Going to Italy for first time in mid-September. Florence- Siena - S. Ginigmano - Cortona- Montepulciano - Chianti region, etc. We are basically planning trip ourselves. When do we need to start making reservations for small hotels? What's the best way to do this - sources of info, how to...
I start with email to several choices. They may or may not require a credit card. It's safest to fax that (or use a secure website), though I often split the number in separate emails. Also, check Venere.com. We've used them a couple of times for Europe hotels, though they may not have Rick's choices. We were quite happy with our small hotels. I use Tripadvisor.com to get some reviews (Venere has their own revies also), but don't take them as gospel truth.
I've used www.venere.com too. I found the site to be reliable and you can find just about any small town in Italy.
Remember, you have the option to change your mind. Book something that sounds good, keep records, and if you find something better, you can change the town/hotel 24-48 hrs before arrival.
What I've found in several trips to Italy is....allow yourself to change your mind about what you might want to see, you can change hotels too!
I'll also be in Italy in early-mid September and I've booked my hotels already. I wanted decent 2-3 star places for reasonable prices, so it was kind of difficult to find the "perfect" place. I got lucky and got a highly-rated hotel on Tripadvisor for only 75 euros, that was about a month ago and the exact same room is now 115 euros, yikes! I would definitely recommend tripadvisor, though. The reviews are great and I know I felt comfortable booking a place that had lots of positive reviews with little/no negative ones. But I would definitely start booking now - at least for Florence, I can't speak for the other cities as I didn't look for hotels there.