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Whether you are about to go on your first date or you are just looking to spice up date night with your long-term partner, I’ve got you covered! I’m here to help take out the guesswork revolving around Boston date ideas so you’re not stuck with another “Netflix and chill” weekend. The list below includes year round Massachusetts date ideas based on shared interests so you’ll never be stumped for a fun night out again.

If you need more ideas on things to do as a couple in the Boston Seaport District you can click here and if you are looking for more ideas on a weekly basis then check out Thrillist’s Boston Things To Do This Weekend article.

stylish couple walking down an alley  holding hands in Boston's Beacon Hill neighborhood

Boston Coffee Shop Dates

Coffee dates are great when meeting up with someone for the first time, but you don’t want to be stuck in a place that doesn’t have a lot of seating, menu options, or will be too loud for you to hear your date sitting across from you. Tatte Bakery & Cafe, Pavement Coffee, Thinking Cup, and Trident Booksellers & Cafe are based all around Boston and have that cozy ambiance you’re looking for. Each spot also has food options so you can grab a bite if things are going well! Currently with COVID Trident Cafe is the only coffee shop that you can sit down in, but feel free to grab to-go drinks from the other and take a stroll around the city.

stylish couple walking down an alley  holding hands in Boston's Beacon Hill neighborhood during their engagement session

Boston Museum Date Night

Soak in some culture and marvel at the artwork at these popular Boston Museums. The ICA (Institute of Contemporary Art), the MFA (Museum of Fine Arts), Isabella Stewart Gardner Museum, and the Museum of Science all offer something for everyone. Top tip- if you have a library card you can get huge discounts on admission tickets for any of the above museums listed as well as the Boston Aquarium.

stylish couple touching foreheads leaning up against a brick wall during their Beacon Hill engagement session

Boston Water-Based Date Ideas

There are lots of fun options when choosing a water based activity whether you are looking to take a sunset cruise around the harbor, catch a whale watch, or paddle out yourself. I’d highly recommend looking into the Boston Harbor Cruise or take advantage of a day trip to Provincetown or Spectacle Island.

Similarly, if you and your date want to go kayaking or take a surfing lesson together then check out these businesses: Charles River Kayak, Cape Ann SUP, Levitate Outdoors, LL Bean Outdoor Discovery Programs.

stylish engaged couple kissing on acorn street during their beacon hill engagement session

Gluten Free & Dairy Free Restaurants for your Date with Food Sensitivities

As someone with food allergies myself sometimes it can be super hard for a significant other to try and guess which restaurants have menu options I can eat- so I always let them know options!

If you want to find a dairy free ice-cream store: FoMu, Pressed Juicery (their vegan soft serve freeze is basically like making an ice-cream sundae) Amorino Boston has some dairy free gelato

Healthy Restaurants: Life Alive, Whole Heart Provisions

Desserts: Flour Bakery, Jennifer Lee’s Gourmet Bakery at the Boston Public Market

Pressed Juice: Mother Juice

a fashionable couple holding hands facing the camera and smiling in front of a bright red door during their beacon hill engagement session

Date Ideas Boston: Go Rock Climbing

There is nothing that speeds up the trust process more than putting your life in someone else’s hands (as long as they have their belay certification of course). Whether you are a seasoned climber or want to give the sport a try there are lots of fun spots to go rock climbing with your adventure partner. Each location provides rental gear so don’t stress about not having the proper equipment. You can choose between bouldering (these routes are lower to the ground and don’t require ropes) or top rope climbing (these routes are taller and require a rope & harness).

Brooklyn Boulders (bouldering routes are lower to the ground and don’t require ropes)

Central Rock Gym (Boston location is bouldering only, whereas the Randolph location offers both bouldering and top rope)

Rock Spot Climbing (offers a mix of bouldering and top rope options)

MetroRock Climbing Center in Everett (offers a mix of bouldering and top rope options)

If you are looking to learn some new skills from climbing to mountaineering in the great outdoors then sign up for a trip with Northeast Mountaineering based in New Hampshire.

two photos side by side of a couple walking up acorn street during their beacon hill couples session
a guy kissing a woman's forehead on acorn street during their beacon hill engagement session in Boston

Massachusetts Date Ideas: Picnic in the Park

Grab your favorite take-out (or really wow your date by purchasing La Jolie’s Romantic Picnic set up) to enjoy a picnic in the park with your loved one. Some wonderful park options include the Boston Common, the Boston Public Garden, the Esplanade, Middlesex Fells, the Arnold Arborteum, the Emerald Necklace/ Back Bay Fens, the Bunker Hill Monument, or various spots in Blue Hills such as Houghton’s Pond.

two photos side by side of a stylish couple sitting on the steps of a charming brick beacon hill apartment during their boston engagement session
two photos side by side of a stylish couple sitting on the steps of a charming brick beacon hill apartment during their boston engagement session

