Romantic Rendezvous: Best Date Ideas in Boston

February 14, 2024 | , , , , ,
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The Best Boston Date Ideas!

Date night is definitely not just for February 14th! Boston can be romantic any of the other 234 days of the year too. We love creative date night ideas and there are tons in Boston. So, we made a list for you! 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 but it’s usually a success if good food is involved, so don’t be surprised if most of our ideas revolve around food.

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. It’s fine…you can take the credit, we’re happy to be your wing-food tour!

22. Dinner and Drinks at Yvonne’s Restaurant and Supper Club

Photo Credit: Yvonne’s

For a romantically sophisticated evening take your date to Yvonne’s Supper Club in Downtown Crossing. The atmosphere is dark and intimate vibe and the food and drinks are 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 as well as a dining room adorned with chandeliers. Whatever you decide the mood will definitely be set *wink*.

21. Play Social Darts at Flight Club Boston

Photo Credit: Flight Club

For a super fun and playful date night idea head to Flight Club for some drinks and darts. This is not just your typical bar darts where half the pieces are broken and there is one sad board. This is like a darts bowling alley with your own little lane. Flight club refers to themselves as “the home of unexpected, ridiculous, joy,” so, expect a great time!

20. Cold Tea for Two at Shojo

Photo Credit: Shojo

If you want to be prim and proper for date night and have a spot of tea, then don’t go to Shojo for Cold Tea for Two! Just kidding, GO TO SHOJO, but don’t expect to be prim and proper. This is no high tea like they do in England, rather a chilled boozy treat hidden in a tea pot with a dash of history.* Oolong tea infused vodka is mixed with peche de vigne, oolong syrup, and lemon. This is not your grandmother’s tea. Or maybe it is! Either way it’s our kind of tea and the perfect drink to start date night off with before diving into their tasty menu.

*To learn the history behind the cold tea you can join us on our Culture & Cuisine of Chinatown Tour.

19. Catch a Movie at Coolidge Corner Theater

Photo Credit: Coolidge Theater

Coolidge Corner Theater is iconic in the Brookline neighborhood and as with many small, local businesses, has a certain charm about it. They specialize in international, documentary, animated, and independent film so the selection is always interesting. Head out to the theater and enjoy a curated film experience with your date without having to scroll endlessly through Netflix.

18. Get Creative at The Clay Room

Photo Credit: The Clay Room

If you want to get a little creative for date night, literally, head to The Clay Room and spend the afternoon or evening painting ceramics with your date. Maybe even paint something for them. This is another great casual date idea to take the pressure off of sitting awkwardly at a restaurant and have some fun being creative. We are big fans of experience/activity dates and especially ones where you can get your hands a little dirty, so add this to your date night list!

17. Take a Cooking Class at Dave’s Fresh Pasta

Photo Credit: Dave’s Fresh Pasta

Food is a love language so get to work making your own dinner for date night at Dave’s Fresh Pasta in Somerville. Dave has been making and selling handmade fresh pasta and ravioli for over 30 years! They offer excellent cooking classes of all kinds so be sure to check their calendar. Of course they are known for their pasta making classes, which is a super fun experience and a great date idea with your partner. If there’s a second date *fingers crossed* you can make what you learned together at home!

16. Stroll Through the Isabella Stewart Gardner Museum

inside museum

Photo Credit: Isabella Stewart Gardner Museum

This romantic haven is tucked away by Northeastern University and it’s truly a delight to experience! This museum is a lovely spot for a date night or day to take in the beautiful artwork, scenery, and horticulture. The museum opened in 1903 and is still a hidden gem in Boston, so head there with your date for a reprieve from the bustling city streets.

15. Attend a Paint & Sip Event with Laurel Greenfield Art

Photo Credit: Laurel Greenfield Art

If you’re looking to brighten up your date night then join Laurel Greenfield Art for a Paint & Sip Workshop at Boston Public Market. Laurel is a Boston-based artist who offers in-person painting classes with drinks! Let your creative juices flow as she guides you step by step through painting some of her favorite foods based on paintings of her own – ice cream, artichokes, and bagels. You’ll probably get hungry in the process so we suggest having some snacks handy – luckily that is easy in the Boston Public Market! Absolutely no painting experience is necessary and all materials are included.

14. Learn to Bake Like a Pro with Flour Bakery

Photo Credit: Flour Bakery

Flour Bakery has been one of our Sweet & Savory South End Tour partners since the beginning and they help make our life a lot sweeter on the daily. Sweeten things up on your next date by taking a Bake Like a Pro class with a seasoned Flour Bakery pastry chef/instructor. They want to share their love of baking (and enjoying!) homemade treats with you! At the end of class, you’ll enjoy the fruits of your labor and have leftovers to take home and share. This date is sure to be sa-weeeeet.

13. Roller Skate at Chez-Vous

Photo Credit: Chez-Vous

Roll right through this date night on four wheels, nope not the kind you may be thinking of. Chez-Vous is a roller rink in Dorchester that is sure to bring the good vibes for date night. Can’t you picture it? Skating hand in hand with your date, how romantic!…That is if you can skate. We love an activity date so definitely check this place out!

12. Order a Local Boston S’mores Gift Box from Bites of Boston

Make date night at home exciting with a s’mores kit from Bites of Boston Food Tours. Especially if you’re a plan ahead-er, this is perfect for you! This gift box represents small local makers and businesses from the Boston area and is so much fun. Make artisanal s’mores with your date while sipping hot cocoa and cozying up by the fire whether it’s inside, outside, or on a TV. Hey, we’ve got optionsss.

