Very jealous about your Tuscany trip. I have been a few times and really enjoyed it. Obviously the place is beautiful all year round and as much as I would love to say "go in the summer," - and it is true that seeing the Tuscany in the sunshine is beautiful - there is a lot of tourists during these times and even the small villages can be a little hectic. My favourite experience was holiday to Florence in the early spring (late March, early April). I was lucky enough to catch the early sunshine but beat the summer holiday rush. Also, the beautiful countryside looks great in early bloom. Perfect for walking.
Have you ever been to Capri? I am planning on a visit early next year and want to know if I should wait for teh sun or if the winter is still a good time to visit.
Enjoy Your Trip
Life is a roller coaster
Not sure if this helps, but if you are planning on heading to Florence, make sure you pick up a Firenze Card. they are about 60 - 70 euro and give you good travel access around the city.
I found some good information here when I was planning my trip:
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