Is my 20 days itinerary for center-south Italy OK ?

Thank you for your kind and detailed reply! :) I did meant Bologna by the way. It was meant to be a stop in the way from Venice because the drive seemed long..

Based on your comments and on other inputs I have tried to revise the plan:

1. I have removed Venice - I decided to do Venice in the next time we would be in Italy (planning on a trip to the north to see all the lakes).

2. I have removed Bologna

3. I added 2 nights to Florence, and I'm wondering if I should do the first night or two at Pisa since it's closer to Bergamo and I would only arrive at evening so I could get up the next morning and do Pisa/Cinque Terre and save the time coming from Florence. On the other hand I though that staying all nights in Florence would give me flexibility dealing with rainy days

4. I switched the 5 nights from Naples to Sorrento

5. I removed Milan

Regarding transportation - I saw that the trains are quite expansive, and I wonder if renting a car isn't a better option both in terms of cost and time management.

What do you think ?

I don't think you should underestimate the importance of sorting out where you are on Christmas day. This is probably tbe quietest time of the year in Italy, many people will be at home with their families from midday on 24 December until 26 or 27 December.. Some shops, hotels and restaurants will be closed, and those that are open will be very busy with family parties and groups.

As your plan is city based with a few day trips, I would definitely avoid a car, and travel between cities by train. High speed trains between main destinations can be good value if booked well in advance. Local trains - such as Pisa to Florence for example - are cheap and with fixed prices, so no need to book these in advance.

Train will be cheaper than car,unless you are a group of people. ..and will be easier even then.

Italy is not a good place to drive in large cities and most tourist towns.....parking is difficult, roads are small, many centres are resident only.Petrol is very expensive too.

I switched the 5 nights from Naples to Sorrento

Again, if it were me, I'd base myself in the city with the most indoor attractions--in this case, Naples.

trains are quite expansive

Not if you buy in advance from the source: trenitalia.com (also check thello.com).
The cheapest tickets are usually available 90 days in advance--do a mock search for 89 days from today to see potential prices.

But note that there's a semi-annual timetable change-over in mid-December that might make it difficult to purchase tickets that far in advance for late December/January.

Also note that most discounted fares have restrictions that make them much like plane tickets. Your ticket will be valid for that train on that date at that time. This is only for the longer trips; prices for regional trains don't change so there's no point in buying those in advance.

The suggestion to base yourself in cities assumes you'll be taking the train. A car will be an outright hindrance in Florence, Rome and Naples.

Speaking of planes: are your flights already booked? If Florence is your northern-most stop now, it would make more sense to fly into Florence or Pisa.

On the other hand, if you're stuck with Bergamo, you may want to see if you can add Venice back onto the end of this itinerary to enjoy the lowest hotel rates of the year in early/mid-January.

I assume this itinerary will go through several revisions in the next 6 1/2 months. The week between Christmas Eve and Jan 2 is considered "high season" so you may want to sort out that timeframe first.

You know that it's freezing/ice cold in december/january in Venice, Milan, Cinque Terre, Florence?

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