Yeah. I've done it.
I would recommend flying into Milan, then taking a train to La Spezia. From there, you can pretty much ride south almost all the way down the coast. If you do it slowly, you can stop at some of the hostels along the coast and enjoy staying at beautiful hostels right along the ocean. Then, you can either ride south to Livornio, or you can swing inland and head to Pisa, and from Pisa, you can head into Florence, then take the train back from Florence to Milan and fly home from Milan.