In 2014 after I finished the Camino Francis I promised myself to continue to walk and explore at least two weeks per year. This May I am going to walk part of the Via Francigena in Italy, from San Gimignano to Rome, 265 km. The plan includes the flight RT from Lisbon to Florence and approximately 14 days of walking. The web site for the Via Francigena has all the details you need to begin to plan. Starting with the .gpx files for each leg you can map out your plan using google maps. I decided to skip a long and very difficult leg #35 to save my knees! Planning one of these walks is part of the fun of doing them.
Our plan is now set, lodging has been reserved and trains to San Gimignano and Rome to Florence are booked. We decided not to wing it for two reasons, 1) no reason to suffer after a long walk and 2) enjoy the Tuscan countryside in style in interesting historic places! All our reservations were booked using Booking.com.
I have found a spreadsheet of details to be helpful in managing all the details, I save it on Google Drive so I can retrieve it anywhere.
Also, the app for the Francigena for iPhone is a useful tool, the link can be found on the official site or on the App store for free.
I ordered my credential to make it easier once we arrive. There is also a book in English you can order with all the details. Note that this walk actually begins in England, so the book is a heavy load to carry.