TJinSOMA

We are heading to Cortona in May for a week in a villa with friends. We will be driving from Florence to Cortona and we're interested in peoples thoughts on the "best" one stop between the two towns? We've done Chianti before on trips but just curious on a can't miss stop. The two that caught my eye were Castello di Brolio (but it sounds a little touristy and I saw the word tour bus in several reviews) and Castellina in Chianti.

We are also going to do a day trip from Cortona to the Montepulciano area and curious on any can't miss stops or wineries around there? We tend to like great wine but prefer smaller mom and pop producers. We live in Napa Valley and have always found the small family owned producers tend to be much more fun (and better wine) than the large glitzy spots.

Jean

I would drive the Strada Chiantigiana (SR/SS 222) south to Castellina and then turn east to Cortona, stopping wherever the mood strikes. Tiny Panzano is charming but may come too early in your drive for a meal stop. We liked Castellina and Radda and have had nice lunches in both towns.

A suggestion for your Montepulciano day is to make a circle drive that takes you to Abbazia di Monte Oliveto Maggiore near Asciano on your way to or from Montepulciano. (This circle would also take you to Pienza and San Quirico.) You would need to time your arrival carefully as the entire abbey and its grounds are closed from noon to 3:00p for lunch and prayers. There is a café with a nice terrace near the entrance.

http://www.monteolivetomaggiore.it/home.html

There is a wine tasting room in Montepulciano. Most area wineries are not open for drive-by/drop-in visitors, so you should do some research in advance and make reservations wherever you'd like to stop.

TJinSOMA

Much appreciated Jean. We have done Radda in the past and enjoyed so think we'll try Castellina (not worried about meal as think we may just have a late breakfast in Florence and then wait and have lunch in Cortona).

The Montepulciano loop sounds great as well.

kybourbon

If you like wine and loop as far as San Quirico, I would drive a tad further and visit Montalcino. Sample the Brunellos in the Fortezza or if you want a view, at Enoteca Osticcio.

In Montepulciano there are plenty of places to sample wines in town, but I think this vineyard is also within or just at the edge.

http://www.gattavecchi.it/wine-tasting-nobile.en.php