Thanks for the comments. RyanAir is unbelievably cheap, great tip! So this is what I think I'm going to book:

JFK-CDG-JFK AA award, economy- 40,000miles x2 = 80,000 miles
CDG-Venice on RyanAir (~$20)
Venice-Florence via train/driving
Florence-Rome via train/driving
Rome-CDG on RyanAir (~$20)

Next question - is there anyway to upgrade other than an OpUp? Can you use eVIPs with award tickets or is that just a waste? There was no business awards availability for the dates i'm after (Nov-17 to Nov-27, JFK-CDG).

I have just been using AA.com to search all these things - should I be calling AA directly as well to see what they can come up with or will it be exactly the same?