You’d think that once you’ve been bitten by the love bug or shot by Cupid’s arrow that a manual of Boston date ideas would fall magically from the sky–but alas, it does not.
That kind of knowledge only comes with experience, a little inside knowledge, a few horror stories of what not to do and a little trial and error. And if you haven’t got there yet, we’ve got your back.
Nobody needs to know about your frantic Googling for date ideas in Boston except us and you, so let’s make a deal. We’ll supply you with some fun, cute, romantic and even a few cheap date ideas, and you focus on being a great person to go on a date with!
Whether you’re looking for ideas for a first date or hatching plans for a cute date night with your long term partner, we’ve covered all the bases we can think of. Read on to find out what your plans are about to look like…
And just so you know, nobody pays us to be listed here. They’re just places we’ve been or experiences we’ve had that we want to recommend to you, so you can find the best things to do in Boston. No affiliate links!
Best Date Ideas in Boston
Track Down Boston’s Secrets on a Scavenger Hunt
Location: 📍Various
First up on our list of the best date ideas in Boston, a challenge to test your relationship’s teamwork skills!
You don’t have to be a fan of history or competitive games to play, but if you are, then you’ll love these scavenger hunts.
Uncover hidden gems and quirky trivia as you race to solve clues sent straight to your phones. Perfect for outdoorsy couples who love a bit of mystery and adventure, you'll explore Boston’s historical and cultural landmarks in a fun, interactive way and hey, they’re super fun, interesting, healthy, and sooo easy to organize.
Practical information: Prices start at around $15 per person. Hunts are available year-round and you can stop and start the game whenever it’s convenient for you.
Stroll Through the Public Garden
Location: 📍Boston Public Garden
Looking for Boston date ideas that are low-key but also romantic? Well, that’s a walk in the park. Almost literally.
Take a romantic walk in Boston’s most picturesque park, AKA Boston Public Garden. There’s a little something for everyone here: beautiful flower beds, charming footbridges, a serene lagoon that looks straight out of a fairytale.
Practical information: Open daily from dawn to dusk, and it’s free to enter.
Hang Out On The Common
Location: 📍Boston Common
I think if you asked Boston’s population what they did for their first dates, this would be up there in the top 5. Why? It’s super easy to organize, not stressful at all, and it emphasizes the most important part of a first date: getting to know your partner.
The message is this: don’t overcomplicate things. Grab some takeout and have an impromptu picnic on Boston’s historic Common, or grab coffees to go and sit yourselves down and talk. If you run out of things to say, this is a great place to do some people-watching, or you can explore the paths, enjoy the greenery and just enjoy hanging out together.
Practical information: Open daily; no admission fee. Food trucks often pop up for quick bites.
Pick Players 1 and 2 at an Arcade
Location: 📍Various
You don’t have to be a gamer to know that every player one needs their player two, even for non co-op games (you know, when you just need some reassurance that you did press the button and therefore shouldn’t have lost!).
There are a few places you can game it out in and around Boston:
- 📍Versus (DTX): Cover charge is $5 for unlimited gaming (arcade games and screens).
- 📍Roxy’s (Cambridge): Kind of a speakeasy vibe (you enter through the freezer). Awesome cocktails and the pinball machines are 🔥
- 📍BitBar (Salem): Yeah, it’s a road trip to get here but the retro games are incredible (Sega Dreamcast and occasional Smash tournaments).
Practical information: 21+ to enter, hours vary by location, with most open late into the evening. Entry fees range from $5-$10, depending on the venue.
Fun Boston Date Ideas
Check Out Boston’s Museums Together
Yeah, yeah, you’re gonna say you’ve already been to all of these (or you have no interest in going, if you’re a tourist).
Well, you’re wrong to strike visiting museums off your list of fun Boston date ideas. Firstly, there’s tons of stuff tucked away in these places, so even if you or your date have visited before, there’s almost no way you’ve seen everything.
Second of all, you might not have been together, which is sort of the point of a date. I can only speak for myself, but my partner and I have the best time walking around museums - big and small, famous and unknown - they’re great for discovering new things together and if the weather’s bad, you’re nice and warm inside, or if it’s hot, make the most of that sweet AC.
Here’s where I recommend:
- 📍Isabella Stewart Gardner Museum:
A Boston classic but so worth it. Built in a Venetian-style, this palace is filled with art, rare books, and beautiful gardens. Perfect if you or you or date is into art. - 📍Museum of Fine Arts
Speaking of art, this place has centuries of art from all around the world. Whether you’re into ancient artifacts, contemporary masterpieces, or somewhere in between, there’s something to capture your imagination. - 📍Boston Tea Party Ships and Museum
Well, this is Boston, after all. Relive the night that sparked a revolution at the Boston Tea Party Ships and Museum. And, if nothing else, you can actually toss tea into the harbor and explore replica ships. - 📍Harvard Museum of Natural History
Take my advice and go here on a Sunday morning (it’s free). It’s home to an absolutely stunning glass flower exhibit. - 📍Boston Fire Museum
A cool way to discover Boston’s history through a lens many of us don’t think about anymore. It’s free which is a bonus (donate, if you can) and there’s loads of cool artifacts inside.
