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Tuscany by car All the backroads

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We plan to tour Tuscany (from Montepulciano) for at least 6 days in Spring of 2014 We are only two adults 60 plus and have toured the big cities previously (Rome, Pisa, Florence ,Venice etc) Can anyone give a iternery to see the most stunning mountain towns ? Also - will it be possible to not pre-book but just arrive and look for a place to sleep?

Thanks
Marego

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