Oops -now I see your son will be the driver-sorry about not reading carefully your new post!

Need feedback on Jan.22 itinerary. Also is booking.com a good way to book lodging? If I book on my own is a credit card safe? Do owners take Pay Pal? Any other suggestions for a booking site?

Train north to ? (5 nights)
Train north to ? (5 nights)
Train north to ? (5 nights)

Is it 15 nights total>?

Seems like a lot of time in the north. From Spoleto you can day trip or move onto Assisi and Perugia - take buses to Gubbio and Todi or other Umbrian towns

Bologna is IMO vastly underrated here - a fabulous old city

Then maybe to Milan - and to the Lake District-

Lake Stresa or Lake Como

and back to Florence.

Thanks PalenQ. After son leaves I want to spend quieter time in less touristy places and just lay back and enjoy the culture and the scenery. I hope to do another trip to Italy and stay in Bologna and Milan. I have looked into Gubbio and Todi and perhaps spend a few nights there. Is there a reason I should not consider flying out of Florence?

Yes, booking.com is a very good source. I've never had a problem with my credit card with it, and I've been using it for years. As a rule, the CC is used to secure the room (no charges now -- unless you are specifically told that there will be one). You can pay however you want once you are at the hotel. (I often use a different CC to actually pay.) Make sure you pay attention to the cancellation policies.

Is there a reason I should not consider flying out of Florence?>

No if the price is right -but if wanting to go say north to Switzerland for a spell or over to the French Riviera then you'd have to go back.

But if staying in northern Italy of course Florence Airport is easy to get to.

<Also is booking.com a good way to book lodging? If I book on my own is a credit card safe?>

I've also used booking.com for years. Features I like are that you can only review if you have actually booked a stay (unlike Tripadvisor reviews), can alter bookings easily, can choose 'non refundable pay now' option or pay at set date near arrival, use of filters to define your preferences (number of bedrooms/ location/ cost etc) to help in your planning.
I use a debit card, rather than a credit card. In fact, one hotel I tried to book directly on their own site would not allow a debit card, but I was able to book on booking.com using that card.