We did Village Italy as our first tour quite a few years ago. It was almost exactly on this date. Hubby and I don't take or wear jeans only because they are thick, heavy and take longer to dry. We wear our golf pants. They pack well, come out non-wrinkled and dry overnight.
We had some drizzly days and mostly sun. On the drizzly days, it would rain a bit but not all day. After a half hour or so the sun would pop out. We both had light rain jackets and that worked well. We did not take any shorts, but the pants and shirts we had were very comfortable. I will advise that you pack as light as possible. There were many of the small towns that the bus could not drive to the hotel, so you are carrying or pulling a suitcase through the town on cobblestones to get to the hotel. Totally worth it!!
This was our first RS tour out of 7 and they have changed it a bit. I would even consider taking it again. I hope you have a great time.
Also, we flew in to Venice 3 nights early and spent a few days there getting over jet lag. That worked very well. The train to Padua from Venice is a very short ride and easy.
Have a Great Time!