Visit Franklin Park Zoo
Location: 📍1 Franklin Park Road, Boston
Take a walk on the wild side at the Franklin Park Zoo.
With over 100 species to see, including lions, gorillas, and giraffes, it’s a fun and adventurous date that brings out your inner kid. It’s also super easy to get here using public transportation so could be a good call if you’re visiting or want to leave your car at home.
Oh, and if you’re visiting during winter–check out the Boston Lights Experience!
Practical information: Open daily, with adult tickets priced at $19.95. Discounts are available online.
Go Ice Skating on Frog Pond
Location: 📍Boston Common Frog Pond
Speaking of winter, Boston winters aren’t quite like any other. Of course it gets cold in other places, but that winter chill really seeps under your skin and right through your bones.
Be that as it may, when in Boston, do as the Bostonians do: lace up your skates and glide hand-in-hand on Frog Pond. This quintessential winter date is both fun and romantic, and it’s a great photo opportunity since you have the Boston skyline as your backdrop. Warm up afterward with hot chocolate from the nearby snack stand.
Practical information: Open seasonally from November to March. Admission is $6 for adults, with skate rentals available for $12.
Do a Tour of Boston Public Library
Location: 📍700 Boylston Street, Boston
Looking for unique Boston date ideas? This is it; there’s only one Boston Public Library, after all.
If you haven’t heard of or seen pics of Boston Public Library before, I’m guessing you haven’t played Fallout 4 before (ask your gamer partner about it, they sure have). Aside from being featured in a popular gaming franchise though, Boston Public Library is the 3rd biggest library in the US and, let me tell you, incredible to look at.
Words just won’t do the beauty of this place justice so I’ll just leave you with some facts that’ll appeal to any fellow book lovers: this was the first public library in the US, first to have a children’s room and first to have a branch library.
Practical information: Free guided tours are available, with no admission fee. The library is open daily.
Go Bowling at Kings Dining & Entertainment
Location: 📍Various
If you’re looking for fun date ideas in Boston, bowling has got to be up there.
Combine dinner, drinks, and a little friendly competition with a night of bowling at Kings. With everything you need under one roof (entertainment, great food and drink, and a playful, buzzing atmosphere), King’s is a super safe bet to have a great date.
PSST: If you or your partner is vegetarian, good news! The impossible burgers here are great🤤
Practical information: Open daily, with lane rentals starting around $25 per hour. Reservations recommended.
Do a Cambridge Brewery Tour
Location: Various breweries in Cambridge
Back in the early 1900s, Boston was a beer-brewing powerhouse. Of course, the Prohibition era put a swift end to all that, but as soon as alcohol was back on the legal menu, Boston bounced back better than ever.
These days, you’ll find some of the top breweries in the Boston area around Cambridge, so if you and your partner like a hops based beverage, I’d recommend you “hop” on over to somewhere like 📍Cambridge Brewing Company or 📍Lamplighter Brewing Co.
Sample local craft beers, learn about the brewing process, and enjoy the relaxed atmosphere (all in the name of science, if anybody asks!).
Practical information: Tours typically run on weekends. Prices vary, but some are free with beer purchases.
Movie Night at Coolidge Corner Theater
Location: 📍290 Harvard Street, Brookline
Cozy up in this historic theater to catch an indie flick, cult classic, or the latest arthouse film. The Coolidge Corner Theatre’s vintage charm and unique movie selection make it an ideal spot for movie-loving couples.
And, let’s be real, it’s a step above just inviting someone over for a movie at your place.
Practical information: Ticket prices range from $13.50 to $17.00, depending on the show.
See a Game at Fenway Park
Location: 📍4 Jersey Street, Boston
In case you haven’t heard (somehow), Boston is home to the Red Sox and yes, that’s a very big deal.
If you’re both baseball fans, you probably don’t need me to suggest cheering on the Red Sox at the historic Fenway Park. But even if you’re not a die-hard baseball fan, the electric atmosphere and shared excitement make for a thrilling date.
Plus, there’s nothing quite like bonding over a Fenway Frank.
Practical information: Games run from April through October. Ticket prices vary widely, starting around $30.
Romantic and Cute Boston Date Ideas
Visit the Arnold Arboretum
Location: 📍125 Arborway, Boston
Wander through 281 acres of meticulously curated trees, plants, and flowers at the Arnold Arboretum.
Apart from being absolutely gorgeous in all seasons, the Arboretum is an amazing place to take your date to go for a long walk, look at beautiful plants and escape the urban jungle for a little while.
That’s not to say this place doesn’t get busy – it sure does – but if you’re willing to stray off the main paths and do a little exploring of your own, it’s easy to immerse yourselves in a hand-in-hand adventure of your own.
Practical information: Open daily from sunrise to sunset. Free admission.
Attend Jazz Night at Wally's Cafe
Location: 📍427 Massachusetts Avenue, Boston
Looking for romantic date ideas in Boston that don’t break the bank? Check out Wally’s cafe.
