July 13, 2014, 10:28 PM
July 16, 2014, 06:41 PM
Tuscany is a very popular destination. Accommodation is generally booked ahead of time... and September is still a busy month. The only way you can "wing it" and actually find accommodation day by day is by either heading to the local tourism office and hope they have an idea of lodgings in their area that are empty that night or by going online and looking at the big travel websites to see who has availability for that night. NOT all cute, charming farmhouses are on the cutting edge of technology, nor use computer software to keep track of their bookings (yes, I know this from personal contact with the owners!) So you'll be limited to whatever you do find through these two channels. There are no "vacancy" signs anywhere here, it just isn't cultural practice. So rather than spend time visiting the charming, historical center, enjoying great food and wine, are you going to spend that precious time looking for where to sleep that evening? I don't recommend it!
So go online now (start by browsing through www.tuscanyaccommodation.com) and start making note of ones you like. If they have online booking, you can already check if your dates are still free.
As far as car vs. train - all of your planned destinations can be reached by train or bus easily except for Montepulciano. You can reach it with bus from Siena, but takes careful planning... and a car would make it easier for you to tour through the countryside there, stopping to take pictures of the beautiful landscapes when you want to.
If you have 7 days, consider renting a villa/farmhouse apartment (or 2 separate ones depending on size) and staying there the whole week, renting a car and doing day trips. As long as you stay centrally driving time is limited. You won't have to be packing and unpacking your suitcase every night, you won't have to worry about where to sleep every night (if you were thinking of moving around each night) and spend more time seeing the destinations you want to visit.
Italy and Tuscany is "small" relatively speaking, but it is "concentrated" with many, many sights to see. So you'll need a whole day in Florence, a whole day in Siena, while Pisa and Lucca are often done in one day since they are close to each other but really do deserve a day each, as does San Gimignano (a small town that offers a lot to see and visit and enjoy for a whole day there). CT requires at least 2 days really... so you've run out of days already If this is a first time for you in visiting Tuscany, I'd suggest taking it slowly and maybe cutting out something (like CT, as it is the farthest and not in Tuscany anymore) to better enjoy what you see and do.
As far as accommodation - if you give us ideas of what you like after browsing the site above, we can offer more specific recommendations on places to stay at. I'd suggest Chianti as a very general, central area to stay in for starters