Trip Snapshot

Arrive early on a Friday evening and take Monday off - you can spend Saturday exploring Downtown, the Seaport District, Back Bay and Beacon Hill, Sunday escaping to the countryside for apples and wine, and Monday morning trotting through Cambridge before catching an evening flight.

When I visited one fall, I made the most of my time by simultaneously signing up for a half marathon, which I don’t recommend entirely because you’ll be fairly immobile the day after - but, I’ll suffer through truly anything for a ginger morning bun from Tatte. PS - Tatte has officially opened a DC location!

Eat

Boston’s food scene can hold its own, but it helps to do some digging in advance you that you have a few destinations in mind - it’s not NYC, where within a three block radius, you could find almost everything you need.

Shop & Stay

Back Bay is the main shopping corridor, if you are looking to hit up national brands that you might not otherwise have in your city. If you are looking for something more local, I recommend spending time in Cambridge and South End, as well as Charles Street in Beacon Hill, which are all speckled with mom and pop shops. The Seaport District is worth peeking into if you are already in the area - the new development is highly contentious, but the Pop Up Village is a retail concept worth exploring (Glossier once called the entire place home for a season).

Walk & Wander

Boston has many charming areas to explore - only parts of the city follow a true urban grid, so be prepared to get a little lost! The downtown area is a quilt of mismatched blocks, each packed with some very historic architecture. Cambridge feels much calmer - there are some beautiful homes that line the streets, with Harvard’s campus anchoring much of the experience.