Sicily and/or Puglia , Italy

I went to both Sicily and Puglia in 2015 as part of a summer-long trip. The time of year you are planning is much smarter!

How much time do you have? Sicily is large and sight-rich. With a car I recommend a minimum of 2 weeks for Sicily alone. Even with two weeks and a car, painful cuts will need to be made. If traveling by public transportation, some extra time is really needed. It's manageable to see Sicily by train and bus, but it takes longer to get around.

Puglia is also interesting, but I think you can get a decent idea of that region in a bit less time than Sicily requires, so if you are trying to keep the trip to just a week or ten days, I'd suggest focusing on Puglia. You can include Matera in Basilicata as well. My base in Puglia was Lecce, a lovely Baroque city that--at the time of my 2015 visit--was the origin for some van trips to smaller towns in the area, arranged by the tourist office. The trips were basically transportation-only, usually with a non-English-speaking driver. That worked for me, because it allowed me to see more than one small town per day; I probably wouldn't have been able to pull that off via public bus or the occasional train. I'm sure there are also some more traditional (and more expensive) bus tours available.

One issue you'll run into is that transportation between Sicily and Puglia makes for a long day. I tried to get cute, taking a bus rather than a train because the bus was faster. Unfortunately, it didn't work out that way. The bus showed up at least 2 hours late because of problems with its air conditioning (stuff happens). They tried to fix it (thus the delay) but could not, and no replacement bus could be found, so we had a day-long trip across southern Italy via non-air-conditioned bus in July.

I didn't research flights from Palermo or Catania to Bari or Brindisi; something like that might have been an option, but I really don't like spending time in airports in the middle of a trip.

The problem is......both are wonderful. There is so much to see in both.

You don't say how much time you have.

We went to Puglia for ten days, then on to Sicily for a longer amount of time,
2 1/2-3 weeks. We took a flight from Bari to Palermo, 50 minutes, on Volotea., very easy and inexpensive.
This itinerary worked well for us. If you are only able to visit one, choose Sicily. But we really enjoyed Puglia too and the Volotea flight makes it very easy to combine them. They also had flights from Bari to Catania. Volotea reminded us of Southwest. We went in October and the weather was perfect.

I'm presuming you mean September or October 2022?

This is always going to be a matter ourely of opinion. I've done both and far prefer Sicily. I'd go as far as saying that of all the regions of Italy that I've visited, Puglia is probably my least favourite. That's not to say it was unenjoyable - when I read my own travel diary from the time, I obviously had a good time, but it just lacked something for me - I'm probably just not a lover of Baroque churches,

Sicily, on the other hand, is one of my favourites - I've been twice, both times for two weeks - and that is nowhere near enough. I think that for me, it is the vast amount of history in Sicily - Greek, Roman, Norman, Arabs - so much to see, so many interesting sites from the Temples at Selinunte, Segesta and Agrigento, the theatres at Siracusa and Taormina, the superb mosaics at Villa Romana del Casale (the best I've seen anywhere - I prefer them to those at Ravenna which are also brilliant). On top of that you can take a ferry across to the Aolian Islands.

Would I try and do both at the same time? Probably not unless I had at least a month.

haven't been to puglia so i can only talk about sicily. was there for 28 days in june and july this year. traveled entirely by public transportation. i loved every moment even if it was humid and hotter than hades! depending on how many days you have, you should set up base camp in some of the big cities. I spent 7 nights in palermo, 3 in trapani, 6 in siracusa and 2 each in enna, catania and messina. here are my thoughts:
-palermo: i am particularly fascinated by norman architecture and palermo and its surrounding has some of the finest examples. san cataldo, cappella palatina, la cuba and castello ziza to name just four in the city. Then there is monreale and the duomo in cefafu. both must see in my opinion! certainly agrigento is easier to get to from palermo by bus, train or car. not to be missed-street food at the ballaro market!
-trapani: personally i didn't find trapani particularly interesting. good base for visiting segesta and erice though. segesta is less extensive than agrigento but the landscape is more picturesque. erice is a must-see with its serpentine cobblestoned streets. instantly takes you back hundreds of years. a day trip to mazara del vallo was a wonderful surprise especially the district called the kasbah with its whimsical tile decorations.
-syracusa: ortigia is lovely with plenty to see. siracusa proper is less interesting but the ears of dionysius cave and caravaggio's 'the burial of saint lucy' (if you are into art) are worth seeing. siracusa makes a great base for visiting the sicilian baroque towns. noto is my favorite but ragusa, scicli and modica are all beautiful, especially if you enjoy not just baroque, but sicilian baroque!
-aolian islands: i strongly suggest stromboli. the narrow streets, the sparkling white asymmetrical houses with colorful doors and windows, and of course the active volcano! stay overnight if you can. eat at punta lena and order the pasta alla strombolana. you won't be disappointed!
-catania: great base for etna. acireale and randazzo are wonderful day trip destinations. especially randazzo with its unique black lave stone churches. did a day trip to caltagirone. while the ceramics are amazing, the town itself not so much. the famous steps look better on camera. my opinion is based on only a few hours in the 'centro'.
-enna: lovely hilltop town. did a day trip to piazza armanina mainly to visit villa romana del casale. the mosaics are breathtaking. the city center is gorgeous too.
messina: port city. i stayed near the duomo. the museo regionale has 2 caravaggio's in their collection. did a day trip to vulcano via milazzo. it is worth a day trip if you climb to the rim of the crater.
I bypassed taormina and missed salinunte, polizzi generosa and many others. i could go on and on. i love art, architecture and history so sicily was a dream destination for me. what i didn't expect was the experience of meeting the people of the island. i have to say they are some of the warmest and kindest i have met on my travels. they went out of the way to point me in the right direction when i could barely articulate my question. from my airbnb hosts in enna who insisted i have lunch with them every day to the teenagers in acireale who walked me to the bus stop, sicilians disproved over and over again every stereotype they are subjected to. anyway, hope this helps a little. enjoy planning your trip!