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Boston is the best city to take a first trip as a couple

Romantic cobblestones. A chocolate factory. Pretending to be Matt Damon. You can do it all — together.

Maxx Perkins chose a shady hilltop on Boston Common to propose to Miranda Bendoni in 2021. She said yes. The Missouri couple were visiting Boston, where she is from.Lane Turner/Globe Staff

A lot of people are coming to Boston. Good for them.

There’s history, cuisine, and it’s a good walking city, especially after May.

I would argue that Boston is also a good trip for a first trip for romantic partners.

There’s enough to do keep you busy, it’s got some romantic cobblestones, and if you design your journey right, you can learn plenty about a new significant other’s values and tastes. One walk along the Freedom Trail, for instance, can reveal someone’s politics — how they define freedom and who it’s for. One visit to Fenway Park will show you whether someone is the kind of person who’ll yell “Yankees suck” for no good reason or roll their eyes at the chant.


A trip to Boston can be a window into the soul.

(Not to stress you out or anything.)

If you google the city — or better yet, read the entire Back to Boston section — you’ll know where to go. But if you don’t mind, I’d like to offer my own picks, specifically for new partners visiting the city. I write an advice column and focus on romance, so that’s my lens. Here are five places where I’d take a new significant other while on vacation.

This also works for longtime significant others who want to get to know each other all over again.

1. Delux, 100 Chandler St.

Delux is a restaurant in the South End that’s pretty small with a comfort food menu. The food is tasty, but the best part is the restaurant’s walls, which are covered with albums and tributes to Elvis. This is where you and a new special person can ask each other the following question: “Which of the Delux’s knickknacks/albums would you take to a desert island?” Lesley Gore or the Kinks? What about a bust of Elvis himself? This is a good game played over drinks and quesadillas. Then you can walk around the neighborhood and guess how much the brownstones cost. The answer: a lot!


2. Arnold Arboretum, 125 Arborway Boston

The Arboretum – a 281-acre park and botanical research spot run by Harvard — is not a downtown destination, so perhaps a lot of visitors skip it. But it’s worth finding, and in May there are lilac tours. There are so many lilacs. And international trees! And birds! Spend a morning in nature, walk through the Explorer’s Garden near Bussey Hill (my favorite area). Then have lunch in Jamaica Plain or Roslindale. A sandwich at Ula Cafe puts you next to the Sam Adams Tap Room, housed in the very cool brewery building. Then you get to learn whether your partner is a beer snob.

Lilacs were in full bloom at the Arnold Arboretum in 2021. John Tlumacki/Globe Staff

3. The Red Line

OK, hear me out. Yes, this is public transportation — some would say a means of travel, as opposed to a destination. But the view over the Charles River is sweet, and for pop culture fans, it’s all about the movie. Basically, get on at the Charles/MGH stop. Once you’re halfway over the bridge, play “Good Will Hunting” by sinking down into your seat like an emotionally burdened Matt Damon. Then quickly get up to enjoy the scenery. This is a way to find out whether a) someone has seen “Good Will Hunting” and b) whether they are playful enough to pretend to be Matt Damon in a movie.


4. The Cells, 500 Main St., Cambridge

One of my favorite spots in Cambridge is the The Koch Institute Public Galleries at MIT. It’s a collection of biomedical images — art inspired by research. You can go inside during the day (check in before you go; rules change, these days), but at night, the large round cell art is beautiful and sometimes devastating, especially when you read the labels that explain them. A florescent disc with graffiti-like lines and dots might, upon closer inspection, be the building blocks of a disease. Sometimes I think of the pieces as Rorschach cards. They’re bound to provoke deep conversations about science, health, and hope. Eat nearby at Miracle of Science and enjoy the periodic table menu (Hb for hamburger).

Part of the gallery in 2015. It looks even cooler at night. David L. Ryan/Globe Staff

5. Taza Chocolate Factory, 561 Windsor St., Somerville

That cell trip was a lot of thinking, so it’s time to eat some feelings. The Taza Chocolate Factory includes samples, and the building is in a part of Somerville you might otherwise not see. You can walk from Inman Square. You’ll learn a lot about stone ground chocolate, and whether a partner thinks that chipotle chili, as a flavor, is excellent or gross. Finish with dinner at one of the restaurants in Bow Market, an ever-changing popup experience in Somerville that houses restaurants, shops, and a great area for outdoor seating.


Then kiss goodnight.

Taza Chocolate in 2013. Colm O'Molloy

Meredith Goldstein writes the Love Letters column and can be reached at