Romantic Rendezvous: Best Date Night Ideas in Boston

February 5, 2019 | , , , , ,
Return to Boston Food and Fun Blog

Romantic Things to Do in Boston

We’re in our last push of winter (high fives all around) and while it may not be spring, it’s February and love is in the air. You could cozy up with your honey at home on the couch or spice things up and head out for a night of fun with a new activity. Date night (or day) doesn’t have to be all about fancy dinners and flowers. Boston has a ton of fun alternative date night options, so get out there and check them out.

Please note, date night also includes friend-dates, so if you’re living that single and free life, don’t feel left out, you’re still invited to the party! Also, if you’ve been waiting to ask someone out, stop waiting and invite them to do one of these awesome activities, you’ll look super thoughtful and creative. Win. Win. And if there’s food involved – Win. Win. Win.

23. Dinner and Drinks at Yvonne’s

table with people and drinks

Photo Credit: Yvonne’s

For a romantically sophisticated evening take your date to Yvonne’s in Downtown Crossing. The atmosphere is dark and intimate and the food and drinks to-die-for. They have a bar/lounge area that looks like an old library where you can sip libations or have a full dinner. Whatever you decide the mood will definitely be set *wink*.

22. Bites of Boston Food Tours

Any activity that involves food is always a fun way to spend the afternoon, especially on a date. No awkward napkins on lap and elbows off table. Take a casual walk around one of Boston’s neighborhoods that is rich with history and culture, and enjoy tastings along the way with your date. This is a unique date-day activity that you’ve got to try out!

21. Catch a Movie at Coolidge Corner Theater

outside theater at night

Photo Credit: @sweetbabyjamjam via Instagram

Coolidge Corner Theater is iconic in the Brookline neighborhood. It’s the ideal spot for a casual yet cool date. They have been specializing in international, documentary, animated, and independent film for years. It’s not out of the ordinary to see a throwback film listed on the lineup outside. Around Halloween they hosted two showings of “Hocus Pocus” that filled up!

20. Get Creative at Clayroom

couple with pottery

Photo Credit: The Clayroom

If you want to get a little creative for date night, literally, head to the Clayroom and spend the evening painting ceramics with your date. Maybe even paint something for them. This is another great casual date idea to take the pressure down a few notches and have some fun. It’s always easier to be yourself on a date when you are doing an activity so try it out.

19. Dinner at the Top of the Hub

table view

Photo Credit: Top of the Hub

For a truly romantic evening, dinner at the Top of the Hub in the Prudential Center is the place to go. The expansive view of the city from high up is sure to cause some heart flutters. While we usually say that fancy is not necessary for date night, we couldn’t leave this one off the list. Often times there is also live jazz music to set the mood.

18. Isabella Stewart Gardner Museum

inside museum

Photo Credit: Isabella Stewart Gardner Museum

This romantic haven is hidden by Northeastern University and a reprieve from the bustling city streets. This is a lovely spot for a date night or day. The museum is not huge so no worries about getting bored, just go for a nice, slow walk and enjoy the scenery without having to freeze outside!

17. Gondola di Venezia


Photo Credit: Boston Gondolas

Set romance afloat on the Charles River. Gondola di Venezia offers a variety of romantic tour packages on the Esplanade to woo your S.O. This is a unique experience for us North-easterners and we highly recommend checking it out; you’ll feel like you’re in Italy. And if you don’t we guarantee your points in the date department will sky rocket.

16. Dollar Oyster Date


Photo Credit: Island Creek Oysters

If you want to go with this classic aphrodisiac for date night why not have as many as possible? Boston offers a ton of one buck shuck spots throughout the week so you can get in the mood without breaking the bank. Check out this list for tons of options for dollar oysters in the city.

Want more? Check out the weekly shucking classes at B&G Oysters to sharpen your oyster skills. Talk about impressive. Ow, ow.

15. Candle Pin Bowling & Flatbread at Brighton Bowl / The Flatbread Company

bowling ally

Photo Credit: @corinnediz via Instagram

Sometimes it’s fun to go out on a goofy date and loosen up a bit. Candlepin bowling is perfect for this scenario! It’s basically bowling but with super thin pins and smaller bowling balls. Have a drink or two and everyone becomes good at bowling, or at least is under the illusion that they are. Brighton Bowl is an awesome place to do this because they are joined by The Flatbread Company, serving artisanal, mouthwatering flatbreads that are worth the trip alone.

14. Hot Tub at Inman Oasis

japanese hot tub

Photo Credit: Inman Oasis

Want to have a bit of a left-of-center date? Those are the kind of dates that we love! Have a romantic and bubbly evening in one of the private hot tubs at Inman Oasis. They have two to choose from and you can bring your own playlist. It gets hot and steamy in there (literally) so you won’t even have to try that hard to heat things up. You will feel sooo relaxed after. We actually just dozed off writing this blurb.

13. Shakespeare on the Common

shakespeare on the common

Photo Credit: @commshakes via Instagram

For a romantic night out in the warmer weather, head to Boston Common for a free Shakespeare performance. Bring a blanket and a picnic and enjoy the show. To eat or not to eat? Honestly, that is never a question. Go all out with the snacks, your date will be impressed with dinner and a show on the cheap!

