2 weeks in Italy

What do you need help with?

What time of year, who's in your travel party, what are your interests?
For two weeks, I'd suggest you limit your itinerary to three destinations.
Have fun planning!

What time of year will this happen? It is a lot. Plot your proposed itinerary on paper. Include both your starting and departing airports, and travel times from one place to the next. How much time does that leave you in each place, compared to the time you need to see and do what you want in each place? My bet is that you will need to either extend your vacation time or eliminate a couple of places.

You might start by looking at Rick's tips on itinerary planning:

https://www.ricksteves.com/travel-tips/trip-planning

If you can fly in and out of Venice and Naples that would be ideal. If you fly out of Venice, make sure it’s a late morning flight so you don’t have to pay for an expensive water taxi to the airport.
If you arrive in Venice early morning you need two nights. Otherwise, make it three nights. If you depart from Venice, you need three nights to experience it.
Lake Como needs a minimum of three nights. I recommend Varenna which is the most scenic part of Lake Como. While there you want to visit Belagio and also take a day trip to Milan which is worthwhile. Allow three nights minimum for Lake Como.
The Cinque Terre deserves two full nights but if you hike add a night per trek. If you visit Vatican City in Rome, make it four nights. If not, then three nights should be enough in Rome.
Sorrento is a great jumping off point to visit the Amalfi Coast. You can also take a ferry between Sorrento and Procida. You’ll need a minimum of four nights for this region too.

2 weeks in Italy

Does that mean 14 nights there?

Composition (demographics) of the travelers?

Time of year?

hey hey noners
your question is very vague and no replies from you with questions asked here."alot of travel i think but...." yes it is. have you been to italy before?
many posts lately ask the same thing without any info or response. may be rude, you come to the forum, many here willing to offer you ideas and nothing. when, how many in party (adults & kids with ages)
are your 14 days on the ground, or minus 2 days for arrive/departure days which is 12 days, planning 6 towns/cities within that time is toooo much considering train travel and hotel check-ins 3-4pm/departures 10-11am, are you doing multi-city (arrive one city depart another or round trip from where with backtracking ugghh). 2 nights is only 1 day to explore
agree with CJean, work on an itinerary, how long in town, train travel time. extend dates or cut back on places. good luck planning
aloha