I am going to Italy May 6, returning May 24. Round trip to Milan, with the first leg from DFW connecting at JFK.
3 nights in Milan, where I will see a concert at La Scala, The Last Supper, and the cathedral, among other things.
Take the train to Monterosso al Mare and spend three night in Cinque Terre.
Next, take the train to Florence to pick up a rental car, and probably see San Gimignano on my way to Siena, where I will spend two nights.
From there, I drive to Montepulciano for three nights exploring the Val d'Orcia and surrounding towns.
I return the rental car to Florence and spend two nights there. This is the only place on my itinerary that I've previously visited, and, having seen David at the Academia last time, I will skip that in favor of the Uffizzi and the Pittii Palace.
I will take the train to my final base, Bologna, for three nights in the food capital of Italy. I may take a tour of a cheese factory and basalmic vinegar acetaia around Modena, but will definitely stop in Modena on my way back to Milan to see the Enzo Ferrari museum and the city center.
Final night will be at the airport Sheraton because I have a 7:00 am connecting flight to Heathrow.