Cinque Terre

Just south of Genoa, the Cinque Terre is a collection of town that is is a must see on any tour of Italy.

Rick Steves shows the Cinque Terre and the enjoyable walks from one town to another. See his video here.

Vernazza — of the towns of the Cinque Terre

Naples

From Rick Steves, visit Naples then visit Pompeii. Return to Naples to visit the museum of Naples to see the extensive collection of works of art recovered from Pompeii.

While in Naples take a walk up Vesuvius. There are regular tour buses from Naples to Vesuvius.

And one must try the authentic Neapolitan pizza!

Nearby Sorrento has the great classical hotel - Grand Hotel Excelsior Vittoria.

Togs

Milan is the fashion centre of Italy and, arguably, of Europe. A good place to buy a new suit. Among the best tailors of Italy are Brioni, Canali, and Ravazzolo.

Start planning

I've started a blog for planning my trip to Italy. I want to see Florence, Rome, Venice, the Amalfi coast, the Cinque Terre, Capri, and Pompeii and Herculaneum. 
I am interested in the great art works to be found in Florence and the art and architecture of Rome.

For museums to visit in Italy see the museum "must see" list on my Art page.

Rick Steve's has lots of videos on travel in Italy:
Rome: Eternally Engaging

I discovered that there are lots of guides available through a website I've just discovered called "Tours by Locals". It has information on private guides all over the world, not just Italy, including reviews by users.

Rail map within Italy and beyond: