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26 Romantic Date Ideas In Boston That Aren’t Going To Fenway Park

Your guide to becoming the best S/O ever!
26 Romantic Date Ideas In Boston That Aren’t Going To Fenway Park

Forget Los Angeles and New York. Everybody from Boston knows that they live in the most underrated city in the states. Plus, it's never not entertaining when people try to impress you with their impression of a Boston accent. 

Even in a city where there's always something going on, it can be feel daunting when trying to choose what to do for date night. If you've been in a relationship for awhile, it gets harder and harder to surprise your partner with a new date night idea. It seems like you've done it all! And if you're in a new relationship, you always want to step up your game and impress them. 

But that's what this list is for! There are ideas for places you pass by all the time but never think to go in to, there are relaxing dates for those who want a step up from Netflix and chill, and then there are dates that revolve around food. And you can never go wrong with a date that involves eating. 

Tipsy Chocolates 

Where: Back Bay or Beacon Hill

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What pairs well with chocolate? Booze, of course! Tipsy Chocolates offers a number of tours that take you around to different shops around Boston and let you sample all the chocolate you could ever imagine. There are different ways the "tipsy" part of the tour come to play, but the best one is known as the chocolate cocktail aka the chocktail.

And if you had fun on the tour, you can also take one of their classes together and learn how to make truffles! It's a two hour class offered at the Boston Harbor Distillery. All in all, both these options are pretty sweet.


The Paint Bar

Where: 248 Newbury St

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Sure, you could get drinks at a bar and call it a night. But anybody can do that. In fact, that happens all the time. Why not see which one of you becomes Bob Ross after a couple of drinks? Register for a class at this bar and you'll receive all the tools and supplies you need to show off your artistic side. Each session takes about 2.5 hours and at the end of the night, you'll get to go home with a masterpiece! Hopefully.


Bella Santé Day Spa

Where: 38 Newbury St

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Treat. Yo. Self. Come to this spa with a view with your loved one! Book a couples massage for the two of you for the ultimate relaxation date. The treatment comes with a 50 or 80 minute option. The spa is also open until 9:00 on weekdays, so this could be an option for the two of you after a stressful day at work.


Improv Asylum

Where: 216 Hanover St

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Life's more fun when you're laughing. If you're in the mood for comedy but love the thrill of not knowing what's to come next, go and see an improv show! Impro Asylum puts on a show every single day of the week. And since it's an improv show, you never know what's going to happen. Yes, you might even be asked to come up on stage to be part of something.


Wine Riot

Where: 130 Columbus Ave

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Every year, you get the chance to try hundreds of new wines. It's a mix between a wine tasting and a convention. You can sample wines at each booth while getting to learn about what you're tasting. There are also temporary tattoo booths, a photo booth, a bubbly bar, and a big light up sign that says "Wine Riot" just waiting for you to take an Insta story in front of it. So bring along your S/O for a wine fueled night of fun.


Trapology Boston

Where: 177 Tremont St

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How well do you really know your partner? All it takes is for you two to be locked in a room for 60 minutes to complete a mission. Everybody's true colors come out when time is ticking and you're trying to solve a mystery! This is the perfect date for when you want a bit of fun and action mixed together. And if you two want to make time for your friends, bring them along too!


Judson B. Coit Observatory

Where: 725 Commonwealth Ave

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End the night underneath the stars. After dinner or drinks, head to the Coit Observatory at Boston University to observe the night sky using telescopes and binoculars. This happens every Wednesday night at 7:30 pm during fall and winter and 8:30 pm during spring and summer. Of course, it depends on the weather, but it's an amazing date if you can go on a clear night!


Boston Commons

Where: 139 Tremont St

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A park? For a date? Groundbreaking. Listen, there's so much to do in a park especially one as beautiful as Boston Commons. There are plenty of park benches for you to sit down and enjoy each other's company while the fall leaves change colors. In the winter, you can go ice skating on the pond. And in the spring and summer months, every grassy area is perfect for a picnic. Not every date has to be flashy and fancy!

Tatte Bakery and Cafe

Where: 70 Charles St

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Two coffees and cookies for here, please. This is not a place where you just grab your coffee and go. You'll want to spend forever here in this Insta perfect setting with the tiled floors and the white marble tables. They serve the most delicious cookies you'll ever taste and they go great paired with a latte. You two can grab a snack and settle in while you debate what you're going to watch on Netflix that night.


Trident Books and Cafe

Where: 338 Newbury St

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Books and all-day breakfast? Uh, yeah count us in! If you're looking for a spot to hide out from the rain or snow, this is the spot for you. It's a cozy little bookshop with all the latest releases you could ever want to read. And if you get hungry, the cafe serves everything from eggs benedict to bubble tea to burgers. The place is open from 8:00 am until midnight! This place also serves beer and wine, if you want to get really classy while discussing your book purchases.


