My response to David.
You said it has been over 20 years since you have been to Italy. Tuscany, and much of Italy, has changed since then. We traveled a lot to Italy in the mid-90s and we see a big difference now. The main cities – Venice, Florence, Rome – are very crowded. Not just Europeans, Brits and Americans, but apparently the Chinese are traveling in big numbers. Plus the whole cruise ship thing – where the boats unload all their people into a city for a day.
Tuscany, and parts of Umbria, are very upscale now. You don’t find falling apart villages – everything has been renovated. I assume Chianti is like this, but we have not been there in 15 years. My favorite part of Tuscany is the Val d’Orcia, south of Siena, with the towns of Montepulciano, Pienza, Montalcino. We spent a lot of time there 20 years ago, and returned the year before last. I still love the area, but there are more tourists. The piazzas are not full of old men talking, but full of more prosperous cafes. That old Italy is still there and I recommend you go to Tuscany, but perhaps for a week instead of a month – so you can see what it is like now.
For Tuscany I have three recommendations.
Sant Antonio:
http://www.santantonio.it/
This is an olive growing estate outside of Montepulciano. We spent a week here the year before last. Many of my travel friends go there every year. It is run by Nico and his wife. They are Italian and they run the place well. It is an building that was in Nico’s family and he turned it into 12 apartments over 10 years ago. Nicely furnished, very comfortable. He lives close by and has full time staff who are always around if you need them. You need a car. It is just a few minutes to Montepulciano.
Read my review here:
http://www.sloweurope.com/community...nt-antonio-apartment-in-countryside-1bed.716/
And other reviews:
http://www.sloweurope.com/reviews/221/Sant-Antonio/
Cretaiole:
http://www.cretaiole.it/
I have not stayed there but everyone loves it. A farm near Pienza. Reviews here:
http://www.sloweurope.com/reviews/363/Agriturismo-Cretaiole/ (they flooded my site with reviews)
And here:
http://www.sloweurope.com/community...pienza-agriturismo-cretaiole-is-amazing.1082/
TuscanHouse:
http://www.tuscanhouse.com/
A very good small agency that offers very nice houses in southern Tuscany. The area south of the Val d’Orcia is more spread out that the central Tuscany area the first two places are in and is not as touristed.
Read reviews here:
http://www.sloweurope.com/reviews/327/TuscanHouse/
I keep a list of interesting vacation rental (holiday rental) resources on my website:
http://www.sloweurope.com/vacationrentals/italy/tuscany/
While I think Tuscany is a bit posh and touristy, I still love it. The extra tourism brings great restaurants and shops and delis.
For Umbria I have one recommendation:
Umbria is less touristed in some places, but sweet small towns like Montefalco and Bevagna are much more upscale than they used to be. We recently spent a week in Spoleto, a town in southern Umbria. It is a very good town, good walking in the hills behind the town, great restaurants.
Umbria Holiday Rentals:
http://www.umbriaholidayrentals.com/
This agency has very good apartments right in Spoleto.
Read my review here:
http://www.sloweurope.com/community/threads/umbria-spoleto-2bed-2bath-apartment-in-the-center.1191/