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One day car trip from Siena and back

I have a rental car for one day in Siena, a Thursday in late May. I want to take a day to get away from where a lot of tourists will be, see some of the countryside and some of the out-of-the-way villages and hill towns. So I've been looking at maps to try to plan some possibilities.

One trip I'm considering would be to Pienza via Monteroni d'Arbia and back via Trequanda and Asciano. According to Google maps, the driving time is 2.5 hours, so that should give me plenty of time to slow down, enjoy leisurely walks through the villages, and still get back to Siena before dark.

Does anyone know any of the small towns along that route? Can anyone suggest any detours? (I know I'm close to Montalcino and Montepulciano, which I might detour to, but I'm also interested in more out-of-the-way places.)

Thanks for any ideas.

Posted by
196 posts

Hi Lane,
I had the pleasure of renting a car about 6 years ago for one day(arrange your rental from the US). We left Siena and headed North up the SR2 toward Poggibonsi. East on the 429 into Chianti. If you love wine than this is a must. If you don't care for wine you will still love this area for it's beautiful hilltop towns. Memorable moments were the towns of Rada, Castellina in Chianti and a hilltop castle/winery which offers a private tour with a wine tasting. Just a note on wine tasting, It is best to inform the winemakers that you "intend" on buying wine and would like to taste. Buy at least one bottle of wine from them.... there is a huge misunderstanding between Italian wine makers and the foreign tasters... in the US is quite acceptable to wine taste without purchusing this is a major no no in Italy.... just a word of warning.