Fall 2015 in Sicily 6 travelers for a week

I was in Sicily in April and May 2014. My VERY detailed trip report is here: https://community.ricksteves.com/travel-forum/trip-reports/sicily-palermo-caltanisetta-siracusa-taormina

Some additional thoughts:

The easiest way to get to Sicily is flying from the Italian mainland. If you don't want to see other parts of Italy on this trip, the easiest connections from the US are through Rome, Frankfurt or Munich. Our frequent poster Roberto has explained that going from the US to Sicily through London, Paris, or Milan means changing airports, and so is not the way to go.

From Rome, there are many flights a day to both major Sicilian airports. From other Italian cities, there are a few flights a day. Look at Skyscanner to get an idea (just put in a date a few months away; this will give you enough of an idea to make plans). Note that Catania is actually a larger airport than Palermo, with more flights. I flew into Palermo and out of Catania, and doing this (or the reverse) avoids backtracking. There are also airports at Trapani (on the west coast) and Comiso-Ragusa (in the southeast), if these work better for your itinerary.

If you will have checked luggage, Alitalia allows one free checked bag on their domestic Italian flights, so they can be cheaper than a "budget airline" when all fees are added. If you want to book Alitalia, I found that their "International" website offered lower prices and more fare options than their US website. And looking at a random date in the fall (October 13), they are already showing flights from Rome to Palermo. The cheapest tickets disappear, so book as soon as you know your plans.

To accommodate 6 adults and their luggage, you will need a VERY large vehicle; you will do much better with two or three smaller vehicles, which has the added advantage of allowing you split up when you wish.

If you want to stay at the Agriturismo Sillitti, which sounds perfect for your interests, book early to get enough room for all of you. If you don't want to read my entire trip report right now, my review of Sillitti is here: https://community.ricksteves.com/travel-forum/italy-reviews/sicily-caltanisetta-central-sicily-agrigurismo

I'm not clear on your itinerary. Are you planning to spend time on the mainland before and after Sicily? I flew directly to Palermo on Alitalia (connecting in Rome) then on Meridiana from Catania to Bologna for more Italy before flying home from Rome. Since my ticket was TLV-PMO, [1] my checked bag was routed through to PMO and I knew that if I missed my FCO connection, Alitalia would put me on another flight (there were 2-3 more that day). It was cheaper to ticket the flights that way than any other option. The difference between Alitalia to Rome and to Palermo was minimal.

Harold is so right about not taking a huge car. In addition to the points he makes, you are going to be driving through towns with narrow streets, sharp turns, and limited parking. The bigger the car, the harder that will be.

Sicily is pretty big and a week is not nearly long enough, so you'll have to narrow down which towns/sights are your priorities. My favorite town on the eastern side was Cefalu, on the western side Ortigia (Syracuse), but I did not go to Taormina. Most of the towns are charming, it's not at all hard to find good restaurants everywhere, the fruits and vegetables are amazingly good, mostly grown locally, and the people were warm, friendly and patient (hardly anyone spoke English). The beaches are calendar photo-perfect. In spring, the water was too cold, but in September it should be perfect for swimming.

I bought a ticket from Catania to Genova over a month ago, not sure why you say it's too early to buy tickets.

Since you are already traveling independently, I would rent two cars, for ease of maneuverability and freedom of choice for traveling.

Five days is not a long time for Sicily. I would base either either in/near Palermo, Taormina, or Siracusa and daytrip by car to places in that area. Roads are good.

The difficult flights to coordinate so far are getting back from a trip to Athens ( between arriving in Italy in late Sept. ) and getting to Palermo in mid October- all in same day- with some time constraints . Looking at Alitalia of course....Anyone have positive/negative expereinces with Aegean/Vueling/Iberia/ Rynair? Easy jet? I think it may have been Easyjet that indiactes their timetable for Rome to Palermo only goes out to mid April. Not sure if that means they have not relased new timetables/fares for then or if they only fly certain times of year?....Appreciate all the suggestions made so far!

I've taken Alitalia from the mainland to Sicily several times, no complaints about domestic service. Transatlantic has been another story.

I have used both Vueling and have used Ryanair numerous times. These are low cost airlines with high cost baggage fees. If you travel with lots of luggage I would not use the low cost airlines. Don't think Southwest Airlines when I say low cost (not that SWA is low cost, but at least 2 free bags and comfort). If you travel with one small suitcase, such as an overhead size, you could consider one of the inter-Europe low cost carriers, but read the baggage rules, measurements, weights and fees VERY CAREFULLY!

A few years ago, we used Alitalia to get from Catania to Rome in order to be there for our return flight to SFO the next morning. Its price was slightly higher than the budget lines, but our bags were checked for free. The flight was just fine. Prices and flights Palermo/Rome were pretty much the same cost and frequency. Given your short amount of time - - did I read 5 or 6 days? - - I would base in or near Palermo. Lots to see and do there. Plenty of accommodations and restaurants. Besides the sights of the city, itself, you could go to Monreale - - the cathedral there is an absolute must-see - -, Cefalu, Erice, Segesta, oops, you're out of time. Buon viaggio.

If your desire is really to meet and connect with locals, I recommend renting an apartment through: legendofsicily.com
The booking agent, Claudio Pugliese specializes in exactly this! He not only will rent your group an apartment large enough
to accommodate all of you, but his 'hands-on' approach, walking you down the street in town, introducing you to his friends, etc., goes above and beyond any experience we've ever had renting apartments all over Europe. They have usually handed us the keys,
gave a brief tutorial on how to work the appliances, and returned in a week to collect the money from the electric meter!

We had the best two trips of our life here in Taormina, with two separate groups of friends and intend to go for a third time with different friends. He also has a tour service and will offer a guide (he has access to different sized vehicles, (or you can your own if you can fit six plus one guide in it) . Educated, interesting, perfect English. He covers the entire East side of Sicily, but his apartment rentals are all in Taormina, and there are lots to choose from. I've sent a number of people there, and they've all fallen in love not just with Sicily, but the sweet Claudio as well.