Italy is a decently large and varying country. Getting to Rome or Milan will be easier than to the Amalfi Coast or Sicily. Use trains within the country. Summer will be the most difficult time to go via award travel and I find it is either overly crowded with tourists or lacking from locals going on their own vacation. Falls or Spring will probably be the best overall times.

Prices to Italy have been very low so take a look at cash prices via sites such as google.com/flights and compare to what Amex Travel is asking in points. The Amex Travel rate may be more than OTAs which can then be price erased at 1cpp.

Alternatively, you can transfer points to a participating airline transfer partner. Use Award Hacker to see what is possible then you have to do your own searching for award availability.