Umbria or Tuscany?

You can't have it both ways. Close to Florence will be much nicer than close to Rome. Orvieto might be a reasonable compromise. But you have to ask how many suburban and rural Americanskis will spend the time and effort to sit repeatedly on public transportation for a looooong daytrip?

The number of cars, phones, and drivers is also relevant to the decision. I mean to include shuttling people to the train station. Be sure to search this board for data on rentals, insurance, IDPs, ZTLs, and so on.

Kind of figured this would be the case.. I agree Florence area would be nicer.. My thought would be for those who want to go to Rome make a several day trip as they will have a month.. Florence to Rome can't be that long a ride on a high-speed line.

Firenze to Roma is less than two hours, as I recall. But you probably won't be in Firenze, if I understand your plan, so add time each way.

I would stay near Florence, it is only 1 1/2 hours to Rome from Florence. You'll be closer to many hill towns than you would be near Rome and you'll be in the heart of Chianti wine counrty.

Sixteen people. For a month. Do they all plan to be in the same place all month ? Most people who come to these boards would be planning to visit 10-20 places in a month. Sounds like a great idea to have a long-term base for people to use for their own small-group trips; hope you're not the one responsible for logistics (transportation, coordination, communication, cooking)

We recently stayed outside Siena and outside Orvieto -- both were great.

We have been part of a similar size group 3 times, though not as long as for a month. I believe the longest stretch was 2 weeks. We had several cars among us. What worked well was that each evening there would be a discussion of who wanted to go where the next day, with the desires of the car renters being given priority. We'd then sort ourselves out into car groups. No one even considered the possibility that we'd all do the same thing. Sometimes some of the cars were used to drop people at the nearest train station.
It's important to get a place with some attractive amenities, like a pool. That way people who want a break from sight-seeing will have something to do.
One thing we learned after the 1st experience is that it's important to scope out how long it takes to get from your residence to a main road. On a map the distance looked short; and, as the crow flies, it was. However, what we didn't know was that there was a private, unpaved road after the turn from the highway, that was so hilly and rough that it had to be done in 1st gear most of the way. Then, the paved section took 20 minutes because of being 2 - lane, hilly and winding. Altogether, 40 minutes to reach a major road. Doing that 40 minutes twice a day, every day, got old really fast.

Both regions are wonderful, but we would recommend Tuscany for all of the reasons you've heard...Florence, Siena, Pisa, Chianti, cooking lessons, vineyards, truffle hunting (depending on the season), proximity to Emilia-Romagna and Cinque Terre for side trips, etc., etc.
As you've heard from others, train to Rome if necessary. Great service, frequent schedules. Have fun!

Just thought on the idea of day trips to Rome from Florence: It will get expensive fast with roundtrip train tickets. If you buy in advance and can commit to the schedule of an advance, non-refundable ticket, it can be quite inexpensive, but spur-of-the-moment has a price. Perhaps some people will consider a two night stay in Rome to as an alternative to the back-and-forth. Ditto Venice.

Steve,

I love the area around Pienza - the landscape is breathtaking .

Kathy

If you want to be around Italians, Umbria. It's a little wilder, less cynically catering to the tourist trade. Plus, we pronounce our "c," with apologies to Roberto. Costs less, too.