hill town lodging

We are planning a trip to italy in mid May. We will be driving from Florence to Orvieto over 3 days, with one night in Volterra and one night in Orvieto for sure. Third night unclear.
The question: Is it best to book ahead or just look once in town? If ahead, how far? Months like now, weeks or the day before? We will be a party of four. Any advice or tips would be appreciated.

Posted by Michael
Seattle, WA, USA
6726 posts

Why not spend the extra night in either Volterra or Orvieto? That way you'll be able to experience the town in a much more enjoyable way. And I would book lodging now, esp. since you'll presumably be needing two rooms.

Posted by Zoe
Toledo, Ohio, US
7334 posts

I just booked my last reservation in Italy for May, I wouldn't wait much longer if you need two rooms. You can try booking.com for photos and reviews from guests who have stayed recently. If you prefer to wait, you can sign up for last-minute alerts. In Orvieto, Hotel Virgilio is right on the main piazza.