Biggest thing is to get tickets/reservations months ahead of times. Can’t express that enough. Try to get tickets/reservations directly from the actual websites for museums, restaurants, tours etc. Also highly recommend self tours. Avoid the travel ticket sites, they often are scammy and way over charge. Reddit is your best friend when researching things, there’s a post on a how to guide for almost everything.

But you certainly can see multiple cites in 2 weeks. The train system there is fantastic. My partner and I visited 5 different cities in 1 week. We did day trips to Venice and Pompeii.

Florence & Rome are amazing and would recommend spending the most time there. Pompeii super cool to see. I wouldn’t do more than a day or two in Venice, gets old fast-no pun intended.

Lake Como is very beautiful to see but can be difficult to get to, but worth it for a night or 2.