Sicility itinerary

I suggest more than five nights, lol! I can't imagine narrowing it down to five days--have you chosen where you will arrive/depart yet?

Yes, more than 5 nights!

For only 5 nights I would suggest flying into Catania. Spend 4 nights in Ortigia, possibly using one day for a day trip to Noto and Modica. Spend your last afternoon and night in Catania before flying out.

I drove but we were a group going many other places. You don't need a car in Ortigia or Catania.

Are you flying in and out of Sicily? It's about a one hour flight to/from Rome to Palermo or to Catania. I suggest that you pick one side of the island and stay in one place for five nights using that as a base for day trips. From Palermo (a fabulous city), you can day trip by public transportation to Agrigento (Greek temples, 2 hours by train), Monreale (magnificent cathedral, 40" by bus), Cefalu (seaside town; one hour by train), and Segesta (Greek temple and theater; one hour by bus). If you choose the other side of the island, you'd fly in and out of Catania, then take a bus or train one hour south from the airport to Siracusa and stay in Ortigia (the beautiful, very old, historic part of Siracusa). Use that as a base for day trips to Noto (Baroque town), Mt. Etna, and maybe Taormina. Or do a full day trip from Siracusa using a guided small tour group to the three baroque towns of Noto, Modica, and Ragusa. You don't need to rent a car for any of this. You can do the day trips on your own, or use one of the many tour companies that run day trips to these places. Viator has lots of ideas.

The problem here is that Sicily is a fairly big island. Unlike the Amalfi coast, which is a region - you can pick a base and see a lot of Amalfi coast in 5 nights. You can’t do that with Sicily as a whole.

You need either more time or to pick an area of Sicily. You also need to be within a few hours of a major airport so you aren’t spending all your time getting to some remote place. So this leaves Catania and nearby (Taormina, Etna, Siracusa) OR Palermo and nearby (Erice, Cefalu, Monreale) Pick an area and go from there. A car is nice when not in the city (Palermo or Catania, especially). Public transit is fine but takes longer there than some other places and your time is limited. But driving IN Palermo or Catania would be crazy. Get the car when leaving the city.

My two favorites were Palermo and Ortygia (island in Siracusa).

Five nights is just not enough to cover much of Sicily. Focus of one side of the island, two places tops. I would either split those nights 3-2 Taormina/Ortigia or Palermo/Cefalù. Personally, I’d lean Palermo & Cefalù. Palermo is awesome, one of my new favorite European cities. There’s plenty to see and experience, and the city consistently defied my expectations. It’s beautiful, vibrant, wild and quite cosmopolitan. Monreale is a must, and you can arrange a tour day trip to Segesta or something if you like.

Sicily is a little larger than New Jersey (don't know if that helps you). With 5 nights, you're looking at seeing some the northwestern coast, Trapani/Erice and/or Cefalu and Palermo, or the east, Catanya and Taormina and/or Syracuse, maybe a day trip to Etna. What drew me to the island were the Greek temples and the Byzantine Roman villa. If you want that, you'll need a car and only see them. The three areas are very different from each other.

I spent 2 weeks there and skipped many places because there wasn't time.

Rather than such a painfully short visit to Sicily, would you onsider Puglia? It's a very interesting area, not generally over-touristed, and you could see quite a lot there in the time you'll have available.

You are aware, I hope, that you will have to fly in and out of Sicily or take an overnight ferry, probably to Naples.

As long as your expectations are that in 5 days you can see a part of sicily, I say go, and enjoy! Pick one area, and stay there, and maybe do a day trip. I am going to Sicily in October as part of my trip, have 6 nights, and got the same advice - not enough days. Well, of course its not enough to see the whole island - was never my goal . Just with any other place, stay with your travel philosophy, research, go, have fun (I do not enjoy 5 locations in 10 nights type of travel. I prefer to go somewhere, and immerse myself). Sometimes we have a limited number of days - that's what we have :-). Just pick a place, go, enjoy, explore.

Some good suggestions - I would either go to Palermo, and stay there with day trips, or East Coast,Taormina or Siracusa with day trips.

Glenn

For context: I have made three 3-week trips to Sicily.
October 2019 will be my fourth 3-week Sicily vacation.

Never enough time. I always leave wanting MORE!
I choose an area - and breath it all in.
Read about Sicily - where does your heartbeat quicken? Visit that area this time.
Don’t run around.
Sicily isn’t a fast food country.

I'd rent a car and do day trips from Ortigia. Stay near Piazza Duomo and everything is in walking distance (or was for us at 62 yrs.) Lots of possible day trips from here. We were in Sicily for 3 wks in May, staying in Ortigia, Piazza Armerina, Agrigento, Trapani, Castellamarre del Golfo, and Palermo. We drove 2500km and walked 185mi and felt we just touched the surface. So much to see, great food, and wonderful people. Castellamarre del Golfo and the nearby sights were also great. Honestly loved it all but with 5 days I'd stay in Ortigia, flying into and out of Catania. You will just have to go back.....we are.