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Photograph: Sarah BentivegnaFormaggio

The 9 best cheap date ideas in Boston

Win them over with these affordable but thoughtful outings

Olivia Vanni
Written by
Olivia Vanni
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Dating in Boston can truly take a toll on your wallet. Whether you’re in a stable relationship or still trying to find that special someone, paying for pricey nights out and regular date nights can really add up, if you’re not careful. Despite our city’s expensive reputation, we do have some affordable options when it comes to taking someone out. We’ve compiled a list of cheap date ideas that are thoughtful, romantic and all cost less than $30 (that’s basically the same price as cocktails for two, plus tip). If you have more money to spend on a special night out, also be sure to check out our guides to 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

  • 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. 

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  • 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.

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  • Bars
  • Downtown

Engage in a little friendly competition with a gaming date at Versus. Located in Downtown Crossing, this arcade and bar features Free Play Friday, when there’s free entry and unlimited playing for anyone who arrives between 5—6pm. Head over right after work for a rendezvous filled with nostalgia—whether it be bonding over old school arcade games like Frogger and Ms. Pacman, video game classics like Mario Kart and SuperSmash Bros., or analog amusements like Giant Jenga and shuffleboard. Without having to pay the usual $5 cover per person, you’ll have the funds to split some loaded Zelda Fries (they’re $12 and covered in melted cheese) or grab milkshakes (they go for $8 a pop, with the option to make them boozy for $4 more). 

Have a dessert date
Photograph: Courtesy Sofra

Have a dessert date

As far as dates go, there’s dinner and there’s drinks, but what about desserts? 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.

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  • 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.

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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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