Join Date: Sep 2005
Location: Lafayette, CO, USA
Programs: SPG Lifetime Plat, AA Gold, UA Gold, DL Silver, HH Gold, Vail Epic
Posts: 9,096
Do you fly back out of Milan? If you drop Milan to just 1 night and add a night in Rome, then you could do a Fifth Night Free award in Rome.
You should also read through some threads over in FT's Italy forum. There are a number of other threads with similarly aggressive itineraries.