Dating can be hard. 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 55 ideas for your next perfect date!

We've curated ideas:

For the Foodie

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  • Take a cooking class at Eataly Boston.  
  • Tour Boston's iconic Sam Adams Brewery in Jamaica Plain, then enjoy a flight to share your favorite flavors. 
  • Do a wine tasting at City Winery and check out their bustling performance schedule. 
  • Embark on a food tour in Boston or Cambridge.  
  • Visit one of Boston's Food Halls for a tasting tour and rank your favorites. 
  • Have Dim Sum or Hotpot in Boston's Chinatown neighborhood.  
  • Uncover one of Boston's speakeasies and then grab dinner at a neighborhood spot.  
  • Do a tour of the North End: Start with drinks at one restaurant, dinner at another, and end with a cannoli from Modern, Mike's, or Bova's.
  • Sip a cocktail and take in the view from one of Boston's picturesque rooftop bars and restaurants.  
  • Enjoy mouthwatering Mexican-inspired dishes and Tequila-forward cocktails on the cheap at Bodega Canal's Cheap Date Night Wednesdays.
  • Pair dinner with live music at Darryl's Corner Bar and Kitchen.  
  • Tour the cheese cave at Formaggio Kitchen in Cambridge.  
  • Treat yourself to a doughnut and coffee at Blackbird Doughnuts and stroll through the South End's picturesque parks, brownstones, and adorable shops. 

For the Cultural Enthusiast

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  • Watch the Netflix series "This is a Robbery: The World's Biggest Art Heist," then visit the Isabella Stewart Gardner Museum to see if you can theorize who did it.  
  • Travel to the ICA Watershed to view this season's exhibits and then grab a drink at Downeast Cider House.  
  • Order a latte and breakfast sandwich at Tatte and spend the day exploring the Museum of Fine Arts
  • Explore Boston's iconic Boston Public Library. Afterward, reserve 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! 
  • Score tickets to a Broadway show with Broadway in Boston and enjoy a pre-show dinner in the Theatre District.
  • Create your own candles with Noted Candles in Allston.  
  • Laugh out loud at Improv Asylum before or after dinner in the North End. Want more comedy? Check out Laugh Boston, Improv Boston, Nick's Comedy Shop, and the Wang Theater.
  • Dress to impress for dinner in Boston's South End followed by catching a Boston Symphony Orchestra performance at Symphony Hall. 
  • Secure a table near the stage at The Beehive's Jazz Brunch or a jazz show at Wally's Cafe.
  • Have dinner in Boston's South End or Roxbury and catch a show at Boston's famous Wally's Café.  
  • Check out this month's immersive art exhibits at The Castle or a pop-up exhibit at one of Boston's iconic museums.
  • Paint and sip the night away at Muse Paint Bar in Somerville's Assembly Row after shopping or before dinner at one of their incredible 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. 
  • Explore the history of the "City of Champions" at The Sports Museum and then stop by one of the area's best sports bars
  • 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. 
  • Enjoy a meal at Banner's Kitchen and Tap, then cheer on the Boston Celtics or Boston Bruins.  

 

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. 
  • Cool off with an ice cream from Sullivan’s while walking around Castle Island.
  • Get supercharged and go indoor Go Karting in Wilmington.
  • Rent a Blue Bike and ride along the Charles River Esplanade. 
  • 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 paddle your way down the Charles River.  
  • Hit the driving range at Granite Links in Quincy while watching an amazing sunset with a cocktail.  
  • Visit the Charles Hayden Planetarium and experience a planetarium show – with your favorite artist.  
  • Visit the Kelleher Rose Garden while it blooms in Spring and walk through the Back Bay Fens neighborhood.  
  • Go star gazing at the Observatory at Boston University.  
  • Walk through Boston’s Public Garden 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. 
  • Check out one of Boston's popular activity bars.
  • Pack a picnic and take the ferry out to Spectacle Island. 
  • Go on a Boston harbor Whale Watching Tour.  
  • Take a Haunted Tour in Boston or a pub crawl with The Ghosts of our (Founding) Fathers. 
  • Visit 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 Big Spender

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  • Take a helicopter tour over Boston and Cape Cod with Helicopter Tour Boston.  
  • Book a table at Rare Steakhouse, and then test your luck at the tables at Encore Boston. We recommend asking about the crab legs.
  • Go to one of Boston's most romantic dining experiences.  
  • Start your day with brunch at Paramount before shopping along Charles Street in Beacon Hill.
  • Go shopping along Newbury Street or at the Copley Place Mall. Cap it off with a coffee, tea, or cocktail at Oak Long Bar. We recommend ordering the skillet cookie.
  • Book a spa day at The Spa at Four Seasons HotelMandarin Hotel, or Encore Boston Harbor