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Help with solo Tuscany trip please!

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I am turning 60 very soon and I am dreaming of a trip to Tuscany. My usual travel partner is unavailable and I am considering a solo trip. I have traveled solo before to Paris and enjoyed it very much. Tuscany will be tougher since driving solo will be involved and that worries me. I have driven in Italy but not alone. Here are my thoughts. Please jump in with yours.

I would land in Rome and train to Chiusi to pick up a rental car. I very much want to stay in the area around Pienza, Montalcino and Montepulciano. That way I can see several towns without driving very far each day. I do not plan to drive at night.

I really would appreciate your help with a place to stay. I would prefer an agriturismo with great views and plenty of room to walk and enjoy the scenery. I plan on spending some time just relaxing and reading in a beautiful setting. I would like the option of dinner since I will not be out driving at night. I can spend around E150 per night for at least 5 nights before dropping the car back in Chiusi and train back to Rome. This will take place in May or June of 2014 so I need to get to work on this really soon.

Thanks for helping. I look forward to your ideas..

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