Florence or Siena

Either is wonderful. Florence is larger, and has more to see/do. Siena will be a bit quieter, wonderful side streets to explore. IMO, base in Florence if you are interested in markets, shopping, museums etc. Base in Siena if you want a hill top town feel.

Florence will be easier to use the train from, Siena's center is serviced by bus, train is a bit away, you'd have to taxi to get to it. If you have a car, take that into consideration for parking.

Either would work well, but I would recommend Florence as a home base. Since there are so many things to see in Florence, you would need more time there to fully experience it. Whereas, the highlights of Siena can be covered in a daytrip.

I would highly recommend Florence as your base. We took a day trip to Siena and found it to be very enjoyable, but did not feel we needed more than 1 day there. There is a great deal to do in Florence. While in Florence, I would recommend you having dinner at Nerone's. The food is delicious, and prices are very reasonable. The House white wine is very, very good and inexpensive. We ate there 4 times during our stay in Florence. Enjoy your trip!

As the other posters said both are great but my preference would be to use Siena as a "home base" and day trip to Florence.

Either is just fine. Florence and Siena are 90 minutes apart by train so that's a 3hr. round trip. If you base in Siena, I would suggest estimating how many times you need to travel to Florence. Then, do the opposite. I would suggest staying at the one with the less train travel. Florence is much larger with more to see but you just might like the charm of Siena.

Florence! Siena is charming, especially in the evening, but Florence possesses world class art and architecture and food...and that beautiful Arno River.

I agree that Siena is basically a one-day trip, but one of my special memories is the shell-shaped Il Campo in Siena on a gorgeous night with dark blue sky and a full moon over the tower. The tourists had gone and the Siennese were dining at the several cafes, with the children using the campo for a playground. (The new James Bond movie was filming on Il Campo last summer!) We pulled out a deck of cards and played for hours after supper, feeling a part of the comunity. Then we retired to our hotel just off the piazza; delightful. You might check out making the Siena stop enroute to the CT - not sure of the train connections but it's in the right general direction.

We are also planning a trip to that area- at the beginning of May- and we have reserved a Tuscan villa. It has a Florence address, is accessible by train or bus- so we will not need a car, although we will rent one for a day or two to drive into the Chianti region, to see Siena, etc. My friend who has been there tells me that Siena, Cortona, and Lucca are all great places to visit- but a day or even a half a day for each will do, and then Florence will need lots more time. We will be in our villa with our son and daughter-in-law for a week,and it seemed smarter than trying to find a hotel or moving from place to place. It also proved to be less expensive. Something to consider! We went through two different websites- rentvillas.com and traveltuscany.net. Have fun! I can't wait! Meme from Illinois