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Which Hilltown for one night?

My husband and I will be spending two days in Florence and before heading to Rome for 3 days, we would like to stay in a Tuscany Hilltown for one day and night. We want to experience a smaller town for a night other than the big towns we will be experiencing of Venice, Florence and Rome. Any recommendations that would be easy to get to from Florence and somewhat on the way to Rome? Any thoughts on San Gimignano vs. Volterra vs. Assisi vs. Siena? Open to others...

Posted by
1994 posts

Depends on your interests. My choice would be Assisi (which is actually in Umbria, not Tuscany). I love the combination of hill town and truly superb art. And it's an easy stop by train about half way between Florence and Rome. Another possibility, a little further afield is Orvieto, which is about an hour north of Rome.

Posted by
10 posts

Thank you for your response. I should have stated that we are traveling by either train or bus. Tough to choose...

Posted by
1898 posts

Assisi is wonderful, it's a train ride, then a bus ride to get to the hilltop town. Another option you will hear is Orvieto. It's right on the train line from Florence to Rome. To get to the town, you simple take the funicular up the hill - right across from the train station. For ease of travel, Orvieto would be easiest, just on and off the train at the town (with the funicular ride of course) Assisi is larger and has some wonderful places to eat, but not the view you get from Orvieto! Siena is not a small town, but is wonderful. You don't get that true hilltop town feel in Siena (IMO) It's a bus ride from Florence for ease. San Gimignano and Volterra are both amazing, but kind of off course and only accessible via bus. For ease of travel, something that is served by a train would save you lots of travel time.

Posted by
10 posts

We both agree that we would like to see Assisi. Do you think a stop in Cortona for a few hours would be worthwhile or should we just focus on Assisi?

Posted by
1658 posts

We loved Cortona. Certainly worth the stop. Follow RS walking tour to the top of the town, and the view can't be beat. There's easy parking as you drive up the hill on the right (free), then you walk to an escalator end end up at Via National, if memory serves me right. It's only about 15 minutes off A1 so easy to get to.

Posted by
3580 posts

Arezzo is on a train line from Florence to Rome. It is walkable from the train station to the top of the hill. Arezzo has a Roman arena with accompanying museum, a cathedral, and other sites of interest. The movie "Life is Beautiful" was filmed there.

Posted by
12315 posts

Orvieto was a pleasant surprise and very convenient between Rome and Florence. I like San Gimignano as a day stop but would choose Volterra for the night. I like Siena a lot, but haven't yet been to Assisi so can't give you an opinion on one versus the other.