We are planning our third trip to Italy for late April to mid-May in 2020. We will have 24 to 26 nights to experience what we hope to visit. This is the current tentative plan:
Days one-three: Fly to Rome and immediately train to Naples. Spend three or four nights in Naples, with day trip to Pompeii, Herculaneum, and maybe Capri. Want to visit the archeological museum, art museums, and churches. We are huge Caravaggio fans so we plan to find his few paintings that are in Naples.
Days four-seven: Travel to Amalfi coast and stay in Positano or Amalfi. Spend four nights here. Plan to hike the Path of the Gods and visit towns via ferries.
Days seven-ten: Travel to Florence and spend four nights. Florence is our favorite city and we can't imagine going to Italy without spending some time here.
Days ten-24: Here is where we are struggling the most. We want to focus on Umbria before returning for a few days in Rome and then fly home from Rome. These are the places we would like to experience: Gubbio, Perugia, Urbino(Le Marche) and Spello. We have been to Orvieto and Assisi. We prefer to travel by train and bus if feasible. What should we cut out? How long to stay in each place? We love art, history, hiking, and hope to do an Umbrian wine tour.
Thank you for your suggestions.