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Old 09-20-16, 03:51 AM
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It sounds like a lot of fun. In the past, Italian trains were relatively cheap, and you might choose to do a mix of train + cycling. I believe the area around Siena was rather mountainous.

The Apennine mountain range runs through central Italy, and you may end up crossing it to get between North and South. I remember crossing the Abetone pass, which had a lot of intense up and downs.

Fortunately, with electronic route planning, you should be able to get an estimate of hills and elevations to your preference.

English is widely spoken in the more tourist areas (Rome, Pisa, Florence, etc). Some knowledge of Italian will be helpful if you stray from the beaten path.
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