The Hilton Amex earns 3 points for every Dollar spent; the Starwood Amex earns 1 point per Dollar. But point redemption is roughly 3 times more "expensive" at Hilton. A category one Hilton is 10,000 HHonors points per night. A category one Starwood is 3000 Starpoints per night (and 2000 on weekends). Category Four is similar: 30,000 points at Hilton vs. 10,000 Starwood points. The main difference is that Starwood hotels are generally nicer (a category four Starwood is usually better than a category four Hilton) and Starwood doesn't have blackouts or capacity controls--if they have a free room, it's yours. The main downside is that Starwood has a more limited range of properties than Hilton. However, if Italy is your goal, that's Starwood's strongest country in Europe and their properties there are really nice. Hilton's strongest country in Europe is the United Kingdom.