Need feedback on Fall 2017 itinerary

Looks very pleasant. You aren't rushing. Personally I start to feel a little monotony in the rhythm of a trip when it's cut up into many roughly equal chunks. I'd try to find a place to base out of for 6 or 7 nights in the middle of the trip where you can fully recharge, forget how many days you've been there, just live life in the place, take some interesting day trips maybe if you get bored. I very much like to have an apartment in this part of the trip, not be in a hotel. Maybe you rent an apartment in Florence for a week, shop at the local markets, rent a car here and there and take in the countryside, see the less frequented sights, day trip to Lucca ...

I like that you have Rome last. I like doing the most challenging city last in a trip because by then I'm both fully used to navigating the culture and in need of a little more stimulation.

Consolidate Orvieto and Spoleto with a stay in Todi.
http://www.mapsofworld.com/italy/regions/umbria.html

Arrive in Milan - two nights
Travel to Varrena on Lake Como - three nights
Travel to Cinque Terre - three nights
Travel to Volterra - two nights
Travel to Lucca - two nights
Travel to Florence - four nights (hopefully do a day tour of the Chianti wine region)
Travel to Todi - four nights (with day trips to Orvieto & Spoleto)
Travel to Rome - four nights

Thanks for your responses. I like the idea of staying in Florence longer and doing some day trips from there. I plan to checkout Todi, a place that I am not familiar with!

I'd like to offer a suggestion for Day trips out of Florence. . . we did 2 different tours with WALKABOUT FLORENCE and they were both wonderful . . . we did the CHIANTI WINE & FOOD SAFARI and the BEST OF TUSCANY. You can book directly on their website. We did Italy Mid Oct a couple years ago and many people on this forum told us NOT to do Cinque Terre because it was the rainy season. So we did Sorrento instead. Happy Planning.

You will love Varenna on Lake Como - we stayed there on the RS 17 Days Best of Italy tour. Also, I flew into Milan and spent 2 nights there before taking the train to Varenna, super easy, by the way. Enjoyed Milan, even though it is a busy modern city, there is a lot to see of historic and cultural interest. The Duomo, The Last Supper, I also enjoyed visiting some of the older churches and the Brera Art Gallery, La Scala Museum, did not get to an opera though.

Cinque Terre - we stayed in Monterosso, a charming seaside town. Great hiking along the hills between the villages. When we were there last Oct. it had rained quite a bit and some of the trails were muddy. I believe Oct. tends to be rainy. The temps were very pleasant and by the time we got to Rome, a little warmer of course, but still pleasant. I was there from Oct 7 - 25 for your reference for weather considerations.

Happy travels,
Judy B

Todi, a place I love, is difficult to use as a base without a car. There are buses but the schedules are challenging.

I would keep your original plan, take a night from Orvieto, add it to Firenza and visit Lucca from there (about an hour away by train or bus).

A nice daytrip from Roma would be to Frascati.