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Tuscany Itinerary w/ Car Help

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I am planning to spend 7 full days in Tuscany in September 2014. I'm thinking of splitting my time with stays in Southern and Northern Tuscany to limit drive times in the area -- trade off is moving to different lodging every two days. Interested in your commentary about the following itinerary and whether I should consider a one or two bases for the week, if so what would you recommend. Our interest is in seeing the Tuscan Landscape, visiting a Chianti Vineyard (Castello D Verrazano near Grieve?) plus the sites of Florence. Not sure if I'm cramming too much into the seven days given drive times. Thanks for your recommendations.

Day 1: Drive from Rome to Montepulciano arrive around 3 p.m
Day 2: Drive around Val D' Orcia area (Montalcino, Pienza), stay in Montepuliciano
Day 3: Drive to San Gimignano area for day, stay in Siena
Day 4: Tour Chianti area (Radda to Grieve) from Siena
Day 5; Morning in Siena, drive to Florence
Day 6: Florence
Day 7: Florence

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