We plan to fly into Milan on March 21 and out of Rome on March 27. We really want the freedom of not having a schedule other than getting ourselves to the airport on time. Is this the most naive plan or do you think its workable?
I seldom make reservations anywhere that time of year and never have trouble. Unless there's a festival some place you're going? BUT, you're getting real close to holy week, I think. Rome might be crowded.
You don't need them, but you might consider a reservation for the first night. You probably already know where you want to go when you arrive. For me, I find it helpful to have the directions and map for where I will be sleeping that night.
I agree with Ed that you also might also want to reserve in Rome (at least for your last night if you have an early morning flight).
Everybody has his/her own style. If I'm driving, I like having my stuff in the trunk and being free to stop when and where I want.
But if I'm going by train and need to pull my suitcase along, I'd rather check out hotel recommendations and prices ahead of time and know my route. Especially with such a short trip, I wouldn't want to spend extra hours searching for lodgings - or losing hours waiting for trains or buses.
Palm Sunday is the 28th, so I'm sure it will be busy.