50 Best Date Night Ideas in Boston, Massachusetts!

Date night! The best night! Even if you've been together for years and years, date night is still so important and refreshing. Especially in the middle of a cold Boston winter, date night is important to heat things up. So whether it's Valentine's Day or your birthday or just because, here are some ideas to snuggle up with your sweetie and let them know how important they are to you. And if you're living that single life, these are fun activities to do as well - with a cherished friend or to meet a new one. The City of Boston and beyond in Massachusetts has so many amazing activities for you to enjoy!
A couple smiles while standing in front of a tiled wall on an Off the Beaten Path Food Tour in Harvard Square.

Our 50 Best Boston Date Night Ideas:

1

Catch a Show at awesome theater such as Calderwood Pavilion

 

2

A Chocolate Tour or Food Tour Experience!

 

3

Learn A New Board Game

 

4

Go 80’s with a trip to an Arcade

 

5

$1 Oysters!

 

6

Find a Fireplace to cozy up to

 

7

Catch a late night movie

 

8

Stare at the stars at a local astronomy open house

 

9

Try a new recipe at home

 

10

Create your own wine tasting or brewery experience

 

11

Splurge on last minute tickets to a concert

 

12

Try a cooking class

 

13

Visit the Boston Aquarium’s penguins and IMAX

 

14

Be adventurous on Indoor Race Tracks at F1

 

15

Finally try rock climbing – you can do it!

 

16

Try a “southern” style romance with honkytonk and biscuit brunch

 

Date night ideas in Boston continue…

 

17

Book a vacation together!

 

18

Try black light yoga — most people can’t see you if you stink

 

19

Head to a casino and play bingo

 

20

Take a beach walk, even in the winter

 

21

Take a cycling class and splurge on some fresh fruit smoothies

 

22

Make a long mix on Spotify and take an evening drive together, blasting it

 

23

Stroll down our favorite street, Memorial Drive in Cambridge

 

24

Check out a new cool area of Boston – have you been to the Innovation and Design Building in the Seaport lately? Try Chickadee!

 

25

Create a bubble tea “passport” and try and compare them over the course of a week: from China Town to Allston to Kung Fu Tea in Davis Square!

 

26

Visit a farmer’s market — indoor, outdoor, yum!

 

27

Order delivery from a really fancy place, using Postmates or something like Puritan Trading company or Scoop N Scootery

 

28

Visit a local cheese shop with no budget — throw those delicious fig flatbread crackers in the cart, various fruit jams, specialized honey, local cider, and alll the cheese!

 

29

Hit up record stores and also estate/yard sales searching for amazing tunes

 

30

Plan a day trip to a place 30-90 minutes away. Whether it’s one of our Food Tours such as our Lowell Tours or cool spots around New England, it’ll feel like a longer vacay.

 

Want more unique date ideas in Boston? Continue reading!

 

31

Comedy Night!! From the Comedy Studio in Somerville to Improv Boston, get your belly laughing.

 

32

In warmer weather, rent a sailboat such as at the JP Boathouse – we also have a Jamaica Plain Vegan Chocolate Tour and also a Jamaica Plain Food Tour

 

33

Escape the room! Whether it’s on your new Alexa or at Boda Borg in Malden, we’re game!

 

34

DANCE! Shake your booty around town, and if you need encouragement for the classics check out some dance lessons

 

35

Go ring shopping 🙂

 

36

Get your booty off Amazon.com and go mall shopping like it’s 1999

 

37

Splurge on a tasting menu at a local restaurant – hopefully the chef will say “hi”

38

Spa it up — we’ve written about salt caves, indoor hot tubs, couples massages, and more!

 

39

Try your hand at arts and crafts — take a local class such as glassblowing!

 

40

Embrace your inner animal lover at a local zoo (cotton candy optional)

 

41

Seriously, try one of our historical neighborhood walking and food tours!

 

42

Wander through indoor markets together, from Formaggio to Eataly to Boston Public Market

 

43

Indulge in afternoon tea (see our post)

 

44

Take a ferry ride — such as to Boston Harbor Islands or Charlestown or even P-Town!

 

45

Live that island life, plan a trip to Nantucket or Martha’s Vineyard

 

46

BRUNCH! We love brunch and the word foodie. So there!

 

47

Learn how to mix drinks together

 

48

Try a Tai Chi class and feel centered together

 

49

Host a murder mystery party — costumes and secrets galore!

 

50

Hot air balloons? Skydiving? Take your adventure to the skies!


Our Food Tours and Chocolate Tours run weekly year-round and are the best Boston date night activity. Our guides are warm and welcoming, and you’ll discover hidden gems all over the city. Book today at www.offthebeatenpathfoodtours.com and visit the Tour Calendar to pick a date.

Share this post:

Share on facebook
Share on twitter
Share on pinterest
Share on linkedin
Share on email

If you like this post, you'll love

browse the blog
  • Neighborhood

  • Categories

recent posts