Just pick something and go with it. I've been to NY 3 times and have yet to go into anything approximating a night club, and I haven't really done any significant shopping. But I've been to several Broadway shows (original cast of Rent, thank you very much), SNL, a cruise out of NY, Metropolitan Museum of Art, Ellis Island, Times Square, had lunch with John Kennedy Junior (ok, he was at the same restaurant at the same time - I count it) the Twin Towers on a very strange Sunday when we somehow found ourselves inside a locked building... You just have to decide what your priority is (I'm a museum geek), and start there. Then you can get a better idea of what to do next time.

Since you mentioned late Oct, I'd suggest using that car and going to Salem, MA for all their witch trial Halloween fun. On the ride you'd get to see the fall foliage of peak color in New England (I've been told it's last week of Oct though the leaves are already turning, so I'm not convinced 100%).

Are you driving from NYC to Boston? I'd suggest going the southern route through CT and stopping at Mohegan Sun or Foxwoods (I prefer Mohegan as it's so pretty inside) for some good food, bars, shopping, and I also think penny slots on silly animated machines are fun. I can make $20 last for about 3 hours there!)

If you like Italian food, go to Hanover St in Boston's North End. You can't go wrong with any restaurant there. If the boyfriend likes Sam Adams beer perhaps he would like to visit the Sam Adams Brewery in Jamaica Plain. The New England Aquarium is something different to visit. I like the idea of visiting Salem in October but it is a bit touristy. The news stations usually have peak foliage weeks posted all fall. It won't be as vibrant as usual since there was not a lot of precipitation this year

Grimaldis for pizza (cash only), Metropolitan Museum (Sarafina's for Italian food walking distance), Highline Park....and the Staten Island Ferry (free), Central Park...Ellis Island (but you need tickets purchased in advance)...Upper East Side for expensive browsing...Did I mention that I love New York?

I'd go to Harpoon over Sam Adams any day - much better value. There's also a tour of Fenway Park as this is the 100 year anniversary of the park. (90% of the time that's free with a AAA membership. Shouldn't be, but generally is), Duck tours I hear are fun (but haven't ever done one), I'm also a fan of the Museum of Science, and the Museum of Fine Arts.

Still thinking. I should ask my students what is most fun to do. 17-18 year olds generally know what's up.

I forgot about the Highline! The highline is amazing, I could spend hours there.