The 42 Best Date Ideas in Boston, Massachusetts

Sure, dinner and a movie is fun, but there's so much more to do in Beantown.
Couple sitting in front of Boston skyline at sunset
Photo: Grant Faint / Getty Images
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by
Lindsay Tigar
lindsay tigar the knot
Lindsay Tigar
Wedding Planning Contributor
  • Lindsay contributes articles to The Knot Worldwide, with a specialty in honeymoon travel and creating wedding planning.
  • Lindsay owns a content agency, Tigar Types, to help businesses of all sizes grow their digital footprints.
  • Lindsay freelances for a plethora of publications, covering many topics, ranging from wedding advice and planning to travel, health and more.
Updated Feb 15, 2024

Whether you call Beantown home or visit for a romantic escape, the city offers plenty for every couple and adventure. When planning fun and memorable date ideas in Boston, you have many neighborhoods to choose from, all offering a unique experience. From strolling along the iconic Charles River Esplanade and dining in a quaint restaurant in the historic Beacon Hill area to going on a sunset cruise in the Boston Harbor or grabbing authentic Italian food in the North End. Here, we've rounded up the top-rated date ideas in Boston.

In this article:

Fun Date Ideas in Boston

There's a time for a candlelight dinner—and a time for seeing where your curiosity takes you. These fun ideas create a date you'll giggle about for years.

Paddle Along the River

As you're walking through Boston Public Garden, you might notice very large swans—real ones and also, a swan doubling as a boat. These are inexpensive to rent, powered by one driver who pedals while the others sit and enjoy the ride. One trip around the pond is one-quarter mile and takes about an hour. It's a fun date idea to see the oldest public park in America while you're touring Boston.

Cost: Affordable. Tickets: $4.50 for Adults; $4 for Seniors (age 65+)

4 Charles St, Boston, MA 02116

Visit the Red Sox

If you don't happen to be visiting Boston during baseball season, don't worry—you can still tour the legendary Fenway Park, which the Red Sox call home. Here, you climb to the top of the 37-foot 'Green Monster' to see a gorgeous view of the stadium and the surrounding city. Considering Fenway is often titled 'America's Most Beloved Ballpark,' you can guarantee this will be a fun date idea.

Cost: Ticket prices vary (Adult tickets: $25 for the in-person tour)

4 Jersey St, Boston, MA

Go Island Hopping

While island hopping in the Northeast isn't quite like the Caribbean or Greece, Boston Harbor Islands are still worth the trek. You can take a ferry out of the city to see the 34 islands and peninsulas that make up Boston Harbor Islands National and State Park. While you're here, there are plenty of fun date ideas to try out, from simply exploring to hiking, picnicking, riding bikes and more.

Cost: Ferry prices vary. Check the official website for details.

191W Atlantic Ave, Boston, MA

Fulfill Your Chocolate Craving

Not all fun date ideas in Boston must be adventurous—come some be indulgent. For those duos with a sweet tooth, you can immerse yourself in a tasty experience with a tour of the Taza Chocolate Factory in Somerville. This tour includes a brief talk about their history, sourcing methods, how cocoa is grown and processed, a sneak peek into the manufacturing and a taste of lots of chocolate along the way. Is your mouth watering yet?

Cost: $12 per person; Online reservations are required

561 Windsor St, Somerville, MA

Play Ping-Pong

Dinner dates can be sultry, but some friendly competition can also make you feel bonded and attracted to your partner. A unique and fun date night idea is to try your luck at ping-pong by visiting SPIN social club in the Seaport. You pay $49 for an hour of endless play, and then you can extend your date to chit-chat and drinks by visiting their full-service bar and restaurant.

Cost: $49/hour of ping-pong

30 Melcher St, Boston MA

First Date Ideas in Boston

There's something magical, nerve-wracking and thrilling about meeting someone new. You want this initial get-together to be memorable since, hey, it may be your last first date ever. Here, our top picks for first-date ideas in Boston:

Eat Your Way Around the World

One of the hardest parts of planning a first date in Boston (or in any city) is figuring out the right type of cuisine based on preferences, dietary restrictions and, well, vibe. Luckily, a visit to Time Out Market Boston allows you to pick and sample from 15 kitchens with different cuisines. In addition to this plethora of food choices, there are two large bars with an expertly curated cocktail list and an all-local beer list. Check the programming schedule to see if events are happening when you visit!

