Early Planning for Trip to Southern Italy & Greece

October is a great time to go to Italy, our favorite! Not too hot, not yet likely to be rainy.

Sicily alone could fill 14 to 18 nights. Perhaps getting Rick Steves guidebook for Sicily would be a good step to decide if you want to take on the entire island, just visit a corner of it for a few days, or sag eit for another trip. The Amalfi Coast stay depends on what you want to do. Will you just relax in a small town like Positano or so you want to spend time at Pompeii, for example?

We spent last October in Puglia and Sicily and the weather was perfect. Not too hot. We also have been to Greece in October, nice weather.
If you just want a little taste of Sicily, base on Ortigia Island, Siracusa’s historic district. Beautiful, great dining. Siracusa has the Greek Theater and Archeological Museum too. Near enough to visit the Baroque Noto for an easy day trip by bus or train.
Fly into and out of Catania, Sicily’s largest airport.

Here's the thing: Sicily's a large island with great sights scattered all over. I recommend at least 2 weeks there. And Greece is an entire country, plus it's one that can't be blitzed because of the lack of express-train service and the need to use planes or ferries to get to most of the islands.

Given the time you have available and your desire to include Rome and the Amalfi Coast, I wouldn't want to add on either Sicily or Greece. If I had to choose one of the two, I'd pick Sicily for logistical reasons.

I suggest looking at Puglia, though. It has a variety of sights and I think you can see a lot of the area in the time you'll have available.

I can't comment on October weather in any of those places (I prefer the longer days in the spring), but you can investigate actual, day-by-day, weather stats on timeanddate.com.

Skip Greece and save it for another vacation. If 14 to 18 days i'm guessing that includes your travel days. If so, then you have 16 nights. Think in terms of nights not days. You could spend 3 nights in Rome, 4 nights on the Amalfi coast and 9 nights on Sicily. You would need to pick the east or west side of the island. But maybe something like this
Fly to Catania and go to Taormina. Spend 3 nights. Then on to Ragusa for 2/3 nights depending on your flight off the island. 3 nights in Ortigia fly from Catania to Naples then on to Sorrento or the Amalfi coast for 4 nights. Then the last 3 nights in Rome and fly home from Rome.
You need to decide which side of Sicily interest you but you can include at least 9 nights on the island. The best part, you have plenty of time to figure it out.

This sounds like a great trip and I actually did a slight variation on this trip last spring in 2018, when I was studying abroad. I did 11 days in Italy (Rome, Sorrento/Amalfi Coast, Palermo). Then a couple weeks later I did 6 days in Greece (Corfu, Athens). You could definitely just do Italy in 14-18 days. If you're closer to just 14 days I would say just do Italy. If you're on the longer end closer to 18 days I think you could do 11/12 days in Italy and then 6/7 days in Greece. However, I think there is so much to do in the regions of Italy you are looking at it would be best to stick with Italy and save Greece for a trip on its own.

I would recommend 3/4 nights in Rome, head down to the Amalfi Coast for 3 nights, then on to Sorrento for 3 nights (from there you can do Capri, pompeii, etc), use Naples as a stopover for 1 night and take a flight from Naples to Palermo. I'd recommend at least 3 night sin Palermo and then use the rest of your time to explore another area of Sicily.

I have only ever been to Palermo in Sicily, but absolutely loved it. Tons of history and SO MANY churches and each is very different. The city was an absolute surprise to me and the food was amazing. I just loved everything about it. I would highly recommend the city if you are going to Sicily.

Thanks everyone for the feedback so far. Just what I was hoping for. We’ll definitely want to do more than just Rome and Amalfi since I’ve been to both of those before, but I can really appreciate the suggestions to consider dropping Greece. We’ll take some time to discuss what we want and maybe figure out how long the trip will be. I like the idea of 5-6 nights in a corner of Greece at the end of the trip but we’ll see. Sounds like I need to do some reading on both Sicily and Greece.

Chris,
If you have your heart set on Greece skip Sicily and save that for another trip. You could fly into Rome 3 nights train to Naples and onto the Amalfi coast for 4 nights. Fly to Santorini 3 nights ferry to Mykonos 3 nights fly to Athens 3 nights then fly home from Athens. Or fly to any of the Greek islands that Interest you.