$20 Dates in Boston: A Food Tour Guide Part I

By Adam Branco

Being single in Boston can be a wonderful adventure if you let it be. I want you all to go to cool places, see new parts of the city, and spend time with people you’re excited about, but I don’t want you to empty your bank account to do so.

So, behold. An ongoing list of $20 (plus or minus a dollar or two) dates that are unique, interactive, and not a couple of rounds of overpriced cocktails downtown for the 3^rd time this month.

North End Sandwiches at Monica's and Dino's

Split a sandwich from Monica’s or Dino's and walk around the North End: The Italian at Monica’s is $20 plus 7% Massachusetts tax, and the steak bomb with the works at Dino’s is $19 price tag plus 7% Massachusetts tax. They’re also huge, so splitting the sandwich between two people shouldn’t be an issue. Take your sandwich and hang out in the Paul Revere Mall, the Rose Fitzgerald Kennedy Greenway, or along the harbor walk.

Free First Thursday's at the Isabella Stewart Gardner Museum

Isabella Stewart Gardner Museum free admission first Thursday of each month: Museum nights will be an ongoing theme for these blogs, but this museum will be the first installment for a couple of specific reasons. First, the ISG is a more uniquely Bostonian museum than the likes of the MFA. Second, it used to be much cheaper when I first went in 2017, but thanks to Covid, inflation, and a Netflix documentary, admission is now $22 per person. In my opinion, it’s not necessarily worth it at that price point. The courtyard is gorgeous, and the origin story and subsequent robbery story are fascinating, but because it’s someone’s personal art collection and much of it was stolen and not replaced, there’s just not a ton to see. If you take your sweet time, you only need an hour and a half there.



That’s where the free admission night comes into play. The museum stays open late, they’ll have music or poetry in the courtyard, the lights are dim, and it’s a lovely date night in one of the more charming locations in Boston. Take the $44 you’ll save between the two of you and allocate it towards the second date.

My Favorite Pizza in Boston and My Favorite View of Boston

Pizza at Santarpio's (and assorted Eastie foods) and walk to the docks: I lived in East Boston for two years. It was wonderful, and I miss it a bunch. It also has the city's best views at the docks along East Pier Dr, and I’ve brought plenty of friends and dates there. Additionally, as a New Haven County-raised pizza snob, Santarpio’s is my favorite pizza in Boston, and a cheese pizza will run you $14 before tax (and tip). Grab a pie, head down to the docks, and enjoy.

Exploring Central Square's Art Scene

Coffee and graffiti hunt in Central Square: This is neither the first nor the last time you’ll see coffee as a casual first date suggestion, but while you’re in Central Square, take advantage of the eclectic art and mural scene. Graffiti Alley is ever-changing, there are some wonderful murals on and off Mass Ave, and if you’re really up for an adventure, the city of Cambridge put together a self-guided art tour. My favorite coffee shops in the neighborhood are Cicada and 1369 Coffee House.

A Cambridge Arcade Night at Roxy's

Roxy’s Arcade: Staying in Cambridge for this one, Roxy’s is a grilled cheese shop and an arcade bar mashed together to create a bit of an adult playground. With $20, you and your date can play at least 4 or 5 different games each and have quite a bit of fun. Just do the best you can to avoid going during peak hours on Friday and Saturday.

Photo courtesy of Roxy's Arcade

One of Boston's Most Creative Communities at SoWa

SoWa: Short for South of Washington St, SoWa is a South End community of artist studios, vintage clothing, galleries, retail shops, design showrooms, and restaurants.  The Vintage Market and art studios upstairs are open every Sunday year-round. The Open Market, featuring over 100 regional and local vendors and food trucks, is open every Sunday from the beginning of May till the end of October. The Christmas Market in the Power Station is also wonderful, and First Fridays, which goes on from 5:00 – 9:00 the first Friday of every month, is free to the public. Go to any of these events for a lovely South End adventure.

Boston's Greatest Musicians at Berklee College of Music

Berklee College of Music performances: I don’t know about you, but I certainly take for granted the sheer amount of talent in the Boston area across an array of industries and specialties. Berklee College of Music is a top 3 to 5 music school in the country right in our backyard, and many of the best musicians in the country perform at the school and all around the city for quite cheap or even free. You’ll also see Berklee students perform in spots like Warehouse XI or throughout the ongoing Sofar Sounds series.

Photo courtesy of Berklee College of Music

Exploring Boston's Parks at the Boston Public Garden and the Esplanade

A sunny day at the Boston Public Garden and the Esplanade: Dating isn't always a walk in the park, but sauntering through the Public Garden and the Esplanade is. It's very hard to beat Boston's green space in the warm weather, and good company would make it even better. Even in the winter, the pond frequently freezes over, which has become one of my favorite Boston traditions and it makes for an eventful stroll.

The Esplanade, a riverfront park running from the West End to Boston University, makes for one of Boston’s most pleasant walks as the weather gets warmer. Stop at the Owl’s Nest for a beer while you’re out and about.

Intern Heaven at Coogan's

$1 Bud Lights at Coogan’s – I’m kidding (unless).

Join Up & Adam Food Tours

But if you feel like you should spend more than $20 on a date, consider going on one of my food tours! Check out upandamfoodtours.com, and email me at info@upandadamfoodtours.com or message me at (508) 271-7124 for more details.