Tuscany region for food/nature but not wine-lovers

Personally I think your daytrip options via train, bus, or tour would be better from Florence or Siena. Identify which towns you want to see, then look at Trenitalia to see if they are served by train. Cortona, for example, is served by train out of Camucia. You have to take a bus or taxi to the train station. In Siena you can walk, or take a bus to many towns. When in Siena last year, we met many people using busses to get to Volterra and San Gimignano. We used a car, but found we could easily have done what they did. Rick Steves books have excellent sections on "connections" for each city as a reference for how easy it is to get around using various modes. You might also check out Tours By Roberto out of Siena. Many good daytrip options.
Ciao!

Florence makes more sense if you want to do Siena and San Gimignano. While Cortona is a charming town, it is difficult to get from there to those other places. Also, I don't think there's quite enough to keep you interested for 3 days. Florence offers far more photographic opportunities, especially early in the day and in the evenings. Siena and San Gimignano are also very photogenic. Also, when it comes to food, there are so many more options in Florence. There are great restaurants in Cortona, but nowhere near as many choices. If you don't want touristy, take the train or bus from Florence to Siena as a day trip. It's very straightforward and there's no need to take a guided tour on a bus unless that is really what you want. Once in Siena proper (up the hill from the train station), you are free to wander and do as you please. Siena might be a better base if you want more nature and less urban. Florence is very urban. Siena is a medieval gem, and very easy to get out of the town and into some beautiful countryside. That's harder in Florence. I like Volterra too. Some very dramatic landscapes & great photo opps. One photo I took from the crumbling cliffs at Volterra was used as the page lead for a golfing magazine (see http://www.lodgephoto.com/aboutus.html) I'd say it's easiest to get to many of the smaller Chianti towns without a car, though bus does work if you are well organized. There is a bus service (SITA) from Florence and Siena, but you end up with limited time in your chosen locations and far more waiting. Mathew

Take a look at the 'Slow day in Tuscany' http://www.slow-days.com They do a day trip from Florence into Tuscany taking in the great outdoors, a slow-food restaurant and a hill town or two. There is a wine tasting as well, but but it's not the sort of wine tour where you go from vineyard to vineyard all day. The tour goes a bit off the beaten track so if you really must see Siena and San Gimignano you'll maybe want another tour.

Thanks everyone for this feedback! Sounds like Siena or Florence as a base make more sense. Having looked at a few of the hotel and B&B options for Siena on TripAdvisor, are there pros/cons when it comes to Siena accommodation? Is there a city center to be mindful of? Or given the desire to do day trips out of either location, should proximity to bus/train station be prioritized? -Nan