401 Park Dr, Boston, MA

Take a Trip to Italy

Nothing can hold a candle to the North End if you can't get enough of pizza, pasta and any other Italian food you can feast on. This food tour lets you bring your first date on a culinary adventure, sampling Italian delicacies and desserts. This highly-rated experience allows you to connect over a shared love of food while experiencing the oldest neighborhood in Boston through the eyes of a lifelong resident. Psst: spoiler–you'll nibble on everything from wood-fired pizza and a cold-cut sandwich to an award-winning Salumeria.

Cost: Ticket prices vary.

Paint Something Pretty

For those up for a short drive out of the Boston city proper, this first date idea allows you to delve into your creative side at The Paint Bar. While following along with the instructor, you and your date will learn something new and sip on your beverage of choice. As a bonus, they also offer a variety of paint tutorials and kits for a date night at home.

Cost: Kits/tutorials are $25+

955 Watertown St, Newton, MA

Grab a Coffee & Stroll

There are plenty of ways to connect when you're on a first date in Boston. Over drinks, through a yummy dinner and hopefully, plenty of conversation. For a more casual approach that involves more chit-chatting than participating in an activity, consider grabbing a coffee and taking a stroll through Harvard Square as you explore the historic Harvard Yard. It's charming, cost-effective and ideal for bookworms and movie buffs who have seen this famous area in Cambridge portrayed on the big screen or in a best-seller.

Cost: Free

18 Brattle St Ste 352, Cambridge, MA

Quack Your Way to Love

Though locals may find it cheesy, if you haven't experienced the infamous Boston Duck Tours, it's definitely worth testing it out for a first-date idea. This vehicle is 'amphibious' since it can easily go from land to water. That's right, as you listen to your (hilarious) tour guide, you will drive through the streets of Boston, and then your ride turns into a boat to see more of the city from the river. Choose from three departure locations: the Prudential Center, the Museum of Science and the New England Aquarium.

Cost: Ticket prices vary (Adult tickets: $52.99 per person)

Locations: Prudential Center - 53 Huntington Ave, Boston, MA; Museum of Science - 1 Science Park, Boston, MA; New England Aquarium - Central Wharf, Boston, MA

Free and Cheap Date Ideas in Boston

Not all date ideas have to be expensive or elaborate to be memorable. In fact, Boston offers countless free or cheap date options for every type of dynamic duo.

Sip For Free

If your budget is tight but your thirst is high, consider stopping by The Urban Grape with your love on Thursday at 5 p.m., when they host free wine tastings. The Urban Grape is America's largest certified Black-owned beverage retailer and thoughtfully curates wine, beer and spirits with an emphasis on the representation of diverse makers, regions and varietals. Grab a selfie in front of their Instagrammable art installation featuring over 800 bottles from 25 countries.

Cost: Free to taste

303 Columbus Ave, Boston, MA

Stroll Through History

For a budget-friendly day out, check the weather forecast for a sunshine-y day, and stroll over to Boston Common, the oldest park in the country. You can pack a picnic from nibbles you already have at home or pack a mug of coffee. Even coming empty-handed and walking hand-in-hand is a sweet way to pass an afternoon without breaking the bank.

Cost: Free

139 Tremont St, Boston, MA

Go For a Walk Through History

There are some days when you want to spend time with your partner, but you are feeling the pinch of shelling out $100 for yet another dinner out. Save your cash but enjoy quality time by walking Boston's Freedom Trail. This 2.5-mile path takes you through 16 historically significant sites in Boston, beginning in downtown Boston and finishing at the Bunker Monument in Charlestown. You'll pass by notable stops like Faneuil Hall, the Paul Revere House and the USS Constitution frigate, to name a few.

Cost: Free, optional guided tours may have fees.

139 Tremont St, Boston, MA

Stop and Smell the Roses

For another outdoor adventure that's a little less city and more nature-focused, consider a day trip to the Arnold Arboretum in Jamaica Plain. Accessible via public transport, this is a free and beautiful outdoor space with various plant collections. This is the oldest conservatory in the country, featuring 265 breathtaking acres of shrubs, flowers, trees and vines. Check out their website to see about special events and happenings.

