02/10/2022

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10 Fantastic Boston date ideas you will love

10 Fantastic Boston date ideas you will love

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From romantic picnics under the willow trees to Boston date ideas for the sporty couples (baseball, anyone?). Boston in Massachusetts, USA, is a treasure trove of things to do for couples.

There’s something enchanting about the cobblestone, the brick sidewalks, the lanterns, and the thriving foodie and culture scene in Boston. Going on a date in Boston is never a boring thing.

10 Fantastic Boston date ideas you will love
Look at this view. Boston is a romantic city!

With a young population of college students and young professionals, there’s never a lack of events, galleries, new exhibits, or places to feel the Boston energy with your date.  

Whether you’re looking for something on the quieter side so you can get to know each other more or are searching out where to take a date in Boston with an electric vibe to bring out both of your personalities, this is the list for you!

We cover everything, from first date ideas to things to do in Boston for couples. And at the end of this romantic guide, you will find four hotel suggestions. They are the perfect match for these amazing date ideas. 

Boston date ideas for all types of couples

Photo of Boston Common park during autumn. The trees are becoming yellow, creating a perfect scenario for a picnic, and it's the first Boston date idea of this guide.
Boston Common is lovers’ favorite place in the warmer season.

1 – Have a romantic picnic on Boston Common

Boston Common is a large green space in the center of the city, in the Beacon Hill area, surrounded by beautiful buildings. It is a perfect place in Boston for a date when you want some room to yourselves and some quiet time together.

While it is a public park bustling with people playing games, sitting by the water, or walking and talking, you’ll easily be able to find your own ideal spot to enjoy yourselves.

In the warmer months, take a picnic blanket and spread it out on the grass. Pack your favorite sandwiches and desserts, along with something to toast with, and use the time to learn more about each other.

You can spend the whole afternoon there until the night sky shows. Then you can go to a bar or restaurant for a romantic night out.

Bonus: this is definitely one of the cheapest date ideas in Boston. Perfect if you’re both students or just need to save a little bit of cash while still having a good time. 

Photo of Tatte cafe facade in Boston city. It's a great place to take a date in Boston for coffee and pie.
Boston date spot for coffee lovers!

2 – Get coffee and cake at Tatte

Boston is filled with cafes, but none as good as Tatte. There are a few locations dotted around the city, but no matter which you choose, you’ll enjoy the light and airy atmosphere and the fantastic array of food options. 

They are great at catering to special dietary needs, which can be helpful if you don’t know your date that well yet, and the pies are out-of-this-world good. This might not be the most romantic restaurant in Boston, but it certainly is a great place for a first date and for coffee lovers. 

Collage of a photo of Omni Parker House hotel lobby with a picture of the famous Boston Crème Pie created at this hotel in 1855. It is a fun idea for an afternoon or night date idea in Boston.
Food is an aphrodisiac!

3 – Get Boston Crème Pies at the Omni Parker House

All dressed up and need somewhere to go? Experience the best of Boston while enjoying Boston Crème Pies at the Omni Parker House, the original location where the Boston Crème Pie got started!

You can grab your pies and eat them in the gorgeous lobby of the hotel, people-watching and seeing what all of the fuss is about (spoiler alert: they’re amazing). It’s truly a sweet, delicious, and romantic experience. 

Photo of Boston Bruins hockey game at TD Garden. This is a good date idea for sports fans or couples who love hockey.
Calling all hockey fans out there!

4 – Cheer on the Boston Bruins at TD Garden

Looking for awesome date ideas in Boston for sporty people? If you love a fun atmosphere and cheering for the local team, a Boston Bruins game at TD Garden is for you.

Bostonians love hockey, and there’s no better place to see it than the TD Garden.

Get some food at the concessions stand and a foam finger for good luck, and spend the evening cheering, clapping, and supporting Boston. 

Even if they lose, fans are with the team through and through, and they’ve even been known to chant “we still love you!” after a particularly hard fought game. That’s true love!

The vibe is fun, friendly, and perfect for letting loose a bit and having a different kind of date night in Boston.

