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.

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

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. 

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. 

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. 

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.

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.

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. 

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.

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.

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.

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.

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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!

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