Siena in October

Suzanne Strauh

New member
My husband and I are coming to Italy in October. he was born there and has been back since his parents left when he was 5. We are celebrating our 30th anniversary.
I have the accommodation booked from Thursday 24 -29 October in Siena. We are wanting a day trip to Florence and a wine tour I think we are flexible on what we want to do any great ideas.


The Tuscan Expert ;-)
Staff member
Ciao Suzanne,

Congrats on the upcoming anniversary!! You'll both love Tuscany and am sure it is extra special for your husband.

Will you be renting a car or depending solely on public transportation? Are you open to doing tours to do some day trips without the need to rent or depend on public transportation?

You can take a look at some tours offered from Siena here, including wine tours to Chianti, to the Brunello di Montalcino area and Montepulciano:
Tours in Siena and from Siena to Tuscany
Tours of Tuscany departing from Siena and Florence

If you want to plan a few day trips on your own that you can easily do with train, I'd suggest a day trip in Florence, a day in Pisa and Lucca (divide the day for each city) and a day in Arezzo. All are lovely towns and there is no need to rent a car to get to them from Siena.

If you do rent a car, then there are additional areas you can get to more easily, such as a drive through Chianti wine region and to its hilltop towns as well as a drive into the Val d'Orcia region where you can stop at Montalcino, San Quirico and Pienza (which you can also do with one of the tours listed on those pages above).

Hope you're enjoying planning the trip! Let us know if you need more ideas ;-)