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Tuscany Help

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My husband and I will be in Italy towards the end of August and are trying to work out a plan.

We will be flying in and out from Rome.

The plan was to spend 8 nights in Rome and then 5 nights in Sorrento. But my well travelled daughter has suggested that 8 nights in Rome is way too long for August. Her exact words were: "after a few days with the crowds and the heat, you will want to poke your eyeballs out".

So now the plan will be:
Rome 4 nights
Tuscany 4 nights
Sorrento 5 nights.

We have already booked the train from Rome to Naples and the departure time is 11.50am. So wherever we stay in Tuscany we will need to be back in Rome in the morning with the car dropped off and ready to catch our train. The easiest will be to drop off and pick up a car at Rome Termini. (I know it is crazy to get in and out of Rome, but we have driven in Italy/France before, and are willing to give it a try)

So I now have 2 options for Tuscany
1. Spend the entire 4 nights at http://www.locanda-cortona.com near Cortona.
Driving time is 2.5 hours to Rome
Con: the distance returning to Rome to catch the train by midday.
Pro is the amazing views this place offers and it looks like such a great place to stay.

2. Spend 3 nights at www.vicchiomaggio.it in Grieve in Chianti for 3 nights.
The last night somewhere a bit south of Orvieto (not sure where) and reduce the driving time from 2.5 hours to 1.5 hours.
Pro: closer to Rome on the return trip and a great place to stay
Con is the distance to get there on the way out of Rome (3.5 hours) and staying somewhere different on the last night (although this should not really matter)

For those that know the area, which will be the better option at that time of the year.

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