Lake Como / Lugano - Lugano is nice, I've had short stays there on several occasions. I don't know if you already spend much time in the Swiss Alps but between Lugano and Ponte Tresa is a summit with a nice view:
Monte Lema. I've made three 16 hour hikes to Monte Lema with my scouting group, there is a route on the ridge. For tourists there is a possibility to go there with the post bus and the cableway. Winter break starts November 13. (It may be windy on the summit but it's less cold than in the northern Alps because it is only 1624 meters above sea level). There are some other cable lifts in the region, too (
Link). (
View from Monte Lema to the hiking trail, cableway, Lago di Lugano and the summit restaurant).
Other cities in Ticino that may be worth a visit are Bellinzona and Locarno. From Lugano you can also reach the border location Ponte Tresa
by train.
Cinque Terra Never been there but it looks like it's worth a visit!
Florence / Pisa Florence is a good choice. Pisa is smaller than you may think. I was there for three nights and I didn't really know what to do after we've been at the tower. We didn't prepare ourselves carefully, though.
Rome Good preparation is recommended because there is soooo much stuff to look at! I liked it there but beware of pickpockets and street hawkers.
Posotino / Rivello It looks pictorial but a bit boring, too... Why did Posotino find your attention? Do you like hiking or do you plan to visit relatives here?
/And where else do you go in Switzerland if I may ask?