See the section for Italy of the Trento Bike Pages, which contains some reports on cycling in Tuscany.

On-road itineraries in Toscana and Umbria

By Andreas Caranti
Please Note that this page has been written in 1994, and it's now superseded by several excellent reports you can find under the section for Italy of the Trento Bike Pages.
You may want to look up some Book references.

The following are some of the many possible on-road touring suggestions. When a route is not explicitly indicated, the idea is to avoid the more crowded "Strade Statali" (National Roads) and choose secondary roads. Good maps are essential. Good motoring maps are provided by Touring Club Italiano, and De Agostini. As to more detailed maps, those published by Kompass, on a 1:50 000 scale, are particularly good, but do not cover the entire territory. The scant notes we provide cannot of course replace a good guidebook. A touring biker may take advantage of the services offered by Italian Railways.

Orvieto-Todi on road 79 bis. About 40km on a scenic, winding road. Both towns absolutely worth a visit.

Spoleto-Montefalco-Bevagna. About 30km. Spoleto is well-known, if only for its "Festival dei Due Mondi". Don't miss the Cathedral, which you approach most unusually from above, and "Ponte delle Torri". But the other two towns have also something to offer, among them the pictures in "Museo di San Francesco" in Montefalco, and the medieval square in Bevagna.

Cortona-Montepulciano-Pienza-San Quirico-Bagno Vignoni. About 70km. Very much to be recommended. Extremely pleasant ride on gently winding roads, takes you with manageable ups and downs through towns of incomparable beauty. In the spa hamlet of Bagno Vignoni one can then rest satisfied at Hotel Posta, far from the madding crowd.

Added around Easter, 1995

I've been to San Gimignano for Easter. I was with friends, and nobody had a bike, so I didn't take mine, to avoid playing the antisocial type. The area is great for cycling, if you don't mind going up a few short, steep hills. There is even some interest for off-road cyclists. There is an extensive network of gravel roads, that go through the fields. You get a very different perspective of this beautiful country by taking these backroads. Have a try!