Since the Charles River splits Boston and Cambridge, you’ll have the perfect view of both of their skylines as you cruise down!
Boating is open from April to October, but it’s best to go between June and September to enjoy the warmer weather.
An alternative rental company is Paddle Boston, which has docks in Medford, Boston, Cambridge, Newton, Somerville, and Waltham.
Wrapping Up: Date Ideas in Boston
Now that you’ve read through 11 unique date ideas in Boston, it’s time to go out and experience them with your special someone!
Author Bio: Sacha runs the Boston-based travel blog Sacha Eats. As a life-long Bostonian who’s explored 400+ spots, she covers the city’s best food and things to do.
Sara, a seasoned expert in wedding planning and date ideas, brings a wealth of experience to our couples blog. With a background in the television industry and hands-on involvement in a dozen weddings, including working as a wedding assistant on "My Fair Wedding with David Tutera," Sara has an innate understanding of the magic that makes weddings truly special. Growing up with four sisters has given her unique insights into the dating world, making her a go-to source for practical and heartfelt dating advice. Her knowledge and enthusiasm make her the perfect guide for couples seeking to infuse their relationships with creativity and love.