Boston is not good during the winter. It is very lively during the warm seasons. I recommend a light sweater if you are going to stay out past 4:00 PM. The following locations are places that I know are great. Please suggest any I missed, especially if they fit into the walking path I layed out.

  • Prudential Center
  • Commons and Garden
  • Newbury/Boylston Street
  • Copley Square
  • Downtown & Park Street
  • The Subway
  • Harvard Square

The essential path (2 miles):

I always start from the subway. Get out at Downtown Crossing. Walk up to Park Street. Walk through the Commons and the Garden. Exit the Garden and go to Newbury or Boylston street. Arrive on Copley Square and check the Library. Walk left of the library up to Prudential.

Aside from that you have Harvard Square but that is very far away and therefore not worth it.