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Best 5-day hill towns in Tuscany/ Umbria

Part of my October Italy travels will include a 10-day stretch and a 2-day visit that I want to spend in Tuscany or Umbria. I'm thinking of dividing the 10 days into two 5-day stays, and I want to stay in towns that have easy train or bus access to other towns. I am open to suggestions, but think the three towns for either 2 or 5 days might be 1-Siena, where I've been before but want to connect to San Gimignano andVolterra, 2-Orvieto, and 3-Cortona. Which one would be best for 2 days and which ones are best for 5 days? I think Cortona might be one of the 5-day stays. The 2 days would be on the way from Venice to Rome. I will probably skip Florence this trip since I've been there before.
Thanks,
Bev

Posted by
16243 posts

Since you rely on trains and buses you should stay in Florence for your Tuscany exploring. Florence is the transportation hub in the region.
San Gimignano and Volterra are somewhat in between Florence and Siena. The former is easily reached from the Poggibonsi station (along the Florence Siena rail line). The latter will require a bus to Colle Val D'Elsa then another bus from Colle to Volterra (I don't think there are direct buses from either Florence or Siena). Volterra is actually also easily reached by bus from Pontedera, along the Florence-Pisa rail line (probably more frequently and faster).
Cortona is much more easily reached from Florence than from Siena.
Orvieto is an easy trip from Rome.

Posted by
715 posts

Umbria, Perugia (do not under estimate this city, it is beautiful), Assisi, Spello, Gubbio, Spoleto, Montefalco, Bevagna. I would use Assisi as a base as you can easily train or bus to the others. Well Gubbio is a bit of a stretch to get to but well worth it. Spello, Montefalco and Bevagna can be day, or have day visits.

Posted by
11613 posts

If you've already been to Florence, you could base in Siena which has convenient bus service to the towns in southern Tuscany. For Umbria, Perugia has the best transportation connections, but personally I prefer Assisi. I spent two days in Cortona a couple of years ago and loved it. You might add Todi to the list of Umbrian towns, not as a transportation base, though.