Cinque Terra, Amalfi Coast and Sicily

I think you’d need at least three weeks.

We were thinking of combining Sicily and the Amalfi Coast next year, but with only wanting to take 2 weeks off at a time we realized we'd be rushing both. Now we're leaning toward only the Amalfi Coast for the full 2 weeks. This would include Naples, Pompeii, etc. I guess it comes down to how long do you have and how rushed you want to be. For us, those 3 regions would make 3 trips.

You are considering three distinct areas that are all spread out. Do you plan on visiting just a few key spots in each area in a short amount of time or do you want to take time in each area and if so how much time can you allot? If you are still working and only have two weeks off then most likely all three places are too spread out. If you are set on seeing all three then you must be selective. If you are retired or can take time then go for it. Sicily is big and there are multiple wonderful sites to see all over the island. Sicily’s appeal and what it has to offer is quite diverse: ruins of ancient civilizations, great foods, big cities, small villages, beaches and mountains, diverse architecture, religious experiences, etc. I have been there twice and there is still so much more I want to see. I did a 22 day trip around the island and I had to prioritize and still would have liked more time. I would suggest that Sicily, if you really want to explore, be a trip by itself where you can dedicate at least two weeks or more. If you have sufficient time on this trip then you could probably do some of the Amalfi sites coupled with a few of the sites in Sicily and save Cinque Terra for another visit where you focus more on northern Italy.

Which month?
Do you just want to see the Amalfi Coast, or will you wish to see an island, Naples, Pompeii, etc.? You can hike on coastal paths there, so I would consider it a duplicate with Cinque Terre.

I did all three areas last summer, took me three weeks. You could do it in as little as two weeks I think: CT 3 nights, Amalfi 4 nights, Sicily 7 nights. It would depend on part in Sicily if you’re going to rent a car or not. You can get to some parts on trains/buses without too much trouble but a car frees you up to see more of the central and southern parts that are less accessible. If you are only doing public transportation, I would seriously consider entering/exiting in Palermo and Catania, whichever order makes most sense for you.

Would need to see an itinerary ; on the surface it sounds like a not great plan unless you don't have interests in areas in between. Are you flying from say Naples to Sicily or planning in driving?

Planning a (t)rip to Italy in the fall

"Fall" runs from the 3rd week of Sept to the 3rd week of Dec. When you plan to travel during that time would relevant info to allow folks to make useful suggestions.