Sorrento - I have been there 4 times in the last few years and I love it. The people are wonderful, the accessibility to places like Capri, Positano, Amalfi and Ischia is very easy, the restaurants and a wonderful old center of town for shopping and people watching. The scenery is beautiful also.

Second would be Venice - for it's uniqueness. There is nowhere else in the world like it. A must see!

Lastly is Rome for the history and the things to see. Wonderful shopping, restaurants and the piazzas are great people watching places. A trip to Italy would not be complete without seeing the things in that city. I would do Rome first because it's exhausting and then Venice and finally relax in Sorrento.

I'm so jealous!

Siena, Capri, Positano or
Venice, Florence & Rome

Venice - for the canals and small strets - wonderful photo ops!

Bologna - for its food, crooked towers, and covered passages

Montepulciano - for its hilly streets and a great apartment I rented for a week; also a great homebase for the Tuscan towns in the area.

Monica

Florence, Assisi, Como / Bellagio

Florence, for everything it offers

Taormina, for the sheer beauty of the town

Rome, for the amazing history on every corner

Positano for a vacation from your vacation.
Bellagio for the most romantic looking and friendly place imaginable.
Rome for the Ancient to the Renaissance.