You might consider extending your time south rather than look for a place "in between" Orvieto and Volterra. Tarquinia is very underrated, and for Etruscan lovers, Civitella Castellina is a real joy. Maybe you could look into a stay somewhere in between (around Vetralla or Sutri) for a very untouristy taste of Italy. You'd also be within striking distance of the sea.

With a very young child in tow, I would not want to be in the steep hilltowns, including Siena.

If you want to move north, even though you spent extensive time around Florence, you might consider Fiesole, one of the original Etruscan league cities. There are pretty apartments up there in the olive groves and villa gardens and walks, but the committed sightseers in your group would have the short bus ride to Florence. You could also visit Arezzo, another of the original 12 Etruscan league cities.

Take a look at this sweet place near Sutri:

http://www.agriturismomontefosco.it/...switchlang=eng

Sorry, I'm not sure that's the best link. Try this:

http://www.agriturismomontefosco.it/...ismo-lazio.php

The farm grows hazlenuts, and the area is rich with Etruscan sights, from Tarquinia to Civita Castellina, and Sutri itself. Plus, there are two lakes nearby (Bracciano and Bolsena)

http://www.agriturismomontefosco.it/...e-dintorni.php

And here is a pretty place on the shores of Lago di Vico, but still very close to many sights of fascination, Etruscan and otherwise:

http://www.agriturismolavita.it/art-...azio-italy.php

Or something super-family friendly on the shores of Lago di Vico

http://www.cottagestocastles.com/Ita...-CONCETTA.aspx

But if you want to base yourself near Siena nonetheless, this is THE place (actually, one of the finest accomodations all over Italy): www.quattrotorra.it
As far as driving into Siena, there's no way of doing so; you have to leave your car outside the walls (1 km from Quattro Torra), and take a bus.

Many thanks, zeppole and franco. Oh my goodness, I have poured over your many posts on this board over the years and you both have been so helpful.

I'm still looking into all the advice on this thread. My researching takes a bit longer these days with my sweet little helper ;-).

I'm definitely starting to realize how truly vast Tuscany/Umbria is... yes, it is a large area geographically, but the concentration of amazing things to see is quite overwhelming. I foresee many return trips in our future because I am realizing there is *no way* we can see everything in this trip (nor would it be any fun to try!). Anyway, thank you again for all the help!

We stayed several days at Palazzo Ravizza in Siena last October. The hotel is just barely inside the city walls and has its own parking lot with direct access to the hotel via an outdoor staircase. There is a good-sized garden (shown on the hotel's website) that faces mostly west, so it's a nice place at the end of the day as the sun is going down. Although you're 'inside' Siena, the garden side of the Ravizza feels like you're 'outside' the town. My only caveat to recommending this hotel is forget their restaurant suggestions. We found much better spots on our own.

http://www.palazzoravizza.it/

oh, hi franco! I'm in rome.

zeppole, I'm green with envy!!!!!!! How long?

With a very young child in tow, I would not want to be in the steep hilltowns, including Siena.>>

orbetello and its environs are blessedly flat and very good for recreational cycling.

BTW - the soon to be notorious isola di giglio where the cruise chip has gone aground is just off this bit of the coast - sadly 3 confirmed dead and 70+ still missing.

Just a week, and the weather is ideal for marching all over the place.

Zeppole, I too am green with envy :). We love Rome any time of year, but especially when it is sunny, cool, and crisp outside.

I'm still continuing to research the middle portion of our trip. As my folks have a separate rental car, we may consider splitting up for 3-4 days in the middle of this trip to accomodate different interests. We've done long international trips before together as a family and get along quite well, but a little break mid-trip might not be an unwelcome thing.