Join Date: Sep 2004
Location: Frisco, CO
Bikes: '93 Bridgestone MB-3, '88 Marinoni road bike, '00 Marinoni Piuma, '01 Riv A/R
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has an excellent selection of maps of Italy, I used the TCI maps on a tour through Tuscany & Umbria last year in May. The first day of my tour was 80 km/50 miles from Florence to just north of Siena, if you were to push on to the train station and catch a train home you would probably cover 60 miles or a touch more. I left Florence and headed south to Impruneta, then went east to the SP222 and followed that road south to Siena. Very pretty ride, no traffic problems, and you should have no problem getting your bike on a train back to Florence. Just outside Greve in Chianti is a little hilltop village called Montefioralle, it's a really pretty little hill town that's worth the detour and the stiff climb. If you can find a copy of Lonely Planet's Cycling Guide to Italy, this ride roughly follows one of the tours in that book.
If you can spare the time, overnight in Siena and spend the morning (before about 10 AM) wandering through the old town. The tour buses full of day-trippers roll in around 10-11 AM, but before then the old part of town is quite empty, and it looks a lot like it did hundreds of years ago, only cleaner.