Shopping center with many stores & restaurants comprising 3 historic market buildings & a promenade. Emily loved visiting Faneuil Hall with her friends in High School and it remains one of her favorite spots for cannolis and street performers.
Boston's Central Park. Emily's parents took her and her sisters here every year to traverse the "Make way for Ducklings" tour which culminated in a jaunt on a swan boat in the common and a few pictures on the duck statues. And before her, George Baumgarten would visit the same swan boats with his brothers and sisters with Emily's Oma and Opa back in the day. 10/10 would recommend.
In honor of Zach and Emily's Italian heritage, visit the North End, Boston's Italian quarter. Highlights include the many excellent pizza and pasta joints, and you can't leave without getting a cannoli at Mike's Pastries (Modern Pastry if you are a traitor). You can also visit Old North Church, the oldest standing church in Boston, from which Paul Revere's midnight ride took place ("One if by land, two if by sea"), that preceded the battles of Lexington and Concord which started the American Revolution. But the best part of the North End is the old cobblestone streets and brick buildings that line them.
Boston's Oak Street or Madison Avenue for the shoppers amongst us. Take a walk down Boston's swankiest shopping street from the Common down to Massachusetts Ave, you will not be disappointed by the array of window shopping and cafes. Emily used to frequent these shops with her bridesmaid, Ruthann Barry, who would somehow convince the shopkeepers that the two 15-year-olds were not too poor to be there.
If cobblestone streets are your thing, or even if you're not sure if they are, take a jaunt around Beacon Hill to absorb the American history (and watch your step!). Beacon Hill is home to some of the most historic buildings in the United States and the hills will have all of our Chicago friends and family wishing Chicago wasn't so flat.
For a glimpse of the harbor, Rowes Wharf is a great stop. To get there, you should take the Greenway, which is layered with fountains and parks among the busy streets. In prior decades, George Baumgarten would go in on the boat from Hull or Hingham to Rowes Wharf during his time at Fidelity. Not a bad commute, I'd say!