As the oldest family-owned and operated jazz club in Boston, Wally’s is a local favorite and pretty much a landmark in the Boston music scene. They’ve been hosting live music since 1947, and to this very day I’d say the atmosphere here is pretty much unmatched.
Many of the musicians are local or students, there’s nothing pretentious or fancy-shmancy, just expect a night of smooth tunes, talented musicians, and an intimate atmosphere that’s perfect for a romantic evening.
Practical information: 21+ only. Shows are nightly, with no cover charge, though tips for musicians are encouraged.
Go for a Swan Boat Ride
Location: 📍Boston Public Garden Lagoon
Hey, you wanted romantic date ideas, that’s exactly what you’re gonna get.
You’ve probably seen swan boats in movies, even if you’ve never set foot in one before, and yes, they’re just as slow and serene-looking as the creatures they’re modeled after.
Are they a bit old-fashioned, and whimsical? Sure they are, but that’s what makes them charming! For over 145 years, these boats have been a part of the Boston scene and it’s absolutely worth doing at least once!
Oh and don’t worry, you won’t be in charge of pedaling. Just sit back, relax, and enjoy the trip around the lagoon.
Practical information: Rides operate from April to September, with tickets priced around $4.50 for adults.
Kayak or Paddle Around the Charles River Esplanade
Location: 📍Charles River
If you and your partner are outdoorsy, sporty types, you’ll wanna check this out.
Ask any Bostonian where their favorite views are, they’ll more than likely tell you it’s at the Charles River Esplanade. The sunset views over the river are a must-see (seriously, it’s so peaceful and beautiful) and it’s a great area for exploring on the water.
If you’re looking for something more activity-based, pick up some rental kayaks or paddleboards and splash your way to romance!
Practical information: The esplanade is free to explore. Kayak rentals start at $32 per hour.
Check Out the Marine Life at New England Aquarium
Location: 📍1 Central Wharf, Boston
Maybe it was an overexposure to the movie The Little Mermaid as a kid, but I’ve always found the ocean a super romantic (if slightly terrifying) place.
If you or your partner shares my aquatic obsession, then I suggest checking out the New England Aquarium. What’s inside? Tons. From playful penguins to majestic sea turtles, there’s plenty to see and learn together – and I really recommend taking a look at the whale watching tour
Practical information: Open daily, with adult tickets priced at $34.95.
Explore the Boston Harbor Islands
Location: 📍Boston Harbor Islands
Looking for cute date ideas in Boston with a hint of an adventure? Time to hit up the islands!
Escape the city with a ferry ride to the Boston Harbor Islands.
Spend the day hiking, picnicking, and exploring, or take a tour of one of the historic forts. It’s so much prettier than you’d expect it to be, but bring food - you can get snacks and stuff out there but you’ll be walking around a lot so, be prepared!
Practical information: Ferries run from May to October, with round-trip tickets costing around $20.
Hit Up Boston’s Best Markets Together
Location: 📍Various locations
Is finding bargains a love language? Asking for a friend.
Explore Boston’s vibrant markets for a date filled with delicious food, unique finds, and local culture. Which markets should you visit? Well that depends on what you want:
📍The Boston Public Market offers everything from fresh produce to gourmet treats, whereas 📍Sowa Vintage Market is perfect for treasure hunting, while 📍Bow Market in Somerville offers a mix of food, drink, and artisan goods.
Practical information: Markets are typically open year-round, with varying hours. Free to enter; bring cash for purchases.
Enjoy a Romantic North End Dinner Together
Location: North End, Boston
We’ve given you loads of Boston date ideas here that aren’t dinner, but dinnertime will come whether we like it or not. And as you’re out on a date, it’d almost be rude not to include some recommendations here.
When it comes to romantic cuisine–if that’s even a thing–, your options are endless. But for me, it’s all about Italian food, and the best place to eat it in Boston is in the historic North End.
Expect authentic Italian cuisine like fresh pasta or cannoli to share in a cozy, candle-lit restaurant…bliss!
Practical information: Reservations are recommended, especially on weekends. Expect to spend $30-$50 per person (+ gratuity).
Find More Things to Do in Boston with CityDays
So there you have it, 28+ date ideas in Boston!
Hopefully, we’ve been able to satisfy your curiosity for now - but you know, there’s always more out there you can discover about Boston.
Discover Boston’s secret sights and noteworthy nooks by playing one of our Boston walking tours, scavenger hunts and outdoor escape rooms!
All you have to do is team up with your partner, friends, family or whoever to solve riddles, complete challenges and answer trivia to lead you on an unforgettable journey around Boston’s most intriguing streets.
The best part? We’ll recommend top-rated bars and cafés along the way and give your team the chance to earn rewards by competing on our leaderboard!
CityDays gives you total freedom to start and finish whenever you like, take extra breaks if you want or need them, and it’s suitable for people of all ages.
You’re also guaranteed your money back if you don’t have an incredible time - although our previous reviews speak for themselves: we’re rated 5/5 on TripAdvisor and 4.95/5 on Google Reviews!