Artsy Date Ideas in Boston

If you or your significant other has a creative soul then you should have a paint night together at Muse Paint Bar or make candles at The Candle Bar. Open Sundays May through October, So Wa Market is another great option to spend an afternoon together. It consists of art studios, a craft fair, farmers market, and has food trucks- what more could you want!

a fashionable couple in a suit and dress standing holding hands in the middle of a Beacon Hill crosswalk during their fall Boston engagement session
an engaged couple arm and arm laughing during their Boston Public Garden engagement session

Boston Markets

As previously stated SoWa is art studios, a craft fair, vintage market, and farmers market all in one. If your sweetheart loves supporting local businesses you should also check out the Boston Public Market and Bow Market in Somerville.

two photos side by side of a stylish engaged couple arm and arm and kissing under the tress of the Boston Public Garden during their couples session

Dancing Spots in Boston

Whether you have two left feet or not, dancing can be such a fun option for a Boston date night.

Looking for line dancing? Head to Loretta’s Last Call by Fenway

Want to salsa? Head to the Havana Club

More into tango? Then check out the Boston Tango Calendar

guy with his arms wrapped around a woman in a white dress laughing during their Boston Public Garden engagement session
black and white photo of a guy with his arms wrapped around a woman in a white dress laughing during their Boston Public Garden engagement session

Boston Comedy Clubs

Curious if you and your date have the same sense of humor? Spend the night laughing at Laugh Boston for touring stand up acts or at the North End’s Improv Asylum. Want to try it out for yourself ? At either location you and your date can sign up for stand up or improv classes!

two photos side by side of engaged couple with their backs to the camera holding hands during their Boston Public Garden engagement session
two photos side by side of a couple standing with their backs facing away from the camera and a close up of their hands during their downtown boston engagement session

Unique Boston Date Ideas For Those With A Competitive Side

These date options help facilitate some friendly competition between you and your partner. Test your knowledge at one of Boston’s Escape Rooms such as Trapology or hope for good aim at Urban Axes in Somerville or Revolution Axe in Everett. If you are looking for other fun things to do in Boston for date night then go bowling! Your best option for food and fun is Brighton Bowl located in Flatbread Brighton.

creative engagement photo of a couple holding hands but focusing on the duck swimming in the water of the Boston Public garden
black and white photo of a man kissing his fiancé's cheek on the bridge in the Boston Public Garden during their engagement session

Boston Foodie Date Ideas

If your date considers themselves a foodie, then you two will have a blast divulging in the local cuisine of your own backyard. Check out the “Bites of Boston Food Tours” and select between Classic Boston, Chinatown, Allston, and South End routes. Got more of a sweet tooth? Head to Somerville for the Taza Chocolate Factory Tour to learn the history of the company while enjoying various chocolate samples.

two photos side by side of a couple hugging and the man lifting her up for a kiss on the Boston Public Garden foot bridge during their boston fall engagement session
couple wearing fancy outfits holding hands at fan pier park during their boston seaport engagement session

Massachusetts Date Ideas For The Sports Enthusiast

Boston is known for its sports culture so catch a game to watch the New England Patriots, Celtics, Bruins, or Red Sox play. If you are looking for a more budget friendly date alternative you can tour Fenway Park or watch one of the Patriot’s training camp practices during the summer for free.

dressed up couple laughing holding hands during their boston seaport district couples session
two photos side by side of a couple kissing with the boston skyline in the background during their seaport engagement session in boston

Boston Theatre District

Spend a romantic evening in Massachusetts by getting all dressed up and heading to one of the prominent theaters in downtown Boston. Boston is well known for performing arts so catch a musical, straight play, or comedy show while in town. A few of the popular venues include the Shubert Theatre, the Wang Theatre, the Wilbur, and Citizens Bank Opera House. You can find a more in-depth guide to the Boston theater scene here.

two photos side by side of a couple holding hands walking with the boston skyline in the background during their seaport engagement session in boston
close up of engaged couple touching foreheads during their seaport engagement session in boston

Drive In Movies Massachusetts

If you are looking for a fun couple activity during the time of COVID, check out one of Massachusetts Drive In Theatres. Choose between driving to Topsfield or Mendon (currently showing Christmas movies) for $30 per vehicle.

artsy black and white photo of a couple kissing with the custom house tower in focus behind them during their boston engagement session
couple kissing with the boston skyline behind them during their classy boston seaport engagement session

Boston Live Music Venues

Home to various music conservatories the talent in Boston is incredibly strong.

Jazz Music- The Beehive

Country Music- Loretta’s Last Call

Indie Bands- Middle East 

Live Music in Cambridge- Sinclair

Alternative Rock Bands- Paradise Rock Club

Shows for touring bigger name acts- Brighton Music Hall or the House of Blues

Music Festivals- Boston Calling or Somerville’s Porchfest (typically takes place in May)

couple arm in arm wearing their college sweaters during their boston seaport engagement session
two photos side by side of engaged couple wearing their college sweaters during their classy seaport engagement session in boston

Boston Date Ideas For The Travel Enthusiast

If you and your date love exploring new cultures or life on the road, then bring a hint of your favorite countries to your next date. No passports required.

