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Dating in Boston Tips

Do you need some great date Ideas in Boston? Boston is an amazing city with tons to do but sometimes my clients get stumped on what to do now that they have their first date. Maybe you’re in the same boat and you need some inspiration!

If you really want to impress your partner, you’ll want to take them somewhere they haven’t been before, or somewhere that gives them a different view of the city they’ve never seen. Since I know you’ve taken advantage of my excellent conversations starters 😉 I know you’ve learned a great deal about what your date is interested in and what kind of thing he/she likes to do, eat and see? Now is the time to impress them with your in-depth knowledge of the city and all it has to offer. Now is not the time to be shy so let’s show them a side of the city they may not have seen before.

One little caveat, I usually do not recommend that you “surprise” your date on your first meeting. It’s better to be specific and what you’re planning so they know how to dress or if they need to discuss your restaurant choices ..it’s just better to be safe on the first date.

Oh and if you’re reading this in the hopes of finding a date in the Boston area, then check out our guide to finding Dating Photographers in Boston to help you score the best dates possible. After all , it’s all about that important first impression and a professional profile photo will make you stand out from the crowded Boston dating scene

Here are some of the best date ideas in the city, to really help you hit it off.

1. Throw Some Axes Together
Did you know that you can throw axes just like a seasoned lumberjack, right here in Boston? You can when you go to Revolution Axe Throwing. This unique venue gives you the chance to learn how to throw axes and compete against your date in order to get the best score.

If you think your date is up for something a little quirky and dangerous, then this will be right up their alley. Reservations are an hour long, more than enough time for you both to get in few throws, and you’ll be directed by professionals. Afterwards, there lots of local breweries where you can go for a drink too.

2. Visit The Isabella Stewart Garner Museum
Is your date into history and culture? Then in Boston, you’ve no shortage of historical sites to take them to. If you want to find the most romantic museum though, the Isabella Stewart Garner Museum is it! As well as rooms packed to the brim with art, there’s also a courtyard that’s full of flowers and other greenery, perfect for a romantic stroll.

The best time to go is on Thursdays when the museum is open later in the evenings. Every third Thursday, you’ll also have the chance to go to themed events. These feature resident and visiting artists, so you’ll want to check it out.

3. Take A Stroll In A Cemetery
Yes, really. The Mount Auburn Cemetery is the final resting place of many famous names, making it a fascinating walk for anyone into history. If your date is into this kind of thing, they’re going to love it here.

That’s not all there is to the area, though. With 72 acres on the site, you’ll also find an arboretum and a wildlife sanctuary, which are going to be amazing backdrops for a quick selfie or two.

4. Watch A Game At Fenway Park
Are you really on a date in Boston if you don’t go watch the Sox play? Fenway Park is one of the most famous baseball parks in the country, so going there to take in a game is a great way to spend a date.

Once the game is over, you can go celebrate or drown your sorrows in any of the nearby bars. Eventide or Audubon are excellent choices for a drink or two post game.

5. Ride The Minuteman Bikeway
If you’re on the hunt for an active date idea, this one is perfect for you. This is an 11 mile route from Bedford to Fresh Pond, and if you’re both active people you should easily be able to do it in one go. Once you get there, you can explore the Lexington Battle Green, Arlington’s Great Meadows and North Cambridge’s Alewife Brook Reservation.

You can finish off your date by heading to Talulla, a small but highly popular Italian restaurant to fuel up before you head back.

6. Indulge In A Spa Treatment
For a date night you really want to splash out on, look no further than the Mandarin Oriental. You can book spa treatments in the couple’s suite, right in the heart of this opulent hotel. The suite itself has a huge soaking tub and sauna, perfect for relaxing in.

The Asian-inspired treatment room also has to be seen to be believed. You’ll be able to get a personalized spa treatment in your package, and once you’re done you can book dinner at the Bar Boulud.

7. Take A Cruise
As you’re in Boston, one of the best ways to see the city is by boat. You can book a boat tour for your date that has everything you need for a romantic evening. Tours depart from Rowes Wharf, and sail around Boston Harbor.

Your tour will come with a three-course meal, live music, and a DJ to start the party. You can throw shapes together on the dance floor, or you can get onto the deck and take some truly romantic photos together. What better backdrop could you have?

8. Take In Some Immersive Art
Here’s another great suggestion if your date loves art and wants to try something different. The ICA Watershed is home to many exciting, large scale installations. These change out all the time, so you can see something different every time you go. Right now, for example, you can go see the Firelei Baez installation, where the space has been transformed into an ancient ruin.

9. Take Time For A Picnic
Sometimes the simplest date ideas are the best ones, so why not take your date on a picnic? The South End is one of the best places to enjoy some alfresco dining, with plenty of places to pick up all the necessities you need. Then, head to Titus Sparrow Park to enjoy the green space as you eat. If you want some ideas on how to plan the perfect wine picnic, then I recommend you check out this Wine Picnic video it will tell you everything you need to know to plan and execute the most memorable picnic for your date.

10.Take A Walk
Another very simple date idea is to take a walk along the iconic Habor Walk. After all, Boston is America’ Walking City, so why not get on your feet and see what that the city has to offer you? You’ll be able to see the Fort Point Channel and Seaport on your walk, before stopping to watch the boats on Fan Pier.

When you start heading back, follow the Rose Kennedy Greenway to see some modern art installations. You can finish up by heading for a beer at one of Boston’s many breweries.

11.Hit The Shops In Back Bay
Want to take your date on a spending spree? Then Back Bay is the place to do it. There’s so many unique stores here, such as Newbury Comics, Shreve, Crump & Lowe, and Simon Pearce.

Once you’ve shopped till you dropped, you’ll be able to take your pick of fantastic restaurants to dine at. Sonsie is a favorite here, especially with couples. Table 12 here is known as the Engagement Table, as it’s a popular request for locals looking to pop the question.

12.Try Out Darts When Dating in Boston
Flight Club is a bar and darts club that’s unlike any other you’ve experienced. While some bars are kind of seedy and may not even have all the pieces for the game, this is a sleek and modern take on darts.

Here, you’ll get your own lane and have a great time competing against each other to get the best scores. If you’re both competitive, it’s something you’re bound to both enjoy.

13.Visit The Coolidge Corner Theater
If you want to head to a cinema date night with a difference, then you have to go to the Coolidge Corner Theater. They are a gorgeous art deco-styled theater that specializes in international, documentary, and animated movies. If that’s your thing, then you’re going to love your date night here.

Right now, the cinema is offering virtual experiences. Even if you aren’t able to visit in person right now, you’ll still be able to enjoy what the cinema has to offer.

14.Try A Meal Kit Date
Do you and your date like cooking? Do you both want to cook more, but never have the time? Then why not try a meal kit service? There’s so many out there, there’s bound to be one that’s for you.

One that we would recommend would be Fork On A Road, a local business that offers vegetarian meals that are mostly based on Indian and South Asian cuisine. It’s a lot of fun to cook together, especially if you’re just getting to know each other. Why not give it a try?

15.Take A Walking Food Tour
Speaking of food, you know that Boston is packed to the brim with food and drinks venues. If you want to get the most of them with your date, then you’ll want to check out Bites Of Boston Food Tours.

They will take you around some of Boston’s most interesting neighborhoods, showing you what’s on offer and helping you get a taste of the local flavors. It’s an excellent way to spend a date, and you’ll pick up some new restaurant tips on the way.

16.Create Something New At The Clay Room
Want to try a date night with a difference? Then you’ll want to book a spot at The Clay Room. As the name implies, it gives you the chance to paint ceramics with your date. It’s a great date option as it’s relaxed, creative, and you’ll be able to get your hands dirty. If that sounds like you’d both love it, then get in there now. Once you’re done, you’ll have your own painted piece to take home with you.

17.Learn To Shuck Oysters
Here’s another slightly offbeat date idea that you’re going to love. Everyone knows that oysters are a classic aphrodisiac, so why not learn how to shuck them yourself? You’ll be taught by a seasoned pro, and then given a dozen oysters to practice on. You’ll also get two glasses of champagne to enjoy during the process, too. Once the event is over, you’ll have instructions to take home too.

This is always a fun night with your date, and you’ll learn something during it too. What could be better?

18.Experience Shakespeare For Free
What’s better than a free date night? The Commonwealth Shakespeare Company are putting on free shows on the Boston Common, an amazing way to experience the Bard. It’s especially great in the summer months too, as you can go take in some air, take a picnic with you, and even a closed container of something if you’re feeling it. Right now, they’re putting on a production of The Tempest, so go see when the next play is.

19.Head To A Concert At The Library
Did you know that the Boston Public Library hosts free concerts? They cover all kinds of genres, from classical to blues, jazz, folk and more. Whatever you’re into, there’s bound to be something on the docket that you’ll love. These concerts are usually held in the courtyard, so it’s another amazing outdoor date night for you both.

These concerts happen both at lunchtime and in the evening, so you can have a more laid-back midday date, or you can kick it up a notch in the evening, going for dinner before and drinks afterward.

20.Take On Fitness Classes Together
Are you both into fitness? You’ll want to know if you’re compatible fitness-wise, and there are lots of ways to do that in Boston. There’s the November Project, which is holding early morning large-scale workouts outdoors. There are lots of free workouts in the parks of the city too, so take a look around and see what’s out there. There’s bound to be something you’ll both enjoy.

21.Go To A Drive-In Movie
Recently we’ve all rediscovered the pleasures of a drive-in movie. Just roll up in your own car and enjoy the movie snuggled up together on the front seat. What could be better?

Boston has embraced the trend in a big way, with Mendon Twin Drive-In offering double features. They show both throwback movies and new titles, so you can experience something fun and different. They even have a snack bar and beer garden too, perfect for when the movie’s over and you just have to dissect it together.

22.Take A Walk Around Beacon Hill when You’re Dating in Boston
This is another super basic date idea that really gives you a lot of space to enjoy each others’ company. Beacon Hill is a stunning area of Boston, and taking a walk around it on a Sunday afternoon is a great date idea. It’s even better when you go at night and everything is lit up.

You can check out the brownstones, and look through all the little shops that are in the area. It’s a great way to get to know each other, with no pressure.

23.Go See The Seals
Did you know that there’s an outdoor seal exhibit at Boston Harbor? It’s run by the New England Aquarium and offers you the chance to get up close with the seals and watch them in their natural habitat.

There’s more to see to at the aquarium itself, with lots of aquatic life on display. An aquarium is always a fun way to spend an afternoon on a date, so why not go along one weekend and check it out?

24.Pick Your Own Flowers
Who doesn’t love being given a bunch of flowers by their date? It’s even better when you’ve picked them yourself. You can head to Land’s Sake in Weston and pick your own flowers, as well as vegetables and herbs. It’s a great way to stock up, while getting to know each other.

There’s also a farmstand here with plenty of goods that you’ll want to take home with you too, such as fruit and honey.

25.Enjoy The Outdoor Market At Union Market
The Union Market has everything you want from an outdoor market. With summer here, you can enjoy the good weather and get in some great window shopping with your date. There’s a good range of outdoor dining and breweries too, so there’s everything you could want in a date here.

26.Try A Walking Tour when You’re Dating in Boston
There are plenty of self-guided tours that you can take around Boston, and they’ll all help you understand the rich history of the city. You can download multiple different tours, so you can pick one that you think your date would like. There’s the Freedom Trail tour, the Black Heritage Trail, or the Women’s Heritage Trail to name a few. With so many here, you can spend hours exploring Boston and learn something new, too.

27.Enjoy Central Square
Central Square is an amazing place to enjoy a date, as there’s so much to see and do there. You can start with dinner in one of the many restaurants here, including Pammy’s which features a huge vintage shared table. Once you’re done with dinner, you’ll be able to head down Graffiti Alley and take in music, live comedy or more. Whatever you’re looking for, you’re going to find it here.

28.Pick A New Area And Check It Out
Is there an area of Boston that you haven’t seen yet? There’s so much packed into the city that there’s bound to be somewhere you and you date haven’t explored. Take the time to go somewhere new and thoroughly explore it.

There’s so much to see and do in Boston, it’s the perfect place for a date night. Pick any date off this list and try it, or work your way through them all. You’ll experience so many new and different things, and you’ll be able to get closer together too. What could be better? Plan your Boston date now and see what the city has to offer you both.

With these great date Ideas for Boston, I’m sure you’ll impress your date and make sure you get the second date ..if that’s what you want. The truth is there are lots of great date ideas in Boston and the surrounding area. It’s important to express your creativity and not just default to dinner or a movie. First dates are fun ways we get to know someone in an enjoyable atmosphere where you can talk and experience an event or location together. After all that’s how memories and relationships are built ..one shared experience at a time!

About the Author

Lauren Groff is a writer specializing in small businesses, working with Essay Writing Service and Academized. She focuses her writing on dating and relationships.