Myself husband and two year old are looking to visit Tuscany this year and I'm stuck between May and September. We have never visited before and I'm wondering which month will be better weather wise. We will have a car for 10 days so will be out and about. Thanks
Both are actually great months however with a two year old, I would be inclined to suggest more May. Daylight hours are getting longer and will compensate for a slower itinerary accommodating the napping habits and short attention span of a toddler.
May is normally low or mid season so you should get great prices. You might want to look at accommodations that cater to kids - with lots of fun activities for all ages.