First Trip to Italy

If I had 13 nights, no matter where it is, I wouldn't want to stay in 8 different places. So yes, if you are committed to seeing Spoleto, Assisi, and Cortona, I would stay three nights in one place and do them as day trips.

I would save CT for the end of your trip, because after seeing a lot of culture and history, you'll really appreciate the opportunity to just chill for a few days at the end of your vacation.

Enjoy!

Reverse the trip:
Arrive Milan MXP (probably morning)
Go straight to Lake Como by train on the same day (Varenna or Bellagio is up to you). About 2.5/3 hr trip.
Stay at lake Como for 2 nights.
Train from Lake Como to Monterosso (via Milan/Genoa). About 4 to 5 hours.
Stay in Monterosso for 2 nights
Train Monterosso to Florence (2.5/3 hours)
Stay in Florence for 2 nights.
Rent a car in Florence, drive to Assisi (about 2 hours). Spend 3 nights in Assisi. Visit Spoleto on a day trip from Assisi. You can visit Cortona on the way from Florence to Assisi (it's along the way).
After Assisi drive to Orvieto. Visit Orvieto for half day.
At this point you could return the rental car in Orvieto (however Hertz is the only company with an office in town) and proceed to Rome by train (70 min from Orvieto).
Or you could drive the rest of the way to Rome and return the car in Rome (the Tiburtina train station is easy to drive to along with a few more locations.
Spend your last 3 nights in Rome. Fly home from Rome.

I've left your nights unchanged. I saved you some hotel changes and by reversing the trip I saved you one night wasted at the Malpensa, which is in the middle of nowhere. However I personally think you are trying to cram too many locations in the time you are in Italy. You should add one night to Florence and probably one to the Lake Como. You

Kathy,

Although it may be feasible, I agree with others that you're trying to fit too much into a limited time frame. The Itinerary provided by Roberto is perfect, and that's also what I'd suggest.

For driving in Italy, note that each driver will require the compulsory International Driver's Permit. You will of course also have to specify each driver at the time of renting the car. You'll also need to be extremely vigilant to avoid the dreaded ZTL (limited traffic) areas, as hefty fines will result for any infractions.

There are also some potentially expensive "caveats" to be aware of when using trains and other public transit. If you need more information on those, post another note.

Roberto's itinerary sounds great! If you only stay only one night per place, you waste a lot of time just traveling to get there and not enjoying the town.

Thanks to everyone for your comments!

Roberto has it exactly right. PIck a town and stay there. You can easily do a bunch of Umbria and Tuscany from any of these towns, Orvieto, Spoleto Assisi, Cortona, Perugia, Todi, Terni, Deruta, Siena, and even the Tuscan wine towns. Make it easy on yourself and minimize packing up to move for one night.

I have seen the sights of Spoleto, Assis, and Cortona in one day. Don't be afraid to rent a car and get out in the country. You will be surprised at the proximity of Italian towns to one another. Easy peazy! And driving in the Italian countryside is fun.