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

By Adam Branco

I hope you all enjoyed the first installment of this $20 date series. If you haven't checked it out yet, click here.

If you're looking for more ideas, don't worry. Here's another list for you.

How Can You Not Be Romantic About Baseball at Fenway Park

Fenway Park Student 9's:  This one's for the students; after all, there are about 200,000 of them in the Boston area. Fenway's the Mecca and a game there is one of the quintessential Boston experiences, but tickets can get expensive quickly. Luckily, there's the Student 9s program. As long as you have a working school email address, you can get discounted $9 tickets from the Red Sox website. Every time I'm there, I see hoards of BU students walking over to enjoy the game in right field.

All the Classic Pinball Games in Bow Market

Pinball in Bow Market: Bow Market, one of the great gems of Somerville and a stop on each of my Union Square tours, now has a cozy pinball arcade with 11 machines ranging from the 1970s to the 1990s. They have a machine inside for change, and most games are only about $1 - $3 to play, so bring a $20 bill and you’ll be able to play quite a few games between the two of you.

A Jamaica Plain Gem at the Arnold Arboretum

The Arnold Arboretum: A botanical research institution and free public park affiliated with Harvard University and located by the Forest Hills stop in Jamaica Plain, the Arboretum is one of Boston's prettiest escapes from busy metropolitan life and a wonderful spot to wander around. I've biked through it with friends, had picnics there, and walked through it aimlessly more times than I can count.

A Date on Wheels with Blue Bikes

Blue biking day pass: As someone in the top 1% of Blue Bike riders in the city, I'm rather biased when I say that it's one of the best ways to explore the city. It also makes for a great $20 date, as it's only $10 per person for 24 hours of access to the bikes with free unlocks of classic bikes and e-bikes. Per the website, you can keep a bike out for up to 2 hours at a time. If you're enjoying a long ride and want to keep a bike out longer than 2 hours at a time, it’s only an extra $0.25 per minute. When you choose an e-bike you'll pay $0.25/min for the duration of your ride with no unlock fee. You can take a bike out from any station within the system and return it to any other station. 

Free Admission at the Harvard Art Museums

Harvard Art Museum free admission: The Harvard Art Museum is now free admission for all visitors! If you're ever in the area, they have some fascinating pieces of work and on the final Thursday of every month they keep it open late for food, drinks, music, and rotating exhibitions.

Boston Sunsets at Dorchester Heights

Slices at Alfredo’s and Sunset at Dorchester Heights – When I lived in a South Boston sublet on Telegraph St from the beginning of August to the end of December 2020, Dorchester Heights became one of my favorite local hangout spots. I also saw 4 proposals up there during that summer, so clearly people see it as a rather romantic spot. Get some pizza slices (or even a sub) at Alfredo’s* at the base of Telegraph St, stroll up to the top of the hill, and enjoy.

*You can also substitute this for a 4-pack or a cheap bottle of wine.

Longstanding Cambridge Music Talent at The Lilypad

Jazz at The Lilypad: An intimate 80-person capacity (60 for seated shows) venue in Inman Square, the Lilypad is largely known for its bebop and avant-garde jazz scene. They have shows for as cheap as $10 per person, and shows featuring the Jerry Bergonzi Quartet and the Fringe (who recently celebrated 50 years as a group) are $10 for student tickets.

Oyster Happy Hour Deals in Boston

$1 Oysters: Oysters are delicious, but can run up a serious bill very quickly. Additionally, Boston famously doesn't have happy hour, but restaurants have attempted to skate by that rule by offering discounted food since they're not allowed to offer discounted drinks. You can find $1 oysters throughout the week in downtown Boston, Southie, Dorchester, Somerville, Cambridge, Charlestown, and more neighborhoods.

An Ice Cream Date in Boston and Cambridge

Ice cream – Ice cream's my favorite food and it makes for a great casual date. When it gets warmer, I'll make a whole blog about it, but for now here's a pic from Toscanini's, one of the Boston area's most notable ice cream shops.

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.