I will be in Florence in January with 5 others and we wish to see as much of Tuscany as we can in 5 short days. I would be very happy spending the whole time looking at art and eating gelato, but I do not think that my travel companions would feel the same. Being the only one that has ever been to Italy, I would like to show the most of this beautiful region as I can.
Can anyone suggest day trips?
I am planning on Siena and trying to find the spot where I had the best gnocchi of my life....
Any other kindred advice?

H P,

Tuscany is not at its best in January.

However, in addition to Siena, you can train to Bologna and Orvieto.

You can even do a daytrip to Venice. It will be much less crowded than in the Season.

Do take the no. 7 bus from the train station up to Fiesole for the Etruscan ruins and watch the sun set over the city from the terrace of the Bar Bleu. It's heated.

options:
1. Lucca and Pisa (or just one of them)
2. Drive the Chianti loop stopping in a few places.
3. Siena
4. San Gimignano
4. Volterra
5. Pienza
(or any of the other hill towns)

San Gimignano!!!

Yes, do Fiesole...just a short city bus ride and you end up on a hillside with the ruins mentioned and a monastery up to which you can walk and sidewalk cafes over which you can see Florence in all of its glory.