Help with travel itinerary

Good morning and buon ferragosto!
I will be traveling to Tuscany at the beginning of September and I'm looking for some help on the itinerary.
It will be my first time in the region (with the only exception of Florence)and I will be driving.
Here's a draft itinerary (I will arrive from Pavia):
1- Pavia > Carrara/Colonnata > Lucca
2- Lucca > Volterra > San Gimignano
3- Colle Val D'Elsa > Monteriggioni > Chianti > Siena
4- Siena
5- Crete Senesi > Cortona
6- Val D’Orcia (overnight at San Quirico)
7- Val D'Orcia > Campiglia Marittima
8- Livorno
9- Pisa > Pavia
Do you think it is feasible?
I'm not entirely sure, especially about the last couple of days, but I need to go back to Pavia so I thought that route would be the best.
Look forward to your suggestions!
Grazie mille


Well-known member


It is a lot of travelling, and it looks like it means changing accommodations almost every night. - but it is covers most of Tuscany (at least for your first time...there is always more to see on your next trip!)

Chianti is a rather big area to sum up together with those other wonderful towns - so you might want to narrow it down to Castellina in Chianti -

Maybe even consider a night in or near the city before heading over and doing an all day at Siena.

You could look at ending up at Hotel le Fontenelle ( - They offer a shuttle to Siena everyday.

Another one of my favorites in the area is Borgo Argenina, . I had friends stay there and they loved the cooking class.

Buon Viaggio,

Donna Denise