I'm considering taking my wife on our anniversary to Italy using points. A friend suggested a Rome, Tuscany, Venice weeklong trip is their most high recomendation. I haven't done much research yet, but any suggestions? Also, how long in advance, realistically, do I need to plan and coordinate this?
Sounds like a great trip. Save yourself a lot of time and money with an Italian Eurail Pass. You can get from city centers easily and cheaply. Marriott's in Rome and Milan are downtown, Venice the Courtyard is away but the price could save you a lot or just use points.
We don't use organized tours and we take trains & local transportation so lots of research pays off. I spend every spare hour I can get reading the guides & posts because I get so much more out of the trip. On the other hand, my spouse goes with the flow and happily enjoys whatever comes. My feeling is that in order to see 3 places in a week planning is essential. Bottom line though, a week in Italy is -- a week in Itely! Hope you have a great trip.