Italy has been especially crowded these past few years. All the places on your itinerary, except for Modena, will be packed with tourists. Accommodations will be very difficult to find at this late date. Please note that the villages of the Cinque Terre and Amalfi Coast are not very large and will have limited accommodations. I would recommend that you make reservations ASAP. I’ve traveled to Italy 15 times and I am pretty familiar with the places you have on your itinerary. Some suggestions: 1. Milan is a huge city - it has a more Northern European vibe - with many important sites. Research what you want to see/visit ahead of time as two days really aren’t enough. And if you want to see the Last Supper by da Vinci you need to get tickets ahead of time or sign up for a tour as there is a strict limit on numbers of visitors (and for only 15 minutes )2. How are you traveling between places? Renting a car or public transportation (trains,buses)? You have to factor in travel time between cities. You basically lose around a half day when you change cities. Be aware that Cinque Terre will be difficult to reach from Modena without a car. Cinque Terre will also be super crowded and you cannot drive between the five towns- there is only a local train. 3. In Florence it is essential to get tickets for the Uffizi and l’Accademia (Michelangelo’s David) ahead of time (purchase online). 4. Naples alone requires at least three days to explore. Take a food tour to experience the amazing street food.Procida and Ischia each are day trips by ferry. Both are quite lovely and, in my opinion, magnitudes better than Capri. 5. Amalfi Coast will be incredibly crowded and very expensive, especially Positano and Capri. Honestly there isn’t much in Positano except for the views - the beach is pebbles, restaurants and hotels are overpriced, and it is a major tourist trap. It’s where you’ll find Instagram influencers and lemon-themed souvenirs made in China. Amalfi and the other coastal towns as well as Capri will be overrun by tourists, too. Accommodations will be hard to find. Capri requires only one day as a day trip from Positano or Sorrento. If you really want to see the Amalfi Coast, I would recommend staying in Salerno, located at the southern end. It is a wonderful small city that is nowhere as expensive as Positano or Sorrento and has daily ferry service to all the Amalfi Coast towns and to Capri. It is on the high speed train line from Rome and Naples, making travel pretty simple. 6. Three nights is not enough to even scratch the surface in Rome. I would recommend staying at least four nights. Also it is essential to purchase tickets in advance to the major tourist attractions (Coliseum, Vatican). If there is a specific restaurant at which you want to dine, you should consider reserving a table. 7. Be aware that you will be traveling in peak season- it will be crowded and expensive. To really experience Italy, one should veer off the beaten track for at least part of any trip. Even in the big cities, there are many hidden gems if one is willing to explore down side streets and alleys and venture to reside neighborhoods. Buon viaggio!