Spreading ourselves too thin in Tuscany?

Remember that 2 nights equals one full day, etc. If I'm counting correctly you plan 4 nights in Siena, which is 3 days. I think you're trying to cram too much in. Instead of spending several half days in Siena, and a hill town, why not devote a full day to Siena. The other days I think a good rule of thumb is 2 hill towns per day. You might be able to squeeze in a 3rd town if they are in close proximity. You would also be in Siena in the evenings after you return from your touring for the day. I know the temptation is to fit in as much as you possibly can, but take time to enjoy being there. If you have a GPS it's easy to wander down unknown roads without worrying about getting lost. Do some research and narrow it down to the towns and areas you want to see the most.

Another option is to stay in Assisi rather than Orvieto. I personally love both places but believe there is more to see in Assisi. Orvieto has a more dramatic cathedral and there are also underground tours which are very enjoyable. Assisi also has a wonderful cathedral and the views are amazing. I had a great time just walking around the streets in Assisi. Whichever city you decide to stay in before Siena, I would not want to leave too early the next day. By time you pick up your luggage at the airport, travel to Orvieto, get to your hotel and drop off your luggage I would bet it will be later in the day than you plan. Things usually do not go exactly as planned. If there is a hold up of some kind you will not have too much time in Orvieto (or Assisi) that evening and may crash early from jetlag. I would want to have much of the next day for siteseeing before moving on.

Wednesday: land at what time? Sometimes it takes longer than you think from airplane touch down to the time you actually arrive at Roma Termini to get your train for Orvieto, that is especially true if you check luggage and you have to wait for it at the carousel when in Italy is "colazione" time and the baggage handlers are on a cappuccino and brioscia break. You are staying several nights in Siena. Different strokes for different folks but 3 or 4 nights in Siena is a hell of a long time to see Siena. Are you practicing on a horse to race at the next Palio or something? I know you'd like to take day trips, but I used to visit Montepulciano, Pienza, Montalcino and San Galgano in one Sunday and I was driving from Florence. There is nothing wrong with day tripping Assisi from Siena. It's all freeway and you can get there in way less than 2 hours. I know people who commute longer on a daily basis here in California. You can spend a night in Assisi if out like. It's nice but sometimes the checking in/unpack/repack/check out/checking again etc takes longer than driving from Siena to Assisi. I generally prefer to day trip rather than changing hotels too often for that reason.

Sharon, I can recommend a hotel in Siena if you decide to base there (my friends and I did that two summers ago and made day trips every day, usually two hill towns per day): Hotel Minerva. It's outside one of the main gates to the city, has on-site covered parking, and is convenient enough to get to the highways out of town. We based ourselves in Assisi for the second week of our trip. You can get to Assisi easily as a daytrip, park at the garage at Piazza Matteoti and your day will be downhill toward the Basilica instead of uphill (you can take a bus or taxi back to the garage if you don't want to walk). I spent several days in Orvieto, but one night is a good idea after all the traveling you'll do to get there. Roberto's idea of seeing 3 towns in one day is doable if they are in close proximity, but Roberto is fluent in Italian; if you're not, everything you do might take a little more time (I was the speaker for our group of 3). Also keep in mind that if you plan to have a nice meal (with great Tuscan wine) at a restaurant, it can take a couple of hours.

I can recommend a fantastic Agriturismo in Siena. If you would like information about it send me a Private Message.

I appreciate everyone's advice and will just have to prioritize the sights we want to see. From what Andrea, Dina and Zoe have to say, it sounds like the consensus is it may take longer to travel places so I would hate to cram too much in and then be disappointed because we are rushing...hate rushing!! The time spent in Siena is only a base, but I like your sense of humor Roberto! We would spend evenings there and of course part of one day exploring the city, but the rest of the time would be driving out of the city to different hill towns. We already have booked a room and we have parking so we need to stick with that. Their cancellation policy would probably allow us to shorten our stay by one night without penalty. So....that is where Assisi comes into play. Don't want to be over analyzing this but with a little revision, what do you all think of this itinerary. Wednesday : Arrive Rome 8:50 AM. (only have carry-on bags) Train to Orvieto. Spend the afternoon, evening and spend the night. Thursday: See more of Orvieto if desired, drive to Civita. Drive to Assisi, see the sights, wander the town in the evening and enjoy a wonderful dinner and spend the night. Have picked all hotels from RS book and reviews. Friday: See more of Assisi if we want to Drive to Spello (worth it with this schedule?) Head to Siena and check in. Enjoy Siena mid/late-afternoon and evening. Saturday : Stay in Siena & day trip Montepulciano, Pienza, and Montalcino. Sunday: See more of Siena if wanted and/or day trip to Chianti area. Monday: Leave Siena and see Volterra on way to La Spezia to turn car in . I just love the travel tips form those who have experienced it, so thanks for putting up with me!
Sharon

Sharon, your trip is like an interesting mosaic. I loved Spello, it's only about 7km from Assisi. There's a public parking area just down the hill from the main town, and there are recently discovered Roman mosaic pavements there that show the wine and food industry in the area about 1700 years ago!

I'm only in the planning stages of a trip to Tuscany so obviously I don't know much and everyone's style is different but..... I figure one hill town in a day is plenty so I have time to sit and have a long meal, sample local wines and relax. I'm less interested in checking things off my list as opposed to soaking it in a little. Even then I know I'm just scratching the surface. Sometimes less is more.

You all are right...I need to quit adding so many destinations to our itinerary. We want to soak it all in wherever we go, so I am going to drop Assisi from our trip, realizing we can't see everything, and hope to go back another time and see more in that area! Thanks for the helpful words everyone!
Sharon