Ooh good one! I'm a little out of touch been years but I'll give a go. No particular order.
  1. Go have a drink at the top of the pru
  2. Cliche, but Faneuil hall for Christmas shopping
  3. If you have a day you should do the freedom trail- see the key historical sites
  4. take a ferry to George's island for a picnic
  5. The Aquarium
  6. Haven't done it yet but I want to go to the "new" modern art museum on fan pier
  7. Isabela Stuart Gardner museum
  8. Game at fenway Park of course
  9. Head of the Charles in the fall
  10. Patriots day marathon watching day drinking watching the sox game in a bar
  11. see the BSO or the pops at Symphony hall
  12. Bike ride along the charles
  13. Public gardens- maybe Swan boat ride. Never done it tho.
  14. Coolidge corner cinema has some fun stuff.