While I've shared each of our Italy stops in great detail, I wanted to do an overall post with our full itinerary along with few additional notes and tips that you might find helpful.
Our trip was 16 days long and we visited a total of 7 cities. While it was hard to narrow down the stops (I'm pretty sure there isn't a town I don't want to see in Italy!), there were a few things we took in to account. First, was the starting and ending points (for us, that was Milan). From there, we printed off a map and circled all the places that were high on our list to visit. We then checked on things like weather (it was high rainy season in Venice making it an easy choice to cut from our itinerary) and whether there were different activities that we either wanted to see or that could effect things like crowds and prices of lodging (i.e. October is the truffle festival in Alba). After noting these things and making immediate cuts or moving places up on the priority list, when then use different color pencils to draw/connect the cities in a way that made the most sense. We played around with various combinations, giving bigger cities more days (although we learned some didn't get quite enough), before settling on our final itinerary. From there our last to-do was booking our Airbnb's and train tickets. Of course, there can be a few mishaps, like accidentally booking the same set of tickets twice and then having to reverse cities (i.e. we had planned to go from La Spezia to Rome then up to Florence and then Bologna instead of going up and down, but someone, I won't say who, accidentally booked our tickets incorrectly!), so while it is good to have an itinerary when you're going so many places, it's also good to be flexible. Below is our full Italy itinerary-
Day 1- Leave NYC, fly into Milan
Day 2- Arrive in Milan (via Rome in the afternoon, local time)
Day 3- Milan
Day 4- Take the train from Milan to Lake Como
Day 5- Lake Como
Day 6- Travel by train from Lake Como to Torino (change trains in Milan)
Day 7- Torino
Day 8- From Torino to La Spezia by train
Day 9-Head to Florence by train after spending the night in La Spezia
Day 11- Leave Florence by train to go to Bologna
Day 13- Travel from Bologna to Rome via train
Day 15-Leave Rome and take the train back to Milan
Day 16-After spending the night in Milan, fly back to NYC
A few last tips
*While you could definitely rent a car to travel from city to city, we chose the train for a couple of reasons. One it was cheaper, two we didn't have to worry about parking (which we heard could be a nightmare/expensive) and lastly, it was a more scenic ride that we both got to sit back and enjoy together. A few things to note- we booked our tickets prior to leaving online, but there are kiosks at the train stations where you can purchase tickets (just as a heads up, be especially careful of pick pocketers around these kiosks and, if you have a travel partner, I suggest one of you faces out while the other is buying the tickets). Also, do note that some of the trains will have assigned seating, some will not, but they all have plenty of luggage racks and room in each car.
*Do keep in mind that certain cities have a tourist tax. For our itinerary, those cities included La Spazia, Florence and Rome. If you are staying in an Airbnb you will need to have cash on hand to give to your host who will then take care of paying the tax for you. And don't worry about researching which cities have the tax and how much it is...each host will tell you beforehand.
*The restaurants in Italy all have a service tax. This is meant to cover the service, although it may be worded as covering the bread and water. It generally ranges from 1 to 3 euros, depending on the restaurant, and it can be found at the bottom of the menu. Since this is considered the service tax, you aren't required to tip additionally, but you can if you choose to. For example, we would tip a couple euros extra when the waiters would really take the time to explain different dishes to us, or help us order in Italian. Unfortunately, in some of the cities with higher amounts of tourists (i.e. Rome, Florence, Venice) additional tips are now expected even though the restaurant is still charging you the service fee. You can read more about tipping in Italy here and here.