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Isabella Stewart Gardner Museum, Things to Do, Boston
Photograph: Courtesy Isabella Stewart Gardner Museum/Siena ScarffIsabella Stewart Gardner Museum

10 best cheap date ideas in Boston

Win them over with these affordable but thoughtful outings

JQ Louise
Olivia Vanni
Edited by
JQ Louise
Written by
Olivia Vanni

Dating in Boston will usually hit the wallet pretty hard. Paying for pricey nights out and regular date nights can add up if you’re not careful. However, despite Boston’s expensive reputation, there are plenty of affordable options out there as well—you just need to know where to look. We’ve compiled a list of cheap date ideas that are thoughtful, romantic and all cost less than $30. But if you are looking to splurge be sure to check out our list of the most romantic restaurants and most romantic bars in Boston. And if you’re seeing someone for the very first time, peruse our suggestions for the best first date spots

RECOMMENDED: Guide to the best restaurants in Boston

Cheap date ideas in Boston

  • 5 out of 5 stars
  • Museums
  • Art and design
  • Mission Hill
  • Recommended

The best time to visit the stunning Isabella Stewart Gardner Museum is on the first Thursday of the month if you are looking to save a buck. Every first Thursday is free and the museum is open late, so it is just the place to soak up some culture and enjoy the beautiful palace museum. To get the free entry arrive after 3pm on the first Thursday of the month.

  • Shopping
  • Chocolate and candy
  • Somerville
  • price 1 of 4

Why simply buy your date a box of chocolates when you can go on a cocoa-filled excursion together? Somerville is home to Taza Chocolate, and the local brand opens its factory doors to guests Wednesday through Sunday each week. Reserve tickets for a tour—they’re only $12 a pop—so you and that special something can see how this stone-ground treat is made firsthand. Bonus: These tours include a chocolate tasting, so you can finish your date literally on a sweet note.


Located on the busy outskirts of Cambridge, this reservation offers a serene—and completely free—environment for a day date. Take a leisurely stroll around the reservoir, either solo or with your canine companions (there’s a little pond where dogs are allowed to swim and frolic through the water). In the winter, you can warm up after your walk with a coffee, tea or hot chocolate from the nearby La Saison Bakery (add on a pastry, if your wallet allows). During the warmer months, you can always pick up some cheese, crackers and charcuterie down the street at Formaggio Kitchen, and make a romantic outdoor picnic out of your Fresh Pond outing. 

  • Dance
  • Central Sq

Wow your date with some salsa dancing, even if you don’t know how. Havana Club in Cambridge is one of the best spots to bust out those salsa, bachata and merengue moves, no matter how good of a dancer you are. This place kicks off each night with dance lessons for beginners, letting novices stick around and test out their newly formed skills for the rest of the night as everyone else joins. It costs $15 per person for this crash dance class and the following party—both a bargain and the perfect excuse to get closer to your date.

Grab beers and use your brains
Photograph: Courtesy Dorchester Brewing Co.

Grab beers and use your brains

Break the ice over beers and trivia. Some of the best craft breweries around Boston host trivia nights, where people can nurse some drafts and put their knowledge to the test for a fun evening out. For the cost of a couple beers, you and a date can sit back, relax, casually learn about one another and keep the conversation flowing, with the help of those trusty trivia questions. Dorchester Brewing Co. is known to host weekly trivia nights every Wednesday and they award prize-winners with gift cards, which means you could also score some money to use for a second date.

  • Restaurants
  • French
  • Back Bay
  • price 3 of 4

Conveniently located across from the Boston Public Garden, Bistro du Midi is just the place to stop in for a glass of wine and a chocolate soufflé after a stroll in the park. Francophiles enjoy various authentic touches, especially when it comes to the well-stocked wine cellar that includes some amazing finds from Burgundy and Bordeaux. And if you are watching your wallet, this is a great way to enjoy the ambiance without breaking the bank.

Have a cafe date
Photograph: Courtesy Sofra

Have a cafe date

Just about everyone loves a sweet treat, so stand out from the crowd and ask someone out for pastry. There are plenty of options around town: Get cannoli to-go from Modern Pastry and eat them on the waterfront; grab stunning works of edible art at Jonquils Cafe and then go window-shopping on Newbury Street; or indulge at Sofra and stroll through the picturesque gardens at Mount Auburn Cemetery. No matter which place you choose, you can easily enjoy some of the best desserts throughout the city with your date for under $20.

  • Bars
  • Cocktail bars
  • South Boston
  • price 2 of 4

Nothing lets you loosen up during a date quite like hard alcohol. Boston’s own GrandTen Distillery offers tours and tastings within its Southie space each weekend—the perfect opportunity to get to know someone and learn all about the spirit-making process. Tickets are $15 per person, which covers a 45-minute tour of the craft facility and sampling three small-batch liquors. If you have a bigger budget, stick around the bar and enjoy some cocktails made with GrandTen’s creations. 

Walk the Greenway and grab a bite
Photograph: Courtesy gconservancy

Walk the Greenway and grab a bite

Relish in some fresh air and good conversation with a walk down the Rose Kennedy Greenway. The stretch of parks, which runs for a mile and a half downtown, will lead you down a series of gardens, art installations and water views. Start at South Station and make your way down to the North End, where you can pop into the Boston Public Market to grab a snack or refreshing beverage. Take your goodies to-go and enjoy them on the benches or swings to continue chatting in front of the fountains by Haymarket.

Explore a market and get a local spread

While some open-air markets understandably shut down for the cold season, there’s also a handful of local markets that happen to emerge each winter. Bring a date to the Winter Farmers Markets in Brighton or Somerville, and spend your weekend morning perusing the provisions offered. Purchase the makings of a meal that you can then prepare together, buy some bites (like bread, cheese and mead) for a cozy happy hour, or simply snag some delicious snacks and enjoy them on site. 

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