Itinerary recommendations for 2+ weeks Sicily in December?

Get hold of Rick’s videos on Sicily and a good guidebook, I believe Rick now has one. I recommend the following stops: Taormina for the Roman theatre with great views of Etna. Good centre to explore Etna. Also visit the English Gardens with stunning sea views. Selenite a major Greek settlement, largely unexcavated; the Acropolis is close to the shore line and inland there are three temples in various states of disrepair. The Norman cathedral in Mont Real just outside Palermo, stunning mosaics cover the church interior. Also the Norman Cathedral in Cefalu, again covered in mosaics. Cefalu is very neat small town to explore. Erice, medieval hilltop town. Trapani, check out ancient salt pans still in use, and a Madeira winery. There are lots of other interesting places to see, the guide books will help.

@Ianlubber thank you -- yup, I watched his 2018 video last night, and it definitely was helpful. Definitely came away with feeling like the Northwest (Trapani, Erice) and Taormina were must-visit places. It's a little harder for me to decide how much time we'd want to spend in Palermo or Catania, versus using them as connection points and mostly spending time in smaller towns. The Southeast (Modica, Siracusa) also sound very compelling.

I ordered a few travel books (the usual suspects) and will keep reading those to decide.

Palermo has a lot of sights (and Monreale is easily visited while staying in Palermo). Siracusa is smaller, but the Ortygia section of the city is a favorite stop of many of us, and the Baroque towns of Modica, Noto, Ragusa and Scicli are manageable by train and/or bus from Siracusa.

A lot of us are not great fans of Taormina. It is beautiful but touristy and full of international boutiques. Perhaps it would be less so in December, but I'd do some investigating before planning a multi-night stay there. You might absolutely love it. But you might be like me and glad to leave after a few hours.

We flew into and out of Catania . The first few day we stayed nearby and visited Catania, Ortigia and Noto. Then on to Villa Romana Casale and Agrigento, Marsala, followed by Erice/Trapani, Monreale (day trip to Palermo), Cefalù, and finally Taormina. We had a rental car.

i spent about a month in june-july of 2021 in sicily. palermo is full of incredible architecture. stayed for 6 days and it was just enough to experience all that I wanted to. did day trips to cefalu (norman cathedral) and agrigento (greek ruins) from there. if you like art don't miss antonello da messina's 'virgin annunciate'. next stop was trapani. was a bit of a let down after palermo but erice (gorgeous unspoiled hill town), segesta (greek ruin surrounded by beautiful landscape), and mazara del vallo (beautiful square, norman church, and a whimsical area called the kasbah) more than made up for it. enna in the middle of the island was next - day trip to piazza armarina (beautiful baroque town) and the nearby villa romana del casale (amazing mosaics). stayed in siracusa for 5 days just across from ortiga island (lots of great architecture, a caravaggio, and the 'ear of dionysius' cave). made day trips to ragusa, noto, modica and scicli. each a beautiful example of sicilian baroque architecture. next, catania and day trips to caltagirone (famous for ceramics otherwise not impressive to me), acireale (great cathedral) and randazzo (really cool lava stone architecture. the journey itself was fascinating-on the narrow gauge circumetnea rail line). final base in messina (lovely cathedral, norman churches and two important caravaggios in the local museum). i did all of this using public transportation except for having to take a taxi to go from piazza armarina to the villa romana del casale. i am sure you won't have the crowds of summer but on the other hand, check the opening hours of each site you visit and the bus/train schedules for winter. if you like take a look at the link in my profile for some pictures of my trip. you'll love sicily! good luck.

Our first trip to Sicily will be the RS 11 day tour starting Dec 4th - so I can't make specific recommendations at this time. An idea might be to use an RS itinerary as a model and vary it to suit your needs. Our experience with RS tours is that they have a good balance of free & organized time, stays in each city that are just long enough to see local attractions and a fair but not excessive amount of walking.

I've been using this forum to find recommendations on additional things to see during the free-time periods. We have a couple of extra days in Palermo at the start of the tour as well and want to identify options for this. Special thanks to previous poster 'alomaker' (followed the link to his 2021 Italy photos and many were in Palermo). I now have more ideas and wish my photography skills were this good. I plan to get up really early in the mornings and take my camera for a jog. I did this in Rome and got lots of shots before the traffic and crowds.

From what I've read, you should be able to get by without the hassle of renting a car. Public transport appears to be good.

Also, it looks like there will be no shortage of ancient ruins and architecture wherever you go. The Greek ruins are our main focus as a precursor to a RS Greece tour we have booked for next Sept. After reading all the info on Sicily though, I think this may just wet our appetite and that we'll have to schedule another Sicily trip somewhere in our bucket list.

We were told multiple times while on the RS tour, Sicily has more well-preserved Greek ruins than Greece. I think it would help to read the RS Sicily guidebook to help narrow down places worth seeing. But I'm going to guess it would take up a lot of time to get to any of the places we saw by public transportation. I would not drive in Palermo, but outside of that, it looks pretty normal by US standards.