We are thinking of going with extended family to Tuscany/Umbria for a few weeks in May. I've chatted with a few people and done some research. I offer the state of what I know, and ask for help from experienced travellers for additional advice. If you've got tips like "We loved villa v, you have to go to x, you shouldn't go to y, when travelling with kids don't forget z..", please let me know. I plan on updating this blog entry as I get comments, then have a trip report blog entry after.
Travel Books and sites
I'm looking for travel books that provide context and say "if you have 7 days visit towns x,y,z and winery w". I've read the Rick Steeves Italy and Tuscany books and thought they were ok but not great. The Fodor's best-loved driving tours is great for detailed itineraries but no context. It has too much "You will pass through the town of Montefaldicano. On the right is the 12th century water tower that was built by the ghibbelines, then destroyed in the 14th century...". I've had the food and wine lovers guide to Tuscany recommended.
The Fodor's web site has 3/5/7 day itineraries
Villas
We are looking for 2, maybe 3 weeks in a villa. A villa on the border between Tuscany and Umbria called Fonte Pecciano has been recommended. This seems like a great location, but should we be further towards Firenze? Arts and Leisure Tours, TuscanyNow, RelaxInItaly, Interhome all seem to offer villas in our price range but there's so many I feel overwhelmed. Italy Traveller has a very short list of villas, more hotels. Interesting other villas: Calcione, near Sienna;
There are a few villa sites that exceed our budget: AbercrombieKent, YourTuscany has one exception in Casa Luana
Hotels
Some random hotels that I've looked at:
Montepulciano's Il Marzocco and Mueble il Riccio
Castiglione del Lago's Alla Corte del Sole
Cortona's Il Falconiere, which has a good little 6 day itinerary.
Relais et Chateaux always has pricey places..
Child considerations
So many things to think about and to look into. Do we rent or ship or buy car seats? What do italians do for baby formula? Where are the nearest hospitals if the kids get sick? Should we bring a portable crib? Obviously we'll have travel insurance, we are leaning towards RBC currently.
Itineraries
Our rough plan for the 2 weeks is to take day trips around the villa. The day trips we are thinking of: Firenze, Sienna, Cortona, Chianti valley (montepulciano/montalcino), Umbria (peruggia, assissi?), and a few just drive around and find enotecas, restaurants, etc. That's about the extent of our planning so far. I'd love to find local fairs, festivals, even special events to attend. Ideally, we'll avoid any wineries that are "industrial" and find wineries where we can have an enjoyable visit, preferably with the vintner. We've had wonderful experiences with the vintners in France and Australia, and we're hoping to have similar memories from Tuscany.
Other articles
Trip reports: A castle in Umbria and a villa in Tuscany talks about La Frassinaia and Castello di Sorbello, and has exactly the kind of details that I like.