My wife and I are planning to depart from Rome, visit the hill towns of Orvieto, Assisi, and Siena over a period of four days, and then end up in Florence. We will be taking public transportation. We are looking for advice on the best way (train or bus) and the best order (for transportation schedule or other reasons) to visit the hill towns. We will be traveling in October. Do transportation schedules make a particular order of the hill towns easier? Are there any things about bus or train schedules that we need to be aware of? Are train or bus reservations necessary or advisable? Also, any suggestions about places to stay in the hill towns would be appreciated. Thanks.
Probably best to go Orevieto to Assisi to Florence to Siena. Assisi to Florence is a direct train. Florence to Siena is more direct by bus and takes you to the upper town. You could do this as a day trip from Florence.
You can get to all the cities you mention by train or bus. Rome to Florence would be the only train ticket that would benefit from a reservation, but that's not the best itinerary.
You could visit Orvieto as a daytrip from Rome and Siena as a daytrip from Florence, easily done by bus or train. I prefer staying overnight in these cities, they are very different when the day trippers are gone, but October should be less touristy than the summer months.
The train stations in Assisi, Siena and Orvieto are in fact down the hill from the towns, but buses (and the funivia in Orvieto) are frequent. Getting to Siena's city center can be a little confusing, so a bus there might be more convenient, or you can take a taxi.
In Orvieto I like Hotel Virgilio on the Piazza Duomo or Hotel Duomo around the corner. In Assisi I have enjoyed hotel Hotel Il Palazzo. Still looking for a great place in Siena.
I recently did something similar: Florence to Assisi to Orvieto to Rome - all by train. Your route would be the opposite, then take the bus from Florence to Siena. Use the Trenitalia website for train schedules.
When you arrive in Orvieto, you take the funicular from the train station up the hill. Then you can wait for the minibus to the center or walk (depending on your luggage, probably) to your hotel. There are also taxis available. The town center is pretty flat. (There's no luggage storage at the train station.)
From Orvieto to Siena, you'll have to change trains, but it's simple. When you arrive in Siena, you can leave your bags at the train station and just take an overnight bag up the hill. There is a bus that makes several stops in the town center. Assisi is very hilly, lots of steps and steep inclines, so you won't want to schlep your bags.
On Zoe's recommendation, I stayed at Hotel Duomo in Orvieto and really liked it. I saved a bit by staying in the annexe, which was an easy walk to the hotel for breakfast, or anything else, and the wifi worked well. I met a couple there who splurged on a junior suite and loved it. Don't be enticed by the "view of the Duomo" - it's a side view, nothing extraordinary.
In Assisi, I stayed at Hotel La Fortezza. The only real negative was no shower curtain in the bathroom, so it got pretty wet. Positives - good wifi, nice view, breakfast on the roof.