Cost: Free

125 Arborway Jamaica Plain, Boston, MA

Chit-Chat About Art

Even if you can't quite afford a one-of-a-kind masterpiece, you can admire iconic works of art! For a fun and cheap date idea in Boston, take a self-guided public art walk in the Seaport District to discover unique sculptures and installations. Technically called New Bedford's Seaport Art Walk, it is the city's first large format outdoor public art installation that changes each year. This date idea is best for July to October to avoid Boston's difficult winners.

Cost: Free

Atlantic Ave &, Seaport Blvd, Boston, MA

Unique Date Ideas in Boston

Step outside of the box—and perhaps your comfort zone—by booking one of these unique date ideas in Boston. '

BYOP

And by BYOP, we mean… bring your own pup! For couples who love their doggo almost as much as they love one another, plan a date to Park-9, New England's first indoor dog park and bar, featuring 10,000 square feet of multiple indoor on- and off-leash areas. While your furry pal is running off energy, you can order a beer (or two) and sit at their bar or in the comfortable lounge area.

Cost: Day pass or membership required for entry; dogs must be registered before entry

48 Waters Ave #1, Everett, MA

Escape the Room

Some friendly competition is good for your relationship—and so is teamwork. Escape the Room Boston helps you work together to, well, escape a room. This unique and interactive date is an unconventional twist on a live-action video game. As you go through the timed-experience, you can unlock clues and hidden messages to find your way out, ASAP.

Cost: Tickets $37+

33 West St, 3rd Floor, Boston, MA

Bike Around Town

Upgrade to two wheels instead of walking like you always do as a city dweller! For a unique and fun date idea in Boston, consider renting bikes from the Hubway Bike Share. Metro-Boston's bike-sharing system provides more than 1,300 bikes at 140 stations throughout the cities of Boston, Cambridge, Somerville and Brookline. By allowing you to move faster, you can plan a date where you visit landmarks, shops, parks, restaurants and cafes throughout the city—and maybe even switch to a membership if you call Beantown home.

Cost: Local residents can become Annual or Monthly members, and visitors can choose a 24-hour access pass ($6) or 72-hour pass ($12) or even the Monthly option ($20) for extended stays.

Laugh and Love

The Improv Asylum is a must-see unique date idea for comedy lovers in Boston. It's a comedy club that started more than 25 years ago in the North End neighborhood of the city. They run performances seven days a week, so snag a time that works for you and enjoy the show!

Cost: Ticket prices vary, $5+

216 Hanover St, Boston, MA

Geek Out

Fans of innovation, science and technology will have their minds blown during a unique date exploring the MIT Museum. It's in the heart of Cambridge on the Massachusetts Institute of Technology's campus and provides fascinating exhibits in these game-changing industries. We suggest booking an early dinner or having a drink after your visit to discuss what you learned—and how inspired you feel to make moves.

Cost: Admission fees apply (Adult tickets: $18 per person)

Gambrill Center, 314 Main St, Cambridge, MA

Hear the Tea

You probably remember bits and pieces about the historic Boston Tea Park that sparked the American Revolution. But what about experiencing it—sort of—firsthand? For a unique date idea, consider visiting the Boston Tea Party Ships and Museum, where you'll hear from historical interpreters, explore interactive exhibits and artifacts, and step on board the full-scale replica 18th-century sailing vessels. And yes, you do get to pour some tea into the harbor.

Cost: Admission fees apply. Tickets $34+ per person

306 Congress St, Boston, MA

Winter Date Ideas in Boston

The weather outside in the winter in Boston is definitely frightful, yet these winter date ideas will warm you up fast. Snuggle up!

Go Ice Skating

Pile on the layers and lace up your skates under a winter wonderland at Boston Commons Frog Pond. This outdoor skating rink is a must-experience for locals and tourists who want to spark romance in the chilly air. After you do a few laps and snag a photo, head to a nearby bar or restaurant in Beacon Hill or Backbay for a nightcap.

Cost: Admission $10 for adults; skate rentals $15 for adults

38 Beacon St, Boston, MA

Browse the Holiday Market

If you're in the area in the holiday season or just looking for a seasonal idea, you must experience the festive atmosphere at Boston Winter Market. Located near City Hall, this annual event features a holiday market and seasonal attractions. Might we suggest hot chocolate and a gooey grilled cheese sandwich?

Cost: Free to enter; expenses vary based on purchases.

1 City Hall Square, Boston, MA

Try Snowshoeing

A short drive from the heart of Boston, one winter-inspired date idea is going snowshoeing at Blue Hills Reservation. This area in Milton, MA, offers prospective hikers, wanderers and snowshoers more than 7,000 acres of winter playground with about 125 miles of trails to explore. The only catch is you'll need to bring your own equipment, so come prepared.

Cost: Free. Bring your own equipment.

695 Hillside St, Milton, MA

Hot Chocolate Tasting Tour

There are hot tea drinkers and coffee addicts—and then there are those who countdown until the darkest day of winter when they can sip on a perfect, rich hot chocolate. But why settle on one cup when you can have…. all you can drink? Take yourself (and your partner, of course) on a self-guided tour of the top-rated hot chocolate spots in Boston, from L.A. Burdick Handmade Chocolates to Beacon Hill Chocolate and more.

Cost: Expenses vary based on purchases.

Lights, Action, Tree!

For a winter date idea that's equal parts romantic and holiday festive, grab your date and attend the annual Boston Common Tree Lighting Ceremony. The official holiday season kick-off in Boston includes the lighting of the City of Boston's official Christmas tree and other trees throughout Boston Common and the Public Garden. Make sure to book a dinner reservation following the fun to extend the evening celebration.

Cost: Free

139 Tremont Street, Boston, MA

Spring Date Ideas in Boston

After a very long winter of dark and cold days, spring means the city comes alive again. These date ideas are colorful and cheerful, just like Boston's mood during this season.

Attend Opening Day

Celebrate the start of spring with your one-and-only by attending the opening day of the Boston Public Garden Swan Boats. This date varies every year, but this year will take place on Saturday, April 13th, 2024. We recommend dressing for the occasion so you can snap a photo for social media.

Cost: Affordable. Tickets: $4.50 for Adults; $4.00 for Seniors (age 65+)

4 Charles St, Boston, MA 02116

Be Amongst the Flowers

Every May, the Arnold Arboretum celebrates when its lilacs are in full bloom, creating a picture-perfect backdrop for photos and picnics. Called 'Lilac Sunday', this event will take place on May 12 this year, from 10 a.m. to 3 p.m. Not only is this free, but it's the only day of the year you are permitted to bring a picnic and enjoy more than 400 beautiful flowers.

Cost: Free

125 Arborway, Boston, MA

Cheer Your Heart Out

Did you know that most businesses in Boston give their employees Marathon Monday off every year so they can cheer for runners at the Boston Marathon? It's a city-wide celebration and time-honored event that makes for a sweet and heart-pumping spring date idea. This year, the marathon takes place on Monday, April 15, but it changes each year. Don't forget to make signs and book a spot for a celebratory beverage.

Cost: Free to spectate

Get a Bird's Eye View

For an active spring date idea in Boston, take a day trip to Spectacle Island, part of the Boston Harbor Islands. The name comes from its shape since it resembles a pair of spectacles. In addition to offering a gorgeous skyline view, Spectacle Island has a diverse history, including periods of use as a farming community, a quarantine station for smallpox patients and a landfill. Today, you can explore hiking trails or engage in various outdoor activities and stop by the visitor center with exhibits about its history and ecosystem.

Cost: Ferry prices vary.

Sing Your Heart Out

Music can put us in all sorts of moods—and help us feel connected to our partner. For a weekend-long date idea in the spring, attend the Boston Calling Music Festival, a multi-day event featuring live music performances. This three-day, four-stage concert usually has an impressive line-up of artists and a plethora of food options. This means you get to enjoy good jams and good eats—what's not to love?

Cost: Ticket prices vary. General admission 1-day tickets starting at $189 per person

Harvard Stadium, Boston, Massachusetts

Summer Date Ideas in Boston

While many locals flee the city during the sticky days of summer, there's plenty to do during this season in Boston. Here, a few flirty and fun ideas.

Dine Al Fresco

With 1,000 square feet of outdoor dining, LoLa 42 boasts one of the largest outdoor patios in Boston's Seaport neighborhood—and offers an attractive nightlife scene with delicious plates of sushi, globally-inspired dishes and craft cocktails. Here, you can eat your way through a global menu inspired by the countries on the 42nd parallel, including Japan, Portugal, Spain and more.

22 Liberty Drive, Boston, MA

Boston Harborwalk

While the humidity in Boston during the summer isn't to be discounted, there's no better way to escape the heat than walking by the water. We recommend grabbing your partner and going for a leisurely stroll along the Boston Harborwalk, a scenic path that offers views of the waterfront and city skyline. This path is actually a 43-mile linear park along Boston's shoreline, connecting Boston's waterfront neighborhoods to Boston Harbor and each other. We suggest walking a bit until you're sweaty—and then finding a cold beverage to cool down.

Cost: Free

Harborwalk, Boston, MA

Witness Shakespeare

Just like Central Park in New York City, Boston also has its own Shakespeare in the Park in Boston Common. Throughout the summer, stop by for a free show written by one of the most well-known poets in history. It's romantic, simple and a way to enjoy the star-speckled summer sky and fresh air.

Cost: Free

139 Tremont St, Boston, MA

Go Kayaking

Layer sunscreen and wear your swimsuit to experience Boston via the Charles River. Start your summer day date by renting kayaks at many spots throughout the area, and keep paddling until you're ready for lunch. It may be hot, but it's also a refreshing way to be a tourist.

Cost: Rental fees apply, rentals $30+

See the Stars

And by stars, we mean superstars! For a fun—and air-conditioned—date idea, attend a live concert or event at TD Garden, a major entertainment venue in Boston. Upcoming events in 2024 include Disney on Ice, Olivia Rodrigo and Janet Jackson.

Cost: Ticket prices vary.

100 Legends Way, Boston, MA

Go Cruising

Step aboard a romantic sunset cruise in Boston for a summer date idea in Boston Harbor. You'll enjoy the gorgeous skyline, pass by the USS Constitution, with its evening cannon firing, the Old North Church and Historic Site and the Charlestown Navy Yard—to name a few. And if you want, you can purchase drinks and snacks while on board.

Cost: Cruise prices vary, tickets $48+ per adult

60 Rowes Wharf, Boston, MA

Fall Date Ideas in Boston

For many people, fall is the best season of all, with more bearable weather and the unbelievable colors of the New England trees. The best Boston fall date ideas include:

Go Apple Picking

Experience the quintessential fall activity via a day of apple picking at Russell Orchards in Ipswich, a short 15-minute drive from the heart of Boston. You will feel far away from the hustle, though, with picturesque orchards surrounded by the vibrant colors of Autumn. After picking apples, take your bounty home and cook up apple desserts to continue the seasonal fun.

Cost: Varies

147 Argilla Rd, Ipswich, MA

Go On a Witch Hunt

Though you'll have to be up for battling massive crowds, if you're up for elbowing, a can't-miss fall activity is Salem's Haunted Happenings from October 1 through 31. Located where the infamous Salem Witch Trials happened hundreds of years ago, this town can be accessed via public transport. Events include a Grand Parade, the Haunted Biz Baz Street Fair, Family Film Nights, costume balls, ghost tours, haunted houses, live music and chilling theatrical presentations.

Cost: Free to enter; expenses vary based on purchases.

Starting Point: Salem Regional Visitor Center, 2 New Liberty Street, Salem, MA

Bottoms Up

Fans of pumpkin beer will love Harpoon Brewery's Oktoberfest with live music, beer tastings and festive activities. Flowing taps, live oompah music, stein-hoisting competitions, pretzel-eating contests, chicken dancing and more will be waiting for you at our largest festival of the year. Raise a stein with us under our open air tents with thousands of beer lovers!

Cost: Ticketed event

306 Northern Avenue, Boston, MA

Boston Book Festival

Every fall, literary enthusiasts unite at the annual Boston Book Festival to celebrate and debate words and ideas. You and your book-loving partner will engage with renowned authors as they share insights during captivating talks. After turning on your brain, put on your walking shoes to explore the vibrant street fair. Attending is free, making it an inclusive and inspiring experience for avid readers and casual visitors alike.

Cost: Free to attend.

Copley Square, Boston, MA

Fall Foliage Road Trip

Embark on a picturesque road trip to witness the spectacle of fall foliage from the Berkshires to the White Mountains, depending on how long you want to drive. As you navigate scenic routes, you and your partner will be in awe of the vibrant canvas of autumn hues, with leaves ablaze in shades of red, orange and gold. The best part about this fall date is it's completely customizable—you can simply drive or access hiking trails. No matter what you do, it'll be an unforgettable adventure.

Cost: Gas and potential park fees.

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