If you are craving French culture, then have a picnic at the Crane Estate in the North Shore (it was the backdrop for the Paris scenes in the most recent film adaptation of “Little Women”) while snacking on some macarons from Maca Boston or Finesse Pastries

If you are missing Switzerland then grab your favorite Swiss pastry at Swiss Bakers in Allston.

Craving traditional live Irish music? Then look no further than Cambridge’s Druid.

close up of couple gazing at each other during their fan pier park engagement session
wide shot of couple arm and arm touching foreheads with the boston skyline in the background during their boston seaport couples session

Summer Date Ideas In Boston

Besides the water based date ideas mentioned previously in this article, other fun summer date ideas include Lawn on D, movies at the Hatch Shell, and going to see a free Shakespeare on the Common show.

two photos side by side of a couple dressed up during their boston seaport engagement session
two photos side by side of engaged couple smiling at the camera during their boston seaport engagement session wearing brightly colored hanboks

Boston Fall Date Ideas

The fall season in New England is pretty hard to beat. Spend a day outside amongst the beautiful foliage going apple picking and drinking cider at Carlson Orchards in Harvard or Honey Pot Orchards in Stow.

two photos side by side wearing traditional Korean hanboks during their boston seaport engagement session

Boston Winter Dates Ideas

It’s the most wonderful time of the year to cozy up with someone you love. Aside from snuggling up to watch the classics like “Elf” and “Love Actually” (which you can now see at the Mendon Drive In) here are some other Boston dates ideas for the holidays.

Grab a warm drink and walk around the Christmas tree at the Boston Common, see BLINK at the Faneuil Hall Marketplace (not taking place in 2020), or visit the Seaport’ Christmas tree in all its lights.

Looking to walk around and see holiday lights outside? Then look into La Salette Christmas Celebration.

If you’d like to support a family owned small Christmas tree farm in Stow, MA then head on over to the Mistletoe Christmas Tree Farm to feel like you walked straight into a Hallmark movie.

Starting back up in 2021 you can enjoy ice skating at Boston’s Frog Pond or attend a live show of the Boston Ballet’s Nutcracker ( in 2020 you can watch the show airing on NBC on Nov. 28th). Another fun holiday date idea in Boston is renting an igloo at the Envoy Hotel. These igloos can accommodate up to 6 people and may be reserved for up to two hours.

Looking for a magical drive thru holiday experience? Stay in your car, but still marvel at Christmas lights in Gillette Stadium’s first ever Magic of Lights. “Hosted daily from Nov. 13, 2020 through Jan. 2, 2021. Magic of Lights will run from dusk through 10 p.m. Sunday through Thursday, and from dusk until 11 p.m. on Friday and Saturday.”

If you are looking to head north then drive up to New Hampshire to experience their ice castles. Fun to experience in the day or with their lights at night, this event is a great way to embrace the winter season (it is also an incredible backdrop for engagement photos).

wide shot of couple wearing traditional Korean hanboks during their boston engagement session in the seaport district
two photos side by side of engaged couple smiling at the camera during their boston seaport engagement session wearing brightly colored hanboks

How To Find Cheap Parking In Boston

It constantly blows my mind when someone tells me they have never heard of Spot Hero or Park Wiz. Whether you are visiting Boston for the first time or live downtown with a car you should never be paying the standard garage rates. Anytime I have a shoot or event in the city I am always using Park Wiz to get discounted pricing for the same garage someone would be paying the full price for.

All you do is plug in the address where your date will be and it will show you various options for garages in the surrounding area. Most times I’m spending between $7-$20 max for hours in the city whereas garages can typically charge $20/hour. Plus they usually extend your time for free and give you 24 hours in that garage if you’d like.

If you’d like to try Park Wiz for the first time here is a coupon for $5 off your first parking booking.

silhouette of couple and the boston city skyline during their fall boston seaport engagement session

The couple featured is Sharon & Charlie! For their Boston engagement session we took photos in Beacon Hill, at the Boston Public Garden, and at Boston’s Seaport District. I especially loved photographing their traditional Korean outfits Sharon’s mom bought called hanboks. These two cuties have been together about two years and enjoy taking day trips to coastal towns like Rockport, MA and Kennebunk, Maine. When in the city they enjoy getting sweet dumplings in Chinatown, cocktails at Fort Point’s Drink, and dinner at Committee Boston. I had loads of fun shooting their Boston engagement session and even more fun photographing their November wedding at the Lyman Estate.

If you love a certain Boston date idea listed or feel I missed one let me know in the comments below and if you’d like to book me for a downtown Boston engagement session you can fill out my contact form here.

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