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Tuscany in late Oct / early Nov 2016?

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My husband and I are planning a 15 days (excluding international flights travel time) trip to Europe. We would spend 5 days in Paris and wish to combine it with a week in Tuscany and 2-3 days in Florence. Fly open jaw from NYC to Paris and Florence. Will travel between Paris and Florence through a flight or overnight train.

Tuscany - we would stay in a town or max 2 as base and do some day trips. Open to rent a car for few days if public transportation is sparse and having a car makes it easy to cover several smaller towns for a quick visit and drive by. Clarification - we are teetotalers, so Chianti region is not our main focus. I have spent 5 days in Florence earlier, including a day tour to few towns like San Gimignano, Siena, etc.

Questions:

1. How is Tuscany as a place to visit in late Oct / early Nov? I get it that it is difficult to predict the weather. But if it constantly rains, being in the countryside would be frustrating, especially if we are doing day trips to other towns and have a small window of time to enjoy the place. Also, we don't want to complicate driving because of rains in the countryside, we drive sparingly and are not used to it on a daily basis.

2. If at all that makes a difference, should we fly into Florence first and head straight to Tuscany on 22 Oct? Or should we reserve one week in Tuscany towards the end of our trip, so roughly 30 Oct until 5 Nov or so? We would fly back to NYC on 6 Nov from FLR or PAR. Factors to consider are weather (rains. cold, etc), harvests of produce, specific festivals, closure of restaurants and accommodations, etc.

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