Cycling vacation in Tuscany - [Matthew Handford]

Hallo, I am an Italian girl who loves cycling and who has lived 10 years in Tuscany.
The best time to go is probably late September, although the days are shorter: less busy and much cooler. June used to be a good month but it's been three years now that in Italy they have been having scorching temperatures starting from late May. May is probably OK. July and August are not a good choice.

Regarding the area to cycle I would definetely recommend the area South of Siena; there are some villages you just cannot miss. Pienza, Montepulciano, Montalcino e Murlo should all be in your itinerary. Sipping wine while sampling the local cheeses and cold cuts in the terrace of the fortress in Montalcino must have been one of the best moments in my life. San Giminiano is also very pretty but more touristical. Siena is a a very nice town, I like it better than Florence as it is less congested by tour coaches and street vendors. Siena is great for Gothic art while Florence is more Renaissance. If you do not want to miss Florence, you can hop on a diesel train that covers the distance between the two cities in one hour. It is also common to bring bikes on Italian trains, which are also very cheap and not as unreliable as people abroad like to think (unless there is a strike of course).
Some people like to stay in old convents, which are now turning into cheap hotels (I hear they are getting more expensive given the demand); you do not have to attend any of the functions and the food is generally good. If you want to rent a villa you should be able to find help in the nearest Italian Consulate or Italian Ins#####ute. If your budget is high you can contact "Simply Crete", based in London, who have now branched in other Mediterranean areas (they might have a web site); I have seen their brochure for Tuscany and Umbria (I think it might be called Simply Tuscany) and the houses on rent are all faboulous. Book early for these though. A final word of advise. Try to use secondary roads as much as possible and keep in mind that Italian drivers take no prisoner, although I never had an accident.
Get in touch if you need more info. I also know of other great holidays in Italy, especially in the North and Umbria. CIAO