Shop at Downtown Crossing, home of Filene's, Filene's Basement and Macy's. There are also hundreds of other shops, eateries and street vendors along this pedestrian shopping area of Washington St, Summer St and Winter St. You can get lunch and sit at a cafe table right outside of Filene's.
Take the Orange Line or the Red Line to Downtown Crossing or the Green Line to Park St.
Fondest memory: Update:
It was a sad day for me when Macy's took over Filene's and sealed the fate of Filene's in Downtown Crossing, my favortie department store. With a Macy's just across the street, Filene's was closed and the building sold. The developers have now closed the entire building for renovations with luxury condos planned. This also means that Filene's basement (a separate entity from the regular Filene's department store) has also been temporarily closed until renovations are complete, which is expected to take 2 years! All of the street level take away stands are also closed, including my favorite burrito stand, Sabrosa's and the unique Chilean stand Chacararo's. No word on new locations for those places.
In my opinion, Downtown Crossing is now just a shadow of its former self. Although the mayor is allocating new funding to promote the area, he could start by running a street sweeper on a more regular basis and finding alternative quarters and help for the homeless. I haven't seen much in the way of improvement, and shops are closing right and left. If you want to shop in Boston then my advice for the foreseeable future is to try Newbury and Boylston Streets as well as Faneuil Hall / Quincy Market.
Favorite thing: ..stay at the Meridian Hotel in the heart of the financial district. It is a short walk away from Fannuel Hall where there are many fine drinking establishments. I recommend knocking down a handful of Mcallan 18, neat, at the Black Rose and stirring things up with the locals. Once you get tossed out of one Boston's finest, I recommend taking a short cab ride to the Roxy - I believe it's off Congeressional Ave - but after a few Mcallan's, you may want to ask your friendly Boston cab driver. You will notice a much different crowd here - blazers, turtle necks, and lots of dark clothing - but plenty of local talent. Have a few $10 drinks from their fancy glasses and when you are 'peaking', head next door to the dueling piano bar and finish the night off with an ice cold Budweiser singing Neil Diamond tunes..