Here's what I'm looking for for my Tuscan day trip: Stunning vistas (being in cities the entire trip I want to simply soak in the countryside), enough time to truly explore and relax, and don't want to fight millions of other day-trippers. Are we best off just hiring a driver and visiting little out-of-the-way villages and simply enjoying the drive? Or would I be remiss in excluding one of these beautiful towns? Are the bus rides long and uncomfortable? I wouldn't say price isn't an issue, but I don't want to be miserable either. Thanks!!

It's a very easy train ride from Florence to Cortona (actually to just below Cortona, and then you take a quick taxi or bus ride or a long steep uphill walk up). I vaguely remember it was a very easy bus ride from Florence to Siena. In my opinion, you should NOT miss Siena. I also think it would be perfect if you spent a full day, or p[ossibly an overnight in Cortona, because it would meet all your needs. You could visit the town itself, and also walk on the paths out of town into the countryside. It happens to be a great area for rural walking, even if you just want to walk just a very few miles. If you stay overnight, you can watch the mist rising from the valley below Cortona, and watch the churches emerge from the mist.

I haven't been to Cortona ( my mistake!), but if I were choosing between San Gimignano and Siena, I'd pick San Gimignano despite the crowds. The views from the top of the ramparts and from some of the restaurants inside the walls are exactly what you're looking for. And it's a really fun town to explore, although I'd advise trying to arrive in the late afternoon/early evening when the crowds are much thinner.

We did hire a driver to explore other out of the way towns, and really enjoyed having that option. I can highly recommend Luca Garapa of Hillsandroads.com, who is based in Siena, and knows the surrounding area extremely well. He's a reliable driver, speaks excellent English, and is very good company!

Hope you have a lovely trip.

I've been to all three and for what you state as your requirements I'd pick Siena or possibly Cortona. San Gimi was great but is really crowded during the day with other day trippers. At night it was wonderful (from about 5pm till 10 or so the next morning). It's also the hardest to get to by public transportation. Siena was pleasantly uncrowded during the day and the bus ride from Florence was only about an hour, very cheap (I think about 13 € roundtrip) but was in an airconditioned comfortable bus. Bus drops you off right near the interesting parts of the old city. Even though it is a city, it feels quite rural. Cortona is even smaller, so you'd feel even more like you were in the country, and was definitly not crowded but there wasn't much to do or see there compared to Siena. We did Cortona for just a few hours on the way to someplace else. Siena I did as a day trip from Florence and spent a whole day there. As I said San Gimi we spent the night in which is the best way to see it. All three of these towns I visited in July (but in different years).

Hi IB,

From whence are you departing for your daytrip?

Siena is a city....Cortona and Sangi two very small towns....

"Stunning vistas (being in cities the entire trip I want to simply soak in the countryside)"
This IMHO does not describe Siena.
Ira,as always, asks the most important question for advice to your question.
It really reads like you want a pretty ride in the country with some nice stops.
If you are in Florence for this day trip, I'd suggest a Chianti day trip.
Rent a car or hire a driver.

Thanks to you all for your insights. I guess I'm not surprised there isn't an overall "winner," which just makes this decision even more difficult. To answer Ira's question, we'll be leaving from Florence.

If you are in Florence and have just one day for a Tuscan day trip, I would agree with jabexz and either rent a car or hire a driver and take the Chianti Classico road. You will see stunning scenery, a village or two, stop somewhere charming for lunch and or dinner, perhaps a winery, you get the picture. This is how to soak in the countryside for a day - it will be lovely and you will have a wonderful. I cannot recommend a driver since we have driven ourselves but I'm sure someone else can.