Suggestions for Itinerary six days from 16th January 2015


New member
Ciao! Lourdes,
I only just discovered your forum last night, it is wonderful, so full of ideas! I am traveling to Tuscany on 16th January, after spending the previous night in Rome. So far I have booked three nights as a base in the beautiful little town of Certaldo, from the 19th to the 21st January. I am wondering where would be the best place to base myself for the three nights 16th to 18th? I will have already spent time in Florence and Siena with my husband, but he needs to get back to Sydney for work, so I am very lucky to have another week to explore the area myself! I have never been to Pisa, Lucca, I would love to see Cortona, Orvieto, Montepulcino, Montalcino, even San Casciano de Bagno (I love Marlena de Blasi's books) just all the lovely small hilltop towns. How hard is it to drive in Tuscany, I am used to driving in very busy Sydney, but have never driven on the right side of the road. Also where would be the best place to rent a car? I read that maybe I should take a train from Rome to perhaps Orvieto, or somewhere else you might suggest, and rent the car from there, also return it there at the end to then take a train back to Rome for my last night 22nd January, before I fly home. It would need to be somewhere that I could drive to easily from Certaldo as I spend the night of the 21st there and my night is booked in Rome for the 22nd.
Any suggestions would be most welcome!
Ciao! Sally


The Tuscan Expert ;-)
Staff member
Ciao Sally,

So glad you found us and hope we can be of help!

Certaldo is a charming town, it is quite central and between Florence and San Gimignano. Since you're here the last days before needing to go back to Rome, and most of the places you want to visit are in southern Tuscany, I'd suggest the other base being in this southern area.

Anywhere between Montepulciano and Cortona would be a good area - you can do day trips to most of the places you're interested in.

A possibility I'd suggest to look into is this: stay in Certaldo first (can you move the booking without penalties?), then move on to southern Tuscany as you'll be closer to Rome, working your way down toward Rome. Driving abroad is not the easiest as it does require resolve and determination - but I don't think it is impossible. The first day or two will be the most challenging, as you do have to get used to driving on the other side of the road. But you'll be traveling along either the motorway, where you can't go wrong, and smaller country roads (2 lanes) where traffic is limited and so you won't be finding really busy situations like in a city. I support not driving at all in Rome nor Florence, lots of traffic and areas that are off limits... so the best choice is to take the train to Orvieto (since you want to visit! two birds with one stone ;) )- and rent out of there. Other possibility is Chiusi.

If you can't move things around, don't worry. Tuscany is pretty small overall, and even the drive from Certaldo down to Rome is around 3.5 hours.
I'd suggest something like this:
16-18th stay somewhere in the Val d'Orcia area, between Montalcino and Montepulciano - From here you can do Cortona and Arezzo one day, the Val d'Orcia the other two days - Montepulciano and San Casciano, Pienza, Montalcino.
19-21th Certaldo - from here you can go to Pisa and Lucca one day, spend some time in Certaldo and visit San Gimignano the second day and the third day explore Siena if you want to go back or head to Volterra & Colle Val d'Elsa to see more splendid views of Tuscany.
On the 22nd, drive down to Orvieto, see it then and return car! ;-)

How does everything sound?