12. Beer and Fun at Lamplighter Brewing Co.


Photo Credit: Lamplighter Brewing Co.

Lamplighter is a hip brewery with lots of ideal happenings for a fun date night. Check out their event calendar to find something you fancy. Their events range from trivia night to calligraphy class to pierogi pop-ups. There’s really something for everyone. And when all else fails, which we hope it doesn’t, their beer is fantastic!

11. Game Night at Knight Moves Cafe

board game cafe

Photo Credit: Knight Moves

Let out your quirky side, which we can’t deny is in all of us, and take your date to Knight Moves, the board game cafe in Brookline. It’s all fun and games until someone’s a sore loser and throws all the pieces. Seriously though, board games are a blast and sometimes it’s nice to put the screens away and get a little old school.

10. Cocktails and Small Plates at Cuchi Cuchi

cocktail and app

Photo Credit: Cuchi Cuchi

Take your date to another era for some small plates and cocktails at Cuchi Cuchi. You’ll forget you’re in Boston and definitely think you were sent back to age of Old World Beauty and Early Hollywood. The decor is representative of that era and the staff is dressed to match as well. The space is an adventure and the menu will take you around the globe with its tapas selection. For a special date night definitely spend it here.

9. See A Movie and Dine-in at Showcase SuperLux Chestnut Hill 

cocktail in movie theater

Photo Credit: @mikewendt via Instagram

Feel like a movie night but want to be a little fancy? Take your date to the Showcase SuperLux Theatre in Chestnut Hill for a posh movie experience with cushy, reclining chairs, food and drinks delivered right to your seat, and the opportunity to order alcohol. Large popcorn and a cocktail alongside it? Now that’s our kind of movie!

8. Take a Couple’s Cooking Class with Selfup

couple in aprons

Photo Credit: Selfup

One of the best ways to get to know someone is to cook with them. While this could be a make or break situation, it’s usually a great success. Learning together is fun and eating what you make is an even better reward. Shake up date night and sign up for one of the many cooking classes offered in Boston through Selfup. Who knows you might even be able to take your skills home to host the next date night in.

7. Omakase Menu


Photo Credit: Pabu

For a romantic and fun food adventure-type date head to one of Boston’s restaurants serving Omakase menus. Omakase is a Japanese term for a meal consisting of dishes selected for you by a chef, a tasting menu if you will, of sushi-like items. This is a very special, splurge experience for some but totally worth it if you want to impress your date and have an intimate meal where you can really take your time and enjoy. A couple of great places with Omakase menus are Pabu and Uni.

6. Daybreaker Event

group fitness

Photo Credit: Daybreaker

If you’re having trouble finding time to have date night, why not have date morning? Daybreaker is “an early morning dance movement” that is now in 22 cities, including Boston. It starts super early but is a blast! It all begins with a one hour yoga or fitness class, and is followed by a two hour dance party. You know you want to…

5. Cheap Date Night at Myers + Chang

table with food

Photo Credit: Myers + Chang

On Mondays and Tuesdays Myers + Chang offers a “cheap date night” menu for couples trying to save but feel like they’re splurging. Each menu is designed to be a full dinner for two and costs $45 total. The three choices are: “Netflix + Chill,” “Tango Lessons,” and “Long Walk On The Beach.” Points for humor!

4. Arcade Games and Awesome Cocktails at A4cade


Photo Credit: A4cade

For a true night of fun head out to A4cade in Cambridge for date night. This adult arcade sells playful cocktails and is ideal for a stress-free night out with your S.O. Feel like a kid, but remember that you are an adult as you sip your cocktail from a colorful bendy straw, ha!

3. Drinks and Snacks at Lolita

This dark and trendy spot is made up of Day of the Dead decor with a gothic spin. There is a certain magic about this place, which makes it perfect for date night. Sip tequila-based cocktails and have some modern renditions of traditional Mexican snacks. It feels like such a big step away from the streets of Boston it’s easy to get lost in the atmosphere here.

2. Sign Up For A Craft Night through Yaymaker

Get crafty for date night and sign up for one of the cool classes offered by Yaymaker. You can make succulent terrariums, candles, and more! This is a really fun and creative date idea and perfect for those people that are either tired of or not about those conventional kinds of dates.

1. Curling and Cocktails at The Liberty Hotel

group curling

Photo Credit: @thebull1017 via Instagram

One of our favorite spots for an intimate date night evening is the Liberty Hotel. It’s so much more than just a place to sleep, it has a whole bustling nightlife. From the six restaurants and bars that it has to the events it offers there is something to do every night of the week for date night. They currently have a curling rink set up where they are offering complimentary curling. If you’ve ever watched curling in the Olympics and said how do they do that? Well, go try it out for yourself, and bring a date! To make this an even more fun date night spot, they have a special curling cocktail menu with drinks like The Bonspiel and Stone’s Throw.

Tags: , , , , ,

Published by

Return to Boston Food and Fun Blog