The Freedom Trail is one of Boston's tourist attractions that can be fun for couples.
What about a holding hands walk?

5 – Walk and talk along the Freedom Trail

While the Freedom Trail is known for being a great place for tourists to explore Boston’s attractions, it’s also a fantastic option for those looking for active date ideas in Boston.

Because the trail itself is quite literally marked in the road, you and your date can walk the whole Freedom Trail without needing to spend time looking up directions or wondering where you’re going.

Just start at the beginning, in Boston Common, and walk the 2.5 mile trail, people-watching and getting to know each other better along the way.

Some people also feel more comfortable opening up when they’re involved in another fun activity or not sitting at a table across from each other. So going for a walk with things to see along the way can help you take your relationship to the next level while not putting too much pressure to always have something to say! Definitely a great idea for romantic things to do in Boston that don’t need much effort. 

If you want to be a tourist in the city or impress your date with some historical information about Boston, you join a guided tour. This 2.5 Hours Walking Tour of the Freedom Trail runs morning and afternoon and has great reviews.

Photo of the interior of Quincy Market with people queening in front of the food stalls. It's a fantastic place to go for a lunch date in Boston. Many options for food.
Who doesn’t love a food market date?!

6 – Visit Quincy Market

Quincy Market, arguably one of the most iconic food markets in the entire nation, is a fantastic place for a lunch date in Boston.

There are so many options, ranging from Italian to seafood to all-American burgers, as well as dessert stalls. Each of you can get exactly what you want and then sit down in one of the large seating areas to enjoy.

This is a great idea if you both work in Boston and need somewhere to meet during the day or if you’re not incredibly familiar with the city as it’s really hard to miss. After the date, stroll around the area to admire the great views from Boston Harbor while holding hands. 

Photo of the Fenway Park facade with a big sign of the Red Sox baseball time on top of the wall.
Sporty couples will have fun in Boston!

7 – Take a tour of Fenway Park

Need a Boston date idea for a baseball fan? There’s nothing better than a Red Sox game, but what about taking a behind-the-scenes tour of Fenway Park?

The tour will take you into all of the areas regular fans can’t access, as well as give you a history of the park that any baseball fan will enjoy. 

It’s something a bit different, perfect if you are looking for fun date ideas in Boston. And even if you aren’t huge baseball fans, the enthusiasm of the guides and their love for the Red Sox will blow you away.

Photo of the e iconic Goodwill Hunting bench located at Boston Public Garden.
Fan of movies? Here is a date idea for you!

8 – Find the iconic Goodwill Hunting bench

Impress your movie-lover date by taking them to the iconic Goodwill Hunting bench.

This bench, known from the park scene in Goodwill Hunting where Robin William’s character delivers his famous monologue, can be found in Boston Public Garden.

There’s no plaque or mention of it within the park, however, if you start at the western end of the bridge and walk north, it will be the third one you’ll come across. Check the bench, and stroll around the garden. It’s one of the perfect things to do in Boston as a couple, especially if you both like movies.

Photo of the o Ye Olde Union Oyster House facade, the oldest restaurant in Boston that also serves up some of the best seafood in the city.
Boston date ideas for (seafood) lovers!

9 – Enjoy clam chowder at Boston’s oldest restaurant

Want to have a different and nice dinner date in Boston? Take them to Ye Olde Union Oyster House, the oldest restaurant in Boston that also serves up some of the best seafood around.

When you’re in the northeast, you’ve got to try the clam chowder, but you can also dig into some sautéed scallops, fish chowder, lobster rolls and more.

If you aren’t sure if your date is a seafood eater, they also do salads, steak, chicken, and some other delicious food options so you can enjoy the historic setting regardless. 

A dinner out is one of the easiest date night ideas, and you can always stretch to a bar, a comedy show, a theater, or a club. Boston has plenty of options for a night of fun.

Path walk along the Charles River in Boston. A great place for dates in Summer and during the winter in Boston.
Boston city views and Autumn colors to fill up your eyes and hearts!

10 – Wander along the Charles River

Boston developed around the Charles River, a vast waterway that cuts through the city and provides gorgeous views on both sides.

