Few years since I’ve been there, but I did visit the place about 20 times for work. For a view of the city, the Hancock tower is pretty good or the Bay Towers office block which has a three story restaurant near the top (proposed to my future wife there). Also Helicopter flights at night are amazing but expensive.
You have to do the DUKW tour which has some old WWII amphibious vehicles driving in and out of the waterways.
Don’t bother with cheers bar, very small and dull but the Italian quarter is ace or it used to be. Was under the freeway I think has come down now with the big dig. All around the state house is nice as is most of the area around MU, you might as well go and have a walk round the quad. It’s not oxford or cambridge but it’s very impressive.
Downtown boston was a bit of a dump when I was there, but may be better now. All the stuff around the river is pretty cool (beware of a million joggers) and they have a fantastic outdoor stage – worth checking what’s one – we say the ‘bluemen’ or some such thing was fab.
Not sure on eating/accom now probably all changed. In terms of retail therapy stay out of Tiffiny’s tho – ask me how I know 😉
There is loads of great history there (Paul Revere/Boston Tea Party/Bunker hill/etc) but if you’re not intersted in that, it’s still pretty cool to walk down the old brownstones, near downtown to soak up a bit of Boston.
if you fancy a bit of real ‘southie’ on the south side of the river (where the client I worked for was), there are some ace irish bars but it is a bit rough (or used to be), not dangerous just a bit, er, spit and sawdust.