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Itinerary help in Tuscany!

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My friend and I (both of us are foodies and wine lovers) are planning on extending our trip of a week cooking in Umbria to explore the Tuscan region. We'll be checking in to a hotel in Greve in Chianti for 2 nights on September 13, to enjoy the Chianti Classico Wine Festival. We will be in Tuscany until 19 September. We leave out of Rome that day at 2:45 pm. So far that is the only plan we've made. While in Tuscany we would like to tour some wineries, go on a Hot Air Balloon ride, explore San Gimignano, visit Sienna, check out the many Renaissance museums and churches, and hike the Cinque Terre. I am overwhelmed by all of the wonderful options and need help in planning our itinerary. Do we need a car in the region, or should we book day tours instead of driving ourselves? What order should we consider travelling to these towns? I've read so much about Vinci, Cortona, Montepulciano, and Montalcino - too many places, too little time. Which of these towns would you recommend we spend time visiting? We want to see as much as possible without spreading ourselves too thin. Our budget leaves room for private tours. Any information or guidance you can lend is greatly appreciated, such as where to stay, where to eat, which wineries we should visit, where to explore, and in what order. Also, we are not planning on going to Florence or Pisa this trip since we've both been there already.Thanks in advance!

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