For the best views of Boston, though, we like to walk along the Charles River on the MIT side. This is the perfect spot to see the Boston Skyline in all of its glory.

Join hands and take your time as you meander down the tree-lined walkway and appreciate the beauty of your date and this iconic American city skyline. 

We’ve listed 10 ideas for romantic dates in Boston, now it’s up to you to choose or favorite or maybe try all the date spots. Boston is a surprising city with plenty of things to do and see.

However, we still have one more recommendation to share with you. We can’t talk about things for couples to do in Boston without talking about romantic hotels. You might want to end your date night in Boston in a nice hotel or do a weekend staycation with your loved one. So here they are: 

The most romantic hotels in Boston

Unique dates deserve lovely stays. It doesn’t matter your style of dating, there are hotels in Boston that can fit perfectly with your romantic mood. We choose 4 romantic hotels in Boston that are very different from each other and will give you extraordinary comfort and love vibes.

Mandarin Oriental Boston Hotel

This is the perfect hotel for couples who want to relax and indulge in some luxurious spa sessions. Look after your body, mind, soul, and soulmate at the only Forbes five-star awarded spa in Massachusetts. The hotel also has restaurants and bar on-site and comfy rooms.

The Mandarin Oriental is the perfect match for a pampering stay, one of the most romantic hotels in Boston. Plus, it has a great location near Commonwealth Avenue, a linear park with historical buildings and statues, and a few steps from Newbury Street, a shopping street.


W Boston Hotel

Location, modern and comfy rooms, and a good bar, the W Boston Hotel has everything a couple might need for a night, or weekend, of fun in the city. 

The property is only 5 minutes walking from Boston Common – perfect to combine with the picnic date idea. It has that party vibe going on with music, events happening on the weekend, and a busy bar. But if you want to let your hair down, you can relax at the hotel spa. 


Boston Hotel Commonwealth

If you guys like sports, this is the best place to stay in Boston. And if you are a fan of baseball, then this hotel might be one of the most romantic places in Boston for you. Do you want to know why?

Boston Hotel Commonwealth rooms have views of Fenway Park. Yes, you can wake up with views of this iconic landmark in Boston, perfect for those who want to watch a game and be close to the venue.

It’s also close to other interesting places to visit in Boston with a date, such as the James P. Kelleher Rose Garden, Isabella Stewart Gardner Museum, Boston Museum of Fine Arts, MassArt Museum, many bars, and concerts venues.

Apart from the location and its views, the hotel also has an on-site restaurant and even an oyster bar. I told you it was a romantic place to stay!


Moxy Boston Downtown

Here is an affordable hotel option for a romantic stay in Boston because not all dates need to be luxurious and expensive, right?!

Moxy is located in Boston city center, close to Freedom Trail (one of our recommended romantic spots), and it’s easy to get around and enjoy the city’s nightlife. It’s a 4-star hotel offering rooms with great views, good value for money, and a party-loving atmosphere. It sounds like a fun experience, right?!

If you are not sure where to stay in Boston for a romantic getaway, then keep searching on Booking.com. You can also find tips about booking the perfect hotel anywhere in the world in our Accommodation Guide.

Now we covered everything, from date ideas to lovely hotels and romantic things to do in Boston. Which suggestion is your favorite? We hope this guide inspires you to plan a day trip with your date or maybe a romantic trip to Boston, but above all, that it inspires you to celebrate love!

Love this Boston date ideas guide? Pin it for later!

The best Boston date ideas for all types of couples! We covered everything from cheap date ideas in Boston to things to do as a couple and romantic hotels.There are also Boston date night ideas, suggestions for sporty couples, first-time dates, romantic restaurants, cafes, and parks in Boston. Whether it is just a date or a romantic trip to Boston, follow these tips and impress your loved one. Date ideas Boston | things to do in Boston for coupes | romantic hotels in Boston |

Author: Kalyn

Kalyn is a travel writer from Orlando, Florida, with a love for Disney World, street food markets, and finding the best milkshakes in every town. You can read her travel tips on her Pinterest boards.