Puglia or Sicily?

You might look into a flight from Naples to Catania and settle down in the Siracusa area. The island of Ortigia is an amazing and different place! There are historical and archaeological sites there and in Siracusa (the two are connected by a very short bridge). You can also day trip to a few of the baroque cities in the area. Food? Don't get me started - I'll be typing all day!!!! Catania itself isn't much, IMHO, and Taormina, according to friends, is beautiful but not at the top of their 'must return' list. I wouldn't rent a car. Parking isn't easy or cheap and not very secure (from bumps and scratches). If you do want to explore the rest of the island, then rent a car when you leave Ortigia and ditch it before you check into your hotel in Palermo. Agrigento can be a 'must see' if you are into Greek temples and very interesting shorelines.

Malta needs a week or more by itself. I was there a few years ago with friends for less than a week - we still had more than a week's worth of 'gotta do this' on our list. Very, very different and fascinating!

I don't care what time of the year I go to Italy - it's a place where "I like me!"

We combined them in one trip and it worked very well due to non stop flights from Bari to Palermo or Catania on Volotea, 50 minutes. Volotea flies between smaller cities in Europe and reminded us of Southwest. On time, nice staff, inexpensive. Otherwise, we would have to have flown from Bari to Rome to Palermo or Catania, many hours and higher costs.
We enjoyed both of these areas of Italy, the seafood was especially outstanding. We spent eight days in Puglia based in Polignano a Mare and two and a half weeks in Sicily, our second time there. One week was spent in beautiful Ortigia.
Our international flights were either daytime flights from JFK or BOS to London LHR, then Rome, Bari. Return flights Catania To Rