Traveling around Tuscany without reservations

I've done it in that flexible manner in mid-October; September is busier. You can't count on finding exactly what you want when you want it, but if you're amenable to choosing among available options in the general vicinity, then you should not have to sleep in the car. The car makes it easier to reach all possible options. If you're able to call or book online a day ahead, that's usually better than just showing up. I'd at least confirm your options before drinking too much wine.

If you have wifi access and a list of hotels or phones/hotels you could call ahead every day or two and book. The days when you can just roll into town and find listings in the train station or tourist office are over; having to find lodging every night sucks up time you could be enjoying the experience. We came very close to sleeping in the car one May trying to book on the fly. IN our experience we pay more for much less charming lodging when we do it on the fly as well.

At least I would loosely plan and then book a day or two ahead.

Your plan sounds great, just the type of itinerary we like. If you do book a room in advance and are running late, be sure to phone them. We didn't once in Monterosso and our room got sold, the town was booked solid, so we slept in the lobby for a few hours. We were totally stuck, but the hotel owners were super kind and made us sandwiches.

Have a great trip!

gc,

If you haven't driven in Italy before, I assume you're aware of some of the usual "caveats". For example, each driver listed on the rental form will require the compulsory International Driver's Permit, which is used in conjunction with your home D.L. You'll also have to be extremely vigilant to avoid the dreaded ZTL (limited traffic) zones which exist in many Italian towns. Do NOT drive in Florence as the city is just about saturated with automated ZTL cameras. Each pass through one will result in a hefty fine, which you won't know about until several months after you return home. You'll also have to be careful about speed cameras, including the devious Traffic Tutor system.

Siena is not particularly good for parking options, so finding a hotel that offers parking would be a good idea. Having a GPS or at least a good map is also prudent.

Regarding your plan to "wing it", September can be busy in Italy so you may have to spend some time looking for accommodations in some towns (depending on how full they are at the time). You may have to accept something that's not in the area you want, or not at the price or comfort level you're used to. I usually like to have my accommodations pre-booked as I don't like wasting valuable holiday time looking for a place to sleep, especially while I'm hauling all my travel gear in an unfamiliar city.

You might find it helpful to pack along a copy of the RS Italy guidebook, as there are accommodations listed there, including phone numbers and other contact information. Will you be travelling with cell phones?

Good luck!

The best solution would probably be to book ahead the day before or even on the day of your arrival. If you really want to wing it, note that you may use up some time finding a place. September can be busy in Tuscany.

I like your travel plans however I would advise to keep at least a copy of possible choices of places to stay with you and maybe call 1 day ahead to book a room. I found a wonderful place outside of Siena and just like you decided to stay another night. Its nice nt to have schedules

Agree with many posters above that the plan would be nice as long as you have internet/phone access so can always book at least 1 day ahead.
Many reason for posting is just to chime in if you did not know that most everywhere you want to stay won't be reachable by car. You could have to park in a paid lot and then walk with your luggage to the these towns assuming you intent to stay in town, if they are booked you then need to walk to another hotel with your luggage, etc... Could be quite the hassle and inconvenience not to mention say they are all booked you still just paid for parking and now have to drive to another town and repeat the process.
Some hotels may have discounted parking, their own parking spaces or ability to drop off luggage at their door via a pass or ZTL allowance they book for you in advance so there are potential big benefits of booking at least 1 day in advance.
A hotel in Montepulciano for example emailed me a pass so I can drive up to the hotel inside the city walls rather than have to park outside of it like all of the other visitors to town. Without the pass I could not drive in.