It depends on what ever process you are comfortable with in the planning stage. We like to get the airline first. This becomes the first LOCK IN as to the dates. Then there is a certain set of hotels we like. These are mostly pensioner, small, family run hotels. If one is booked up, we just move on to the next. There are many more rooms available at any one time then there are airline flights. As long as the hotel has what we need; Location, Price, Good Reviews, Private Bath and Breakfast, and possibly parking, we are not picky since we are only at the hotel to store our stuff and crash after long days of being out in Italy. That becomes the Second Lock, or sign off. Then we do a day by day, hour by hour, itinerary of the things we want to see and experience. I always want at least one day on a motorcycle, and my wife wants at least one day totally dedicated to shopping. And at least two days are completely open to be planned while we are there. Then of course, that well planned itinerary gets adjusted as we go along depending on the weather or some other much more interesting site or event we didn't know about.