Sicily in October for about 9 days

I suggest you reach out to the vloggers Leave Everywhere and Wander who now live there. They're dealing with a health crisis but might appreciate the opportunity to do something a bit different.

We did 9 nights last April without a car, 3 in Taormina, 3 in Siracusa ( Ortigia) and 3 in Palermo. Train and bus between them. It was nice to have two full days in each. You won't need ( or probably even want ) the car in Palermo. I would give at least 3 nights to Palermo to get over jet leg, as well as it has the most sites of the 3 places we saw.
It is a big island, and if you haven't booked your plane flights yet, you could also consider just doing one side ( east or west).

You could take a look at the Rick Steves tour itinerary ( 10 nights) and drop one of the places he goes. I always thinks he covers ground a bit faster than I would like but it would give you a rough guide to start
https://www.ricksteves.com/tours/italy/sicily-2025

You can do quite a lot by car in nine days: perhaps Palermo to Agrigento, to Ragusa, to Ortigia, to Catania. If you are interested in Villa Romana del Casale, stopping there would add about an hour of driving time between Agrigento to Ragusa. Visiting the Valley of the Temples at dusk was a highlight for us and there are some nice beaches nearby if the weather is still warm. Modica, near Ragusa, is a lovely stop. We drove around Mt. Etna from Taormina but it is likely possible to do from Catania as well. Have a wonderful trip!

The big Sicily essentials imo are 3 nights in Palermo and 3 nights in Siracusa (Ortigia) and then add on from there. I think a night in or around Agrigento is next up to see Valley of the Temples. Agrigento connects with Siracusa via the autostrada quite well, and Villa Romana can be seen on the way. (If you’re into history, these two sights are essential.) You can add a night around Piazza Armerina to make this a little easier, and there are a couple other lesser sites nearby (look up Morgantina.) I have to note these smaller towns can be real sleepy, so it’s probably more about logistics than travel experiences.

Ortigia is an easy place to enjoy, and if you add a day or two here it makes a pretty easy base to hit a couple of the hill towns by car. And it’s close to Catania. You could even ditch the car at some point there and get to the airport via bus.

Hi Janet - I was just in Sicily for 9 nights in April with a friend. We spent 3 nights in Palermo, 3 nights in Ragusa, and 3 nights in Ortigia. We rented the car at the Palermo airport and headed east towards Cefalu but before reaching it, headed south on more rural roads thru the Madonie Mountains. Passed by and thru small rural mountain villages and saw gorgeous landscapes. We loved the drive along the fairly empty roads. We stopped in Petralia Soprana for lunch before heading to Ragusa. In Ragusa, we spent our first overcast on/off rainy day relaxing and exploring Ragusa Ibla and the next full day roughly following RS driving loop of the SE Baroque towns. Best cannoli in Scicli (small shop is called Cannolia). This middle section of the trip did not feel crowded or touristy at all. We then followed the coastal roads on our way to Siracusa and had an impromptu noon time bathroom stop along the way at Soda Thanks, a beachside restaurant in S. Maria del Focallo and ended up staying for more than an hour sipping our spritzes on the beach and walking along the empty fine sand beach. Just gorgeous. We then had lunch in a Marzememi (used to be a fishing village) before heading to Siracusa where we dropped off our Avis car before heading to our Air BnB in Ortigia.

Last year in October we flew into Catania and left from Palermo so we were traveling in the opposite direction from your trip. The ancient theatre in Taormina was stunning. Also, we really enjoyed staying at IblaRooms hotel in Ragusa driving en route to Agrigento from Siracusa. But be prepared for some steep hills in Ragusa. We stayed in Ragusa only one night which was enough, but it's such a picturesque laid-back town that I wish we had more time to stay another night. Valley of Temples was a highlight as was Segesta. Try to make time for spectacular Segesta if you enjoy archeology.