Sicily in late January

What's your interest? Greek/Roman history? Food? Check the historic weather Sicily weather averages and note that it wont be warm and sunny if you're thinking beach time. Yeah, we're all concerned about COVID. Any extra risk you're thinking with Sicily versus anywhere else in the world, including NYC?

Given the short amount of time (at least 2 weeks would be needed to visit the whole island) you are doing the right thing to concentrate in one area. January in Sicily, at least on the coast, is mild compared to NY. Temperatures should be in the 50s F, even low 60s during the day, but with high chance of rain (that is the wet part of the year in Sicily), so basically SF Bay Area weather. Therefore I would stay in a big city which offers plenty of opportunities for activities indoor (museums, etc.). In my opinion Palermo is the best choice in that respect. Beautiful city, with also several day trip opportunities (Cefalù, Segesta, Erice, etc.).
The area more or less along Via Maqueda, between the Politeama theater and the Piazza Quattro Canti is in my opinion the best to look for a hotel. It’s the nicest more upscale area of the city center.
Nobody knows how Covid will be in January. Sicily is not the hardest hit region in Italy (the north is) and given the fact the weather allows more outdoor activities it’s easier to follow social distancing norms.

Some good source for research on Sicily:
http://www.bestofsicily.com/

I discourage short trips to Sicily because there's so much to see there, but perhaps you figure you'll be in serious need of a break at that point (and I'm afraid you're right) and are trying to maximize the possibility of sunshine. The thing about Sicily, though, is that it's going to add an extra flight leg coming and going, which could be annoying on a short trip. In any case, be aware that Sicily has two airports you might be able to use. Catania actually has more flights than the capital, Palermo, but you should have multiple connection options in Europe to get to either one. If you didn't want to spend all your nights in the same place, it would be possible to book a multi-city flight into one of the Sicilian airports and out of the other one.

My choice of destination for a one-week Sicilian vacation with the possibility of side-trips would be either Palermo or Siracusa. Palermo is a big, hectic, sight-rich city. It has picturesque markets, an excellent archaeological museum, and many striking churches and chapels. The obvious side-trips are to the coastal town of Cefalu (by train) and the magnificent, mosaic-filled cathedral in nearby Monreale (by bus). Cefalu's a popular summer spot; I don't know who lively it would be in winter, but it's very handsome. Another possibility would heading into the interior to see the Villa Romana del Casale outside Piazza Armerina, which might require a taxi from Piazza Armerina in the winter; I believe there's occasional bus service in the summer. There's probably also some form of transportation that would get you to one of the Greek-temple sites (Agrigento, Selinunte or Segesta) if you're into that sort of thing.

The medieval district of Siracusa, Ortygia, is very atmospheric and is the place to stay in that area. The city has an archaeological museum and an archaeological park with a Greek temple. Major side trips are the Baroque towns in the interior, including Noto and Ragusa (the larger). Modica and Scicli are also worthwhile. Some of those can be reached by train; others require a bus trip. There's rail service up to Catania and Taormina, as well.

If I'm right that you're thinking partly about sunshine, you might also consider Andalucia. A week would be a good amount of time for Seville and Cordoba or Seville and Granada. Cordoba and Granada would also work but I don't think there's a lot of air service into Granada. As with Sicily, I suspect Andalucia would mean a connecting flight unless you opted to fly into Madrid and take the train to Cordoba as your first stop.

I have no words of wisdom on our COVID prospects in January. I haven't been to Europe since 2019 and am unwilling to commit to a ticket at this point.

Thanks so much! We don't care too much about beach, more about food and sites. Liking Butera28 and Duchess Nicoletta cooking class if she still does this. Perhaps hire driver to take us around to other cities/sites if needed.

i was in sicily in late june through july therefore can't give you advice on weather and how that affects transportation, site hours etc. my suggestion, if you you want to stay in one 'base camp' for a week, is to choose between palermo or siracusa. in palermo you have the cappella palatina, san cataldo, san giovanni degli ermiti, palazzo della cuba, castello della ziza, basilica la magione (these are my favorites) and many more baroque and norman sites. monreale and cefalu are within easy reach and amazing. to me the balaro and other street markets are not particularly interesting but the food there is not to be missed. segesta and agrigento are also easy day trips away from palermo. siracusa on the other hand, is a good base, for day trips to ragusa, modica, scicli and noto. of course, ortigia island is a part of siracusa just a few hundred feet across two bridges. lastly, regarding covid, italy is currently open to visitors but infections are on the rise. best advice would be to monitor reliable italian and eu government and news site for developments. cdc guidelines for return to the usa is also to be monitored.