I haven't read all the postings, so apologies if this has been mentioned... but consider _riding_ to Gaiole from Florence or Pisa. Take a a week or more and really see Tuscany! When we did it ('05), it wasn't for L'Eroica, but we did go through Chianti not too far from Gaiole. Laurie and I were privileged to go with Glenn and Nancy Erickson of Erickson Cycle Tours. It wasn't a commercial trip -- it was just friends and family -- it was actually their wedding party! As in, they got married mid-way on the trip. But we used their standard Tuscany route and hotels/restaurants.
We didn't ride right out of Florence, which I imagine might be a bit ugly. We got taken by van to a little hill town about halfway between Florence and Pisa, called Montopoli. Some other guests flew into Pisa; either airport is about as convenient. We stayed in the Quattro Gigli (Four Lilies) which was a lovely introduction to Tuscany - ancient charm, great food and wine, hospitality and views. The riding was incredible right from the first pedal stroke out of Montopoli. (When you stay in hill towns, mornings start out going downhill.) First night on the road was spent in Volterra. I sorta forget where we went after that; anyway you might want to find your own route/hotels, because we took almost two weeks to get to the heart of Chianti by our meandering route that included the Maremma, Montalcino, Montepulciano, Cortona, a little Umbria.... nothing resembling a direct route to Gaiole. On the plus side for this corkscrew route, you'd ride yourself into shape and have a fantastic experience before L'Eroica.
I admit that having the van carry our gear was pretty nice, you'd have to be a hardier sort to carry it all with you on the bike unsupported. Maybe hook up with a commercial trip? I can definitely recommend Erickson, they really know how to enjoy Tuscany -- and where to eat! Man, some of those meals still bring back happy memories. I didn't know food could be so good. Erickson's Tuscany trip is usually right about that time of year too, though they don't seem to have dates for 2011 on their website yet. Disclaimer, I'm an old friend of Glenn and Nancy Erickson, so I am biased.
Mark Bulgier
Seattle, WA
USA