Isabella Stewart Gardner Museum

Where: 25 Evans Way

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A quiet date filled with history and art is all you need. Museums aren't everyone's thing and that's perfectly fine! This one's a bit different though so give it a chance. First of all, the museum itself is housed in a beautiful building. The highlight of the place has to be the courtyard that's always transforming with different flowers and plants over the course of the year. Everything about it screams "I need to take several photos of this for Instagram." Go and see it for yourself!


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Boston Public Garden

Where: 4 Charles St

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This is a date worthy of being in The Notebook. Take a romantic stroll around the park just before the sun sets, walk over the foot bridge over the water, and pick a spot to sit while you watch the swans from afar. Swans are pretty, but they can be aggressive! Maybe grab a hot chocolate or hot apple cider to keep you guys warm while you spend the rest of your night here before heading home.

The Lawn On D

Where: 420 D St

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This is basically an adult playground. There's always something going on at this outdoor event space. The interactive swing display is up all the time and the swings light up at night! You can drink, play some of the lawn games, or just chill on the swings. Seriously, what more could you want for a fun night out with bae?


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Franklin Park Zoo

Where: 1 Franklin Park Rd

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Sometimes, you just want to hang out with lions and tigers. And the zoo can be a great place for a date because they often decorate the place and have amazing displays for fall and winter. If you go when it gets dark, you can catch the light up pumpkins they have everywhere! That's just a bonus when you get to hang out with sloths and red pandas for a day.



Where: 619 Tremont St

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This low key might come across as an errand, but its can be a chill date too! Come visit this beautiful garden supply store that seems like it was crafted for Instagram photos in mind. The place is overflowing with all sorts of plants and accessories all while being lit with string lights. You two can pick out some plants together to spruce up your space or just take a peek around the place.


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Fort Point Channel

Where: Congress St

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Embrace the wind! It can get really windy while you take a lazy stroll on the harbor walk, so bundle up. But it is worth it just to walk by the water and listen to the calm waves while you hold hands with your partner.

Louisburg Square

Where: Boston, MA

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If you want to be tourists in your own city, head here. Louisburg Square has brick sidewalks and cobblestone roads all lined with equisite houses. Everybody knows the real estate is ridiculous there, but you can still pretend like you live in the area! Enjoy the brisk air on a clear day and walk around while you enjoy the peace and quiet of the square.

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Where: 800 Boylston St

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Who needs the real Italy when you can have it all right here? Eataly is like having all of Italy in a marketplace. All the food in the restaurants (yes, there are more than one!) are made from scratch and a lot of the ingredients are imported from Italy. Try and get there earlier or see if you can make a reservation because it gets really busy!


Abigail's Tea Room

Where: 306 Congress St

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If you're from Boston, you gotta get tea. It only makes sense! If you choose the afternoon tea option, you'll get to sample five teas and munch on some scones, cookies, brownies, muffins, and pies. Oh, and you'll be greeted by women dressed in colonial fashion. It's really the best kind of relaxing afternoon date!


North End

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Also known as Little Italy, this neighborhood is always lively. There are plenty of cafes, pastry shops, and Italian restaurants just waiting for you. If you're looking for a more active kind of date, the heart of the Freedom Trail is in the North End neigborhood, so go ahead and take a nice walk!

Beacon Hill

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Home to the famous Acorn St, Beacon Hill has so much going for it. Take your partner here when you want to do some shopping without heading to a big mall where you're constantly around huge crowds of people. Beacon Hill has all types of unique boutique shops that are fun to just go in and take a look.

Institute of Contemporary Art

Where: 25 Harbor Shore Drive

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There's art for you to see, but there's also a great view of Boston from inside! The museum is also free every Thursday night from 5-9, if you're looking for a fun date that costs nothing. The museum always has rotating exhibitions, so you're guaranteed to see something new each visit. And if you go during an event, well, you're in for a treat. There's live music, food, performance art, and more!


Rose Fitzgerald Kennedy Greenway

Where: 185 Kneeland St

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Parks, parks, parks. They don't all look the same! This one has bench swings, a carousel, foutains, and a labyrinth that's not just for kids. It's actually really fun to go down the circular winding path in the lawn. Escape here for a couple hours to get away from the stress of life with your loved one. Sometimes, all it takes is good company and a good swing to end your day on a happy note.

Spectacle Island

Where: Boston Harbour

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Take the ferry for a fun adventure! Just 20 minutes from Boston Harbor is an island where you can see the amazing skyline of Boston. You could easily spend the whole day there walking, having a picnic, and relaxing by the water.


Top of the Hub

Where: 800 Boylston St

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This is where the magic happens. Well, this is certainly where fancy lives. You can take bae here for drinks or for dinner as you look over at Boston from 52 floors above Black Bay. Everything is on the pricier side here, so this could be the place for celebrating special moments in your relationship or for celebrating an anniversary.


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Shear Madness

Where: 74 Warrenton St

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Murder, comedy, and a hair salon? These are the ingredients for a laugh-out-loud date night when you come see the Shear Madness show. The show changes every single night because there's audience participation and improv involved! So spend the night trying to catch a killer and you might even be in on the hunt too.


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