11. Weeknight Specials for Two at Bootleg Special

Photo Credit: Bootleg Special

Bootleg Special screams date night! The vibe is always right for a romantic date, friend date, or take yourself out date but on Monday thru Wednesday nights they have set specials for two. They serve Cajun-Asian fusion with a seafood focus, so things are bound to heat up. Choose from the Squid Ink Fried Rice Meal, the Mussel & Shrimp Boil Meal, or the Clams & Shrimp Boil Meal – you can’t go wrong with any of them! We love them sooo much that they are a partner on our South End Happy Hour Stroll.

10. Drink Beer at a Trillium Location

Photo Credit: Trillium

Trillium Brewing Company is a local favorite and a great option for a date day or night. While they opened in March of 2013 with just three employees, they now have over 300 and six locations. This husband and wife team-owned business shares experiences through the lens of a modern New England farmhouse-inspired brewery with their beers. Their locations are beer-garden style so the scene is set for a great date!

9. Getaway without the Getaway Dinner at Mariel

Photo Credit: Mariel

Stepping into Mariel feels like stepping into the tropics without the flight or the bags. This upscale venue serves Cuban specialties and impressive craft cocktails in a dreamy, elegant surrounding. It feels like a supper club collided with a beach and a night club but in the best way. The food is meant to share and some of the drinks are too. You will not want to stop ordering, trust us! This is a romantic and fun place for date night if you want to get out of the house and have not just a delicious dinner but a cool experience as well.

8. Get a Cheese Board Bundle from Formaggio Kitchen

Photo Credit: Formaggio Kitchen

If cheese were a language we’re trying to be fluent. Was that too cheesy? With the help of Formaggio Kitchen, one of our tried and true Sweet & Savory South End Tour partners, that’s possible! Get fancy for date night at home by taking one of Formaggio’s cheese board bundles to enjoy with your date. Some of the offerings include The Taste of New England Bundle, and if you want to take a trip of Italy, Spain or France Bundle!

7. Breakfast in Bed Package from Lincoln Tavern

Photo Credit: Lincoln Tavern

Sometimes date night turns into date morning, or simply just starts that way. Who are we to tell you when to have your date! Either way, if your date goes into the morning hours, let Lincoln Tavern help sweeten things up with their Breakfast in Bed package. These bake at home kits are available for pick up Friday through Sunday every week. They are currently offering Funfetti Monkey Bread and Cinnamon Toast Crunch Cinnamon Rolls. EXCUSE ME?! Yes. That’s correct. We’ll take both.

6. Omakase Date Night at the Shore Leave Sushi Counter

Photo Credit: Shore Leave

If going out to eat for you always brings sushi to the brain, then first of all – us too, and second – we’ve got the place for you. Take things up a notch by dining at the Sushi Counter at Shore Leave for Omakase – a fast and fun take on a tasting menu. If you are not familiar with Omakase, it translates to “I trust you”, meaning you are trusting the sushi chef to curate your meal of approximately 12 courses. Expect a variety of bites including nigiri, sashimi, and tempura and take away the pressure of what to order.

5. Have a Sophisticated Evening at Better Sorts Social Club

Photo Credit: Better Sorts Social Club

Sometimes you just have to have a bougie date – we get it! If that’s the case then definitely check out Better Sorts Social Club in Downtown Boston. They’ve created a space that evokes a familiar warmth, where conversations can unfold over flavorful cocktails and shareable plates. They invite you to join them at the bar or settle into their plush velvet chairs or tufted leather booths and let the energy of your surroundings – of good spirits and gathered friends – take hold. SOLD.

4. Build Your Own Charcuterie Boards at Kured

Photo Credit: Kured

Have a hand in constructing your own charcuterie board that you can take to go for your next date with Kured in Beacon Hill. You can even have a picnic in Boston Common or the Public Garden since it’s right there! Kured is a new local one stop shop for all of your charcuterie needs, and if you’re like us you have many. The seeds for Kured were planted when Gilli Rozynek studied abroad in Madrid, Spain during her time at Boston College. While there, she learned a lot about the charcuterie landscape because it’s so ingrained in European culture. Gilli’s biggest take away was the behind-the-scenes of what the product could facilitate: bringing people together!

3. Great Date Night Menu at Myers + Chang

Photo Credit: Myers + Chang

Myers + Chang, owned by Flour Bakery’s beloved Joanne Chang and her husband Christopher Myers, has long offered their “cheap date night menu” for two but has since changed the name to Great Date Night – and that it is. These menus are available Monday thru Wednesday from 4pm – 9pm and allow you and your plus one to enjoy a night out at a nice restaurant without completely breaking the bank. Choose from the Get Lucky, Fintastic Feast, or the Plant-Based Party for 2. All set meals come with 5 dishes plus rice. Um, can we get it just for a party of one??

2. Elegant Curated Picnic with Pop-up Picnics

Photo Credit: Pop-up Picnics

If you really want to go all out and wow the pants off your date (take that how you like) then you have to book a picnic with Pop-up Picnics. This is not your ordinary red gingham pb&j picnic, this is elevated to a fairytale level. Alissa and Chenoa, the friend-owners of Pop-up Picnics, will curate a gorgeous scene out of a magazine at a location of your choice with everything you may need for the most romantic date.

1. Happy Hour Food Tour with Bites of Boston Food Tours

For one of the best experience dates you’ve ever had, join Bites of Boston Food Tours for local foods, libations, and lots of fun. The South End Happy Hour Stroll offers a refreshing walk around one of Boston’s most interesting neighborhoods where you’ll learn about its rich history and culture while enjoying delicious tastings and drink pairings along the way from local gems. Offered on Wednesday and Friday evenings, you can book on the calendar now!


Editor’s Note: This post was originally published on February 19th, 2018 and has been updated and revamped for accuracy and fresh content.

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