My wife and I are traveling to Radda in Chianti from October 2-7. On Sunday October 6 I will be doing the L'Eroica ride from Gaiole. Any suggestions of where to go other than Florence or Siena? Thanks!
Go David go! Doing the Eroica sounds wonderful and a great way to see Chianti! Plus, cyclists and apacionados really love this race and the white roads!
I'd actually love to go see it since I'm not a great cyclist, even if my husband keeps trying to convince me to try it more often... I just don't do hills well ;-).
Since you'll see a good amount of beautiful Chianti countryside around Gaiole on the Saturday, I'd propose to head in the opposite direction from Radda on the other days.
Definitely a full day in Florence and another in Siena. That leaves you another 2-3 full days, right?
I would suggest to do another day trip where you head to Volterra, stopping along the way in Colle Val d'Elsa.... and another full day trip where you go to San Gimignano in the morning, then in the afternoon head to Certaldo, passing back through Tavernelle Val di Pesa to get to San Donato in Poggio, stopping along the way to take photos and visit the medieval hilltop towns. If you get a chance, also stop in Castellina in Chianti and visit Panzano in Chianti... maybe you can do dinners there and not always stay in Radda in the evenings, to see these towns in the evening too.
Finally, if you do have the third full day (or in alternative to the other days in Chianti), I'd head to Arezzo - it is a beautiful town, not on many of the main itineraries in Tuscany but it is very charming, quiet and beautiful to discover. Make sure to go to see the frescoes in the Church of San Francesco by Piero della Francesca, the colors and scenes are breathtaking. Here's more on what to do on a day in Arezzo.