Florence to Siena & San Gimignano - doable in one day and how?

I think that would be a really long day but if you get a very early start you could probably make it. Get a bus schedule from Siena to San G before you go and compare it to the timetable for the train. If I remember right, the buses that go out to the surrounding towns from Siena aren't at the train station. There is a bus terminal of sorts where all the buses turn around at Siena and go out from there. It's been a couple of years since I've done this but it's not difficult to navigate.

Siena can easily keep you entertained the whole day and leave you no time to visit anything else.
Visit San Gimignano separately, maybe combining it with something else small in the vicinity (Volterra, Colle VE, Certaldo, Monteriggioni). I know it's hard by bus.

Jennifer, you are in luck. Grayline has a one-day tour to both. In Florence, Grayline operates as CAF Tours. Their nice tour buses depart Florence from near the main train station. They travel to San Gimignano and you get to self-tour for about 90 minutes. Then, they take you to Siena where you are there for about 4 hours. This portion has a guided tour of Siena. I'm speaking from experience as my wife and I have taken this one-day bus tour. 55Euro as I see on their web page. http://www.caftours.com/ Here's a map of where CAF is located in Florence. They've moved since we took this tour. http://gyazo.com/af188cd82daaf5da879f3781ce4af410 On the address, you see 151 red. Business have red address lettering. Residences have black. Wait until you see how this works. The red addresses are consecutive and so are the black addresses. But both together, they are not consecutive. Also, there are numerous 4-way intersections in Florence where all four streets entering the intersection have different names. What a hoot. Very special. We just love it.

Since Larry started with the crazy numeration system of Florence streets I'll add more.

Number system in Florence streets is based on the river Arno and the direction of water flow of the river Arno, which is from East to West.

For streets parallel to the river (East-West), the numbers grow in the same direction as the water flow, from East to West. With even numbers on the right and odd numbers on the left.

For streets perpendicular to the river (north south), the numbers grow as you walk away from the river. Therefore perpendicular streets on the north bank the numbers grow as you go farther north. The opposite for the perpendicular streets in the Oltrarno (southern bank). Even numbers are still on the right and odd numbers on the left.

For the squares, the numbers grow sequentially (1,2, 3 etc.) in a clockwise direction, starting from....you guessed it, from the corner with the Street that takes you to the river Arno.

In 1966, when the Arno flooded Florence, the water was therefore flowing in the streets according to the numbers. Wasn't that neat? Leonardo must have come up with that system.

My preference would be to spend the whole day in Siena, which has plenty to see, and not to add extra travel time. With "only" 8 buses per day from Siena to San Gim, taking 1.25 hours, your afternoon schedule would not be very flexible.

Thanks for all the advice. I think we'll stick with Siena for the day and San Gim will have to be for another trip to Italy. We are doing a lot in 3 weeks as it is.

Jennifer, my personal suggestion for a day in Siena would be to stay there into the evening, before returning to Florence. Siena is lovely but with many day trippers during the heart of the day, very congested and quite touristy. Once you get into the late afternoon and evening, and the tour buses and other day trippers move along, the historic city becomes magical and much more relaxing. Especially so once the old public buildings are illuminated.

Oh Larry is so right! The evenings in Siena are truly magical. Get a gelato (go ahead, order 3 flavors!) and wander around - don't be afraid to turn off the main street. Find yourself a great seat on the Campo, have a glass of wine and just "be" for a while. There's no reason to rush or to do anything! I can't remember the name - I just follow my nose - but there is a fun outdoor restaurant below the Campo (next the market) that is just great, amazing Tuscan food! You do need to check the return bus schedule if you've decided not to stay the night. And yes, San Gim can wait for another trip to Italy. It will still be there!

Roberto's right on the money. Siena's a one day trip, preferably by bus. The city down the hill from the center city is very congested and parking a car is difficult.
San Gimignano, Volterra and Certaldo are all very do-able in one day from Florence by rental car.

I am thinking of going to Siena for one day while I am staying in Florence. I would like to just go there and not San G. Since I will be myself I was considering the bus tour mentioned. How easy would it be for me to take the bus from Florence and either return that evening or stay one night and return. is it hard to find your way around? Suggestions? Thanks

Yes, Linda, it's easy to find your way around Siena. Try to take direct buses both ways, as that will save both time and hassle. Be sure to have a good travelers description of Siena and its sites with you and read through it before you go, or on the bus. The RS Italy or Tuscany books do a fine job. Either in Florence or once you get to Siena, go to a tourist information office and pick up a good town map for Siena, probably more complete than what's in the book. There are various sites to choose among in Siena, certainly Il Campo and the Duomo complex, I would say. There is a great climb next to the Duomo (il Facciatone), with views of the Duomo, the city and the countryside, as I remember. As I wrote above, I especially enjoyed the evening, including an early dinner right at Il Campo (I stopped for a drink, and enjoyed just being there so much I ordered a risotto for a light supper) and then wandered around the relatively quiet, very beautiful and illuminated town into the evening.
I also enjoy guided day tours as Other Larry mentioned. Without worrying about the logistics of travel, you can see and learn a lot, but in a larger group and without much flexibility of schedule. I was tempted to suggest you or others could take the tour and then stay longer in Siena instead of going back with the group, but It seems that tour goes to Siena in the morning and SG later in the day, so that bright idea wouldn't work so well.

Thanks so much for your reply. I need to think about this.

Linda, it's not necessary to take a bus tour. You may also take the regular buses between Florence & Siena. As others mentioned, Siena is very easy to walk around & appreciate the sites & "just being there". We are returning there again this Fall and looking forward to just being there again, especially in the evening. : )

We're staying at the Hotel Chiusarelli in Siena, where we stayed with a Rick Steves tour.

I will also be taking a day trip to Siena from Florence. Many of these reviews have suggested staying into the evening to relax and enjoy the magical night without the rush of tourists. Is it easy / safe to leave from Siena late into the night? Are there late bus trips?