If you had one or two days to spend in Tuscany as a day trip from Florence or staying over for one night, where would you choose to spend your time and why?

(San Gimignano, Montepulciano, Siena, Cortona, Elba, or somewhere else?)

TTT because I'm curious too!

Krisa - For me it would have to be Siena.

You see, I'm addicted to panforte

Steve

My husband and I aren't "tour people", but one of the highlights of our recent trip to Florence was "The Best of Tuscany" tour, offered by Walking Tours of Florence. It featured a small group (four couples) with an expert English speaking guide who took us to Siena for a few hours in the morning, to a lovely wine estate in the Tuscan countryside for lunch, and then to San Gimignano for the afternoon. It was very loose and unstructured, and my husband and I branched off and did our own thing at both of the medieval towns. It was a real bargain at $125 euros each, including our wonderful lunch of wine and Tuscan treats.

Pienza

1st day: San Gimignano-Monterrigioni-Siena (sleep in Siena)

2n day: Siena-Montalcino-San Quirico-Pienza-Montepulciano (return to Firenze)

Or day trips to San Gimignano-Siena, Pisa-Lucca or Arezzo.

You don't mention your choice of travel - bus, train, car rental. If you want to rent a car for the day, my recommendation would be to drive to Siena early one morning, tour the city and have lunch, overnight in Castellina in Chianti, which is a lovely town with several good restaurants. The next morning you could drive through the Chianti region, perhaps schedule a tour and lunch at a wine estate and then return to Florence.

With a car, there are other choices - an overnight in either Pienza or Montepulciano would allow you to drive through the dramatic Crete Sinese and enjoy some Vino Nobile. Then there is Montalcino - a lovely, small town with brunello vineyards and abbeys close by.

If you want to train and spend the day, hmmm, hard choice between Lucca and Siena. You don't mention the time of year of your trip. If presented with this choice on a lovely spring or fall day, I couldn't imagine anything more fantastic than a visit to either Siena or Lucca.

It's a difficult decision. You will be somewhat limited by transportation, so make that choice first.

Sienna is wonderful for city life. Pienza and San Gimignano are first choices for more relaxing day trips and would be right close by...I recommend a car and a picnic in whichever places you choose.Enjoy. There are no bad choices here just a lack of time to get to all the lovely places on your wish list!

thanks for the advice...since i've posted this we have decided to spend 4 nights in tuscany (probably skipping florence all together)...we are college students so can't rent a car...

right now we are debating between staying in siena or san gimignano...i know that siena is probably a better hub transportation wise but think san gimi looks beautiful...

any opinions?

San Gimignano is lovely but if you want to use a town as a base to see other sites, choose accordingly.

Between the two, especially if I were still college age, I would choose Siena. There is a large student population there and you will find more to do. And even at my age, when one might assume that I would choose a small, quiet town, I would opt for Siena.

We spent 3 nights in a Fattoria just outside San Gimignano and really liked it but our kids LOVED Sienna! It has that certain something that is exciting and quaint and sophisticated at the same time.
Given that you can't get a car it would certainly be easier to stay in Sienna and then go by bus to many locations. Staying out in the countryside is lovely but we really had to have a car to get around from our tuscan farmhouse.
Have a lovely time!

If you are taking public transportation and want to go to Siena, take the bus. The train does not go directly to Siena and will take much longer than the bus.

Check with the tourist info office across from the front of the train station (on the back side of the block where the Santa Maria Novella Church is.) I believe the blue inter-city busses leave from near there.

My wife and I rode the bus from Siena to Florence several years ago.... a nice ride through Tuscany ...about an hour long.