Dating can be hard, and organizing the perfect date can be even harder. But don't worry because we've got you covered! Whether you're looking to get out of your comfort zone with a new date idea, visiting Boston for the weekend with that special someone or exploring the city on your first date, we’ve gathered 57 ideas for your next perfect date!

We've curated ideas:

For the Active Explorer

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  • Go ice skating at the Frog Pond and then walk down Newbury Street and get a hot chocolate at L.A. Burdick Handmade Chocolates. 
  • Grab an ice cream at Sullivan’s and take a walk around Castle Island.  
  • Rent a Blue Bike and ride along the Charles River Esplanade. 
  • Hit the driving range at Granite Links in Quincy, while watching an amazing sunset with a cocktail.   
  • Visit the Kelleher Rose Garden while it blooms in Spring and walk through the Back Bay Fens neighborhood.  
  • Walk through Boston’s Public Garden, all the way to the South End where you will find B+G Oysters. The perfect place to split a dozen oysters, a bottle of wine and an iconic lobster roll.  
  • Ride the Swan Boats in Boston Common. 
  • Pack a picnic and take the ferry out to Spectacle Island. 
  • Get supercharged and go Go Karting in Wilmington.
  • Go on a Boston harbor Whale Watching Tour.  
  • Get lucky at lucky strike and grab a bite while bowling or finding your inner child with their floor of arcade games. 
  • Rent a double Kayak and explore your way down the Charles River.  
  • Take a Haunted Tour in Boston or a pub crawl with The Ghosts of our (Founding) Fathers. 
  • Go star gazing at the Observatory at Boston University.  
  • Check out one of Boston’s popular activity bars.
  • Visit the Charles Hayden Planetarium and experience a planetarium show – with your favorite artist.  
  • Visit the newly opened View Boston at the top of the Prudential Center and curate your itinerary of amazing things to do in Boston during your stay or your next weekend.


For the Foodie

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  • Take a cooking class at Eataly Boston.  
  • Take a tour of Boston’s iconic Sam Adams Brewery in Jamaica Plain, and then grab a flight to share your favorite flavors. 
  • Do a wine tasting at City Winery and check out their bustling performance schedule.  
  • Visit one of Boston’s Food Halls to do a tasting tour and rank your favorites. 
  • Grab Dim Sum or Hotpot in Boston’s Chinatown neighborhood.  
  • Visit one of Boston’s speakeasies and then grab dinner in the neighborhood.   
  • Do a tour of the North End: Grab drinks at one restaurant, dinner at another and end with a cannoli from Modern, Mike’s Pastry and Bova’s.   
  • Go on a food tour!  
  • Dine at Mamma Maria, with great food and a romantic ambiance, it is the perfect choice for your next date night. But you truly can’t go wrong with any of the North End’s restaurants.   
  • Grab a drink and appetizer from one of Boston’s picturesque rooftop bars and restaurants.  
  • Grab dinner and listen to great live music at Darryl’s Corner Bar and Kitchen.  
  • Tour the cheese cave at Formaggio Kitchen in Cambridge.  
  • Grab a doughnut and coffee at one of Boston’s best, Blackbird Doughnuts. Then stroll through the picturesque South End with its parks, brownstones and adorable shops.  

For the Cultural Enthusiast

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  • Grab a latte and breakfast sandwich at Tatte and spend the day exploring the Museum of Fine Arts
  • Watch the Netflix series ‘This is a Robbery: The World’s Biggest Art Heist’, and then visit the Isabella Stewart Gardner to see if you can theorize who did it.  
  • Visit the art at the ICA Watershed and then grab a drink at Downeast Cider House.  
  • Explore Boston’s iconic Boston Public Library, and then book a table at the Courtyard Tea Room for an immersive high tea experience.  
  • Paint pottery at Rainbows Pottery Studio in Beacon Hill or Clayroom in Brookline. Or dive deeper into your creative side, and take a pottery-making class! 
  • Grab dinner and check out a Broadway show with Broadway in Boston.  
  • Create your own scent and make candles with Noted Candles in Allston.  
  • Take in a show and all the laughs at Improv Asylum, before or after dinner in the North End.  
  • Check out all of the comedy show options by checking out Laugh Boston, Improv Boston, Nick’s Comedy Shop, The Wang Theater and more! We recommend drinks at the W Hotel before or after your night of laughter.  
  • Dress to impress and have a night out with the Boston Symphony Orchestra. Grab dinner before in Boston’s South End. MIDA never disappoints.  
  • Grab a table near the stage for The Beehive’s Jazz Brunch.  
  • Jazz Brunch at The Beehive or a drink and jazz show at Wally’s Cafe.
  • Grab dinner in Boston’s South End or Roxbury and catch a show at Boston’s famous Wally’s Café.  
  • Check out this month’s visiting immersive art exhibits at The Castle or one of the pop-up exhibits at one of Boston’s iconic museums.
  • Paint and sip the night away at Muse Paint Bar in Somerville’s Assembly Row. Do this after a few hours of shopping, or before dinner at one of their amazing restaurants.  
  • Get tickets to a candlelight concert in Boston, and then head to dinner.  
  • Visit Time Out Market for your choice of some of Boston’s best vendors and then head to iconic Fenway Park for a game. 
  • Visit The Sports Museum and explore the history of the ‘City of Champions’ and then grab a beer at one of the area’s best sports bars. 
  • Grab a bite to eat at Banner’s Kitchen and Tap, then cheer on either the Boston Celtics or Boston Bruins.  
  • Take a tour of Boston’s historic Fenway Park, and then grab a bite at Tenderoni’s, Eventide, or Hojoko.  
  • Rent a golf suite at Banner’s Kitchen and Tap or Five Iron Golf in Downtown Boston. 


For the Big Spender

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