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Florence, Tuscany & Bologna

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Hi everyone,

We have a trip planned in early October to Italy to the above locations.

Florence 2 nights
Tuscany 4 nights
Bologna 2 nights

I am just trying to figure out the Tuscany side of our trip & need some help. We are wanting to hire a car for the duration of our stay in Tuscany, my thoughts were to pick it up in Lucca (first stop) and then drive to Bologna and drop off there, first of all - what is the most scenic route to Bologna and is it worth the drive or would drop the car in Tuscany and train up?

Secondly - we have 4 days in Tuscany, a little bit of planning is required but really we just want to jump in the car each day and see where we end up, and this means booking the accom each night as we go...good idea or bad idea? should we just choose a base and pre-book? if so where is a nice spot to base ourselves.
The main towns/cities we want to see are:
Lucca
Pisa
Chianti region
Siena
and all the smaller towns in between.......once we are there I guess we will decide on how long we spend there, a day or overnight etc, or move on to the next spot.

My concern is we may find ourselves wasting time searching for accom if we don't book in advance? Also is it easy enough to park in the main towns?

Thanks in advance, any advice would be appreciated. Travelling with fiance, both mid 30's.

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