Oriveto - Siena - Florence --- How to spend time

Siena is a medium size city and imo doesn't have a countryside feel. If you want to visit Siena, I'd suggest staying 3 nights in Florence and doing Siena as a day trip. Smaller towns with a more countryside feel along the train line from Orvieto to Florence are Chiusi, Montepulciano and Cortona. All involve a bus ride from the train station, with Chiusi to Montepulciano being the longest (about a half hour). Montepulciano and Cortona are hill towns, same as Orvieto. Arezzo is another option, although it's going to have a city feel similar to Siena. The advantage is that you can walk into town from the Arezzo train station.

We just did something similar to what you are planning: 5 nights in Rome, then 3 nights in Florence and 2 nights in Siena. My suggestion would be that you spend all 3 nights in Florence. If you/your group are art lovers, the treasures in Florence would keep you busy for the duration and you would leave with the feeling that you didn't have nearly as much time as you would like. If you would rather spend a day outside of Florence, you could do a day trip to Siena or Fiesole, both of which are less than 1.5 hr away by bus (Fiesole is closer). I deduct that you are going to move on to other places after Toscana, by doing a day trip instead of spending a night in Siena, you save yourself the hassle of lugging all your stuff to Siena and back to Florence before moving on to the next spot (I assume you are taking trains?). Also, I encourage you to get up early to go to Siena before the crowd descends so you can experience the town in relative peace and quiet.

With all that said, both places are beautiful and full of interesting sites to see. So you can't do wrong no matter what you decide in the end. Just enjoy your trip.

Mei's response gave me another idea. Instead of staying in central Florence, stay in Fiesole. It's only 20 minutes from Piazza San Marco by bus #7, but it's fairly small with a countryside feel and often cooler temperatures. You would need to change buses at Piazza San Marco to get to the train station, or you could walk between them in about 15 minutes. If you stay in Fiesole, consider whether daily or weekly bus passes instead of individual tickets would save you money.

I would give priority to spending a night in Siena over spending a night in Orvieto.

Siena is a favorite city of mine. It is unique and deserves more time that one night, IMHO. I love Albergo Bernini for a hotel. It's close to most things and is in the Rooster contrada, I believe. Very close to a bus stop and steps from St. Catherine's church. Was awoken most mornings by bells from the church. The view from their terrace is gorgeous. Good restaurant on street behind the Bernini....I forget the name.

I would drop Orvieto and save it for another trip. I spent three nights there in 2008 and it was definitely two nights too many. The town closes at 9pm.

Siena is a great city, but I would spend the extra night in Florence. There is much to see here, which would easily use the extra day. One of our favorite nighttime activities is to sit on the steps near where the Uffizi and the Palazzo del Signora meet and listen to the street musicians. Florence has many top music schools and it draws many fine musicians from around the world. Listening to these upscale and talented musicians is, IMHO, a most pleasant evening activity.

Two years ago we spent five nights in Siena and thoroughly enjoyed the time. We stayed at the four star Hotel Athena inside the city walls. This is another city worthy of a visit on another trip.

Buon viaggio,

Because you don't have a car, I want to mention the possibility of daytrips from Florence. I hate changing hotels, but if I were stuck in a city, I would want it to be Florence rather than Siena. Even a 10-minute city (i.e. frequent all day) bus ride to Fiesole (an attraction in itself) puts you in a dramatically different place than Florence. It's an oversimplification, but chosing between Siena and Florence is making a choice (I mean, you might want one or the other) between Gothic and Renaissance period traces.

I agree that Orvieto is almost made for a daytrip, and doesn't fall under this newsboard's classification of "Must Sleep and See After The Evil Daytrippers Leave". That doesn't mean it isn't a lovely place, by the way. We liked it very much.