date ideas

Best Outside-The-Box Date Ideas In And Around Boston

Whether it’s your first date or your hundredth, spending time with your special someone is always precious. There are so many nice ways to show your significant other how much they mean to you—but nothing does it better than taking the time to come up with something totally different and unique to do together. From learning to paddleboard to trying an escape room together, to the real show stoppers, these experiences are meant to tighten the bond between you.

Check out these top picks for the best outside-the-box date ideas in and around Boston.

#1 – Learn how to make cocktails at No. 9 Park

Cocktail making classes are a fancy way to get tipsy on a date. They are also a great way to learn how to make awesome cocktails at home. No. 9 Park has a monthly cocktail making workshop held on Sundays from 2:00–4:00pm. Their cocktails are thoughtfully arranged and nicely crafted, perfect for an outside-the-box date idea.

cocktail making date ideas
#2 – Spice things up in the kitchen at Stir

Cooking with the one you love is one of the best romantic experiences you can have. Not to mention learning new skills—and new recipes—is necessary if you want to maintain a good relationship with your kitchen too. At Stir, you can learn how to prepare the most complicated dishes in most simple of ways. This lovely cookbook cooking studio has regular hands-on and demo classes. Take a Rosé, Corn, and Potato class or experiment with puffy pastry.


#3 – Escape from Trapology Boston

Escape rooms are awesome, and if you haven’t been to one before you have no idea what you’ve been missing. Check Trapology Boston, centrally located in downtown Boston, with two fun escape rooms to choose from: Drunk Tank and The Hustler. Either bust out of the your local drunk tank or avoid the triads at a popular gambling house who are trying to collect on your debts. The game play is exciting and engaging, and the puzzles are thoughtfully put together, making this date idea something fun and different that also won’t be too hard on your wallet.

#4 – Go out for the night of painting and drinking

Paint nights are a nice way to show off your creative side and have a different night out. The Paint Bar has paint nights for $35 and a full bar as well where you can purchase beer and wine. The format of the paint class is laidback and friendly. No matter how little experience you have actually painting, you’ll do just fine.

chocolate tour date ideas#5 – Go on a sugar rush tour with Boston Chocolate Tours

Couples with a sweet tooth can go on a chocolate tour of Boston for a fun evening date idea. Sounds crazy, but Boston Chocolate Tours specializes in sweet guided tours where you can try a bunch of different types of chocolate, cupcakes, ice cream, and even get a chocolate-inspired alcoholic drink.

#6 – Surprise your date with a Laser Quest date night

A bit outside of the city, Laser Quest is open late for evening games—super important if you want to enjoy an indie retro date without lots of hyper children running around. Check out their Iron Man games on Fridays and Saturdays from 9:20pm to avoid the kids.

#7 – Try rock climbing together

Fit couples and those looking for something active to do can drop-in at Rock Spot Climbing South Boston for a climbing lesson. This rock climbing gym might just become your local afterward for their competitive pricing and friendly atmosphere. They have a lot of special deals, like late night climbing for $18, perfect for an evening date idea.

#8 – Take a SUP class and learn to stand on water

For a fun day date idea, Charles River Canoe & Kayak offers a 90-minute standup paddleboard lesson that will teach everything you need to independently go paddleboarding later. You will learn about basic strokes, safety in the water and see the beauty of this sport. Special bonus: have a good laugh when one of your falls in!

Helicopter tour date idea#8 – Enjoy the view and have fun on a helicopter tour

If you’re planning to celebrate an engagement or an important birthday, or to totally sweep someone off their feet, a helicopter tour is the perfect showstopper. Blue Hill Helicopters specializes in luxurious and professional tours of Boston and greater Boston area. Take a sunset tour and enjoy view.

About Hijinks

Hijinks is the online marketplace that makes it easy to discover and book life experiences to enjoy with friends, family, and co‐workers. Whether it’s an escape room visit, cooking class, or team building activity, we provide comprehensive listings, customer ratings and reviews, and easy browse and search functionality to help you book with confidence. For more information check us out here!

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