Hello! We are a couple from Brazil who will be visiting Italy for the first time in May 2018. We have reserved 8 full days for Tuscany before travelling to Rome but after a lot of reading and itinerary simulations, we do not seem able to put together a sensible programme. There is just too much to see and we've finally agreed we really need help . A first itinerary attempt is below but we can't figure out a number of things:
- should we rent a car all along or just for parts of the itinerary?
- We really want to also have some countryside experience in one agriturismo for at least 3 nights or even more but can't figure out the best location/region to stay that is more suitable to drive around.
- Another dilemma is whether it would be sensible to include Cinque Terre and if yes, is it easy to have a day trip from Florence or it would be better to stay there for one night?
- We would like to visit wineries but we'll be driving so will not be able to drink, of course. Do some wineries offer any transfers our tours that include transport?

Draft itinerary:
Day 1 - arrive at 4pm in Florence by train from Venice (non-refundable train ticket has been purchased already) - check in a central hotel in Florence
Day 2 - explore Florence (no car)
Day 3 - Day trip to Pisa and Lucca by train returning to Florence in the evening (or should we go by car and swap with day 4?)
Day 4 - Day trip to Cinque Terre by train returning to Florence in the evening
Day 5 - Check out from Florence hotel, rent a car and drive to agriturismo near Siena. Explore Siena for the day
Day 6 to 9 - Day trips to ... (San Gimignano, Montalcino, Montepulciano, Chianti, Pienza...) Should we change accommodation or could we stay in the same agriturismo and just drive back and forth every day?
Day 10 - Drive or take train to Rome

We will be grateful for any tips. Thank you very much for making this forum available.

Kind regards,
Ana