Originally Posted by saddlesores

are you planning a point-to-point tour or one (or more) hub-n-spoke tours?

if only ten days or so, should be easy enough to pick a couple cities connected by train, 2-3 days ride apart.

fly to italia, spend a few days in city #1 with your wife 'n friend. one day sightseeing with them, a couple days riding in the surrounding countryside.

take a couple days to cycle to city #2, while they take the train.

repeat in city #2.

advantage, you only have to make two hotel reservations for three. you'll only need find lodging on the road for one night.