Greece and Italy in 2 weeks - Possible?

Both Greece and Italy are wonderful but I would not try to do both in the same trip. Even sticking to Greece, you are trying to do too much.

Moving between islands by ferry is more time consuming than you think. There is a recent post that describes how long it takes to go between eastern and western Cyclades. It is not reasonable to try to do what you propose to do. It is two trips to Greece!

For example, you could easily visit Crete and Athens for your two weeks. We spent 3 nights in Athens and 11 on Crete which is a very large island.

Two weeks in the two countries is possible, but you’ll be skimming through Greece, with pretty much one one-night-stand after another, before your three nights in Naples. If you do go to both some of Greece plus Naples in a two week trip, then at least skip Crete this trip. We had three full weeks just on Crete, and you getting there, seeing some things, then moving on to Naples would be more of a time-draining chore than an enjoyable addition to the trip.

This is one thread about the time you need on an island and the travel between islands: https://community.ricksteves.com/travel-forum/greece/two-week-in-greece-in-may Three nights on an island will only give you 2 full days.

You have too many places on your proposed itinerary just for Greece! Drop Italy and focus on Greece. Then drop some of the places on your list for Greece.

So, you’ve got two weeks, but you didn’t say if that two weeks includes travel to and from Italy. You’re thinking of visiting FIVE islands. Traveling between islands takes time. Some can be flown to but, to be quite honest, it’s a lot to pack into two weeks and you’re thinking of visiting Italy as well? Drop Italy. Think of Athens as cutting a day from your itinerary because of ferry connections. So, you’re left with 12 days at most. You don’t say where you’ll be flying into.. You also don’t say what your likes or interests are. All this matter. But definitely Italy will not be feasible. You can fly from DFW into Athens and then leave from Crete. And fly from there into Athens. Or you could do the reverse. I use sky scanner to search for flights and have found it to be the best search engine for vacations.

We did this when our daughter was 12. Florence(3 nights) and Rome(4 nights) and day trip from Rome to Pompeii. Athens(3 nights), Santorini( 3 nights), and Naufplio(2 nights but I think 1 could work-one of our days was a snorkeling trip in the area, we took a tour of Mycenae and Epidaurus from Rome that ended in Naufplio) in Greece. I've never been to Barcelona and have no desire to go. Plan your trip to start on a Saturday and end on a Sunday so that you have 16 days. Fly into Rome or Florence and out of Athens.