Is it possible to hire a driver to get us from Florence to Montepulciano? We plan on spending 3 nights in Florence and would like to spend a couple of nights further south. Am planning on going to Positano after that. What would be the most direct route. Is it also possible to hire drivers to go to Siena or Cortona from Montepulciano? My daughter and I feel a little uncomfortable hiring our own car and going it on our own. Thank you for any information you can give me.
You can hire a driver to take you to Siberia and back if you want. The issue is price.
Search for Noleggio Con Conducente (or NCC) followed by the name of the city, and Google will give you plenty of hits.
There is no need to either rent a car or hire a driver. You can take the train from Florence to Montepulciano, from Montepulciano to Siena, and from Montepulciano to Cortona. Each route requires making connections, but they aren't complicated. To get from Montepulciano to Positano you first will have to take Trenitalia trains to Naples (connections required), then a Circumvesuviana commuter train to Sorrento, and finally a SITA bus to Positano.