9-10 days itinerary for Tuscany


New member
Hi fellow travellers,

I'm freshly registered in this forum as I found it really useful for planning our October trip in Tuscany.

Me and my girlfriend will arrive on 11th Oct in the afternoon at Pisa Airport and leave on 20th Oct in the afternoon there again.

We plan to have at least 2 nights in Florence and 3 more in Val D'Orcia region (some village or agriturismo) but didn't yet decided how to plan our trip. We consider renting a car but would definitely not do that in Florence as we have some experience with driving in Italian cities, even smaller than Firenze.

We are not so much into museums and history but mostly small art shops, street life, local food, wine, beer, scenic views, relax (particularly for this trip), etc.

Places on the list are:
Florence, San Gimignano, Siena, Chianti region, Val D'Orcia, Cortona, Arezzo and of course some small villages on the way. We might consider Lucca and the area but not so sure.

Any itinerary proposals/recommendation will be more than helpful.

Do you think Umbria could be included to the trip or would be very optimistic. Or maybe Tuscany coastline?


The Tuscan Expert ;-)
Staff member
Since you arrive and depart in Pisa, you might consider spending some time there - at least a half day - either at the start or end of your trip. I would make my way first to Florence and not have a car at all until you're done with Florence and moving out to the country. So I'd suggest finding a place to stay that is central in Florence so you're close to all of the sights, then moving out, renting the car and then finding a base or two for the rest of your stay in Tuscany. I would suggest the first in central Chianti area and then maybe moving on down to the Val d'Orcia area. It would help cut down on driving, although most of what you want to see is pretty central Tuscany and if you were to stay around Siena, all drives around would be more or less the same. Take a look at some of the itineraries on here: http://www.discovertuscany.com/itineraries-in-tuscany/ - particularly the 7 day one.

You can rent out of Florence center and return the car in Pisa - more info here: http://www.visitflorence.com/florence-car-rental/

Overall, I would suggest 2-3 days in Florence, 3 days in Chianti (drive around Chianti, day in Siena, another day in San Gimignano and surroundings) and 3 days in Val d'Orcia (Montalcino, San Quirico, Pienza on one day, Montepulciano on another, then Arezzo and Cortona on another). Pisa either at start or end and you've pretty much covered your days. When you're in Val d'Orcia, you might be able to include a day trip down in Umbria to Perugia, maybe if you put in Montepulciano into one other day. Remain flexible and see once you're here whether you want to do it or not - as a day trip.

If you need help in finding places to stay, start here: http://www.discovertuscany.com/tuscany-accommodation/

Let us know if you have more questions :)


Well-known member
Adding the coast


I totally agree with Lourdes about adding Pisa to your itin - in fact I suggest you do it at the end of your stay, so that you are close to the airport on your last day.

If you want to get some time in at the coast, you could look at adding Livorno to your itinerary. It is easy to reach from Pisa (even by train, so you can get rid of the car early) and it is particularly rich in things to see and do...especially the boat ride!


Buon Viaggio,

Donna Denise


New member
Thank you very much Lourdes and Donna Denise,

The itinerary proposed by Lourdes sounds very close to the one I was thinking of today.

Please let me know your thoughts about it:

11th – Pisa Airport - Florence (overnight)
12th – Florence (overnight)
13th – Florence - Lucca - Florence (overnight)
14th – Florence Airport (rent-a-car) - Volterra – San Gimignano (overnight)
15th – San Gimignano - Siena – San Gimignano (overnight)
16th – San Gimignano - Chianti – San Quirico D’Orcia (overnight)
17th – Val D’Orcia – San Quirico D’Orcia (overnight)
18th – San Quirico D'Orcia - Cortona – Arezzo - Anghiari – San Quirico D'Orcia (overnight)
19th – Florence Airport (return the car) - Pisa – Pisa (overnight)
20th – Pisa - Pisa Airport

San Gimignano is roughly fixed as a stop - it could be also Volterra, Colle Val D'Elsa, Siena or somewhere in Chianti.
It also depends on the accommodation we'd find - we could spend 1 night more in that place as I know that some owners prefer min 3 night stay.

As I see there won't be any chance for the seaside with this itinerary - strange for a surfer, isn't it :rolleyes:
Last edited:


The Tuscan Expert ;-)
Staff member
I am not sure that Tuscany is particularly well known as a surfing destination so you should most definitely enjoy the rest - the great views, food and wine, history and atmosphere of the towns ;-)

The itinerary looks good and so do your bases -- San Gimignano (or nearby in the countryside) would be a good central point for the trips to Volterra, Siena and Chianti. So is San Quirico for the Val d'Orcia area.

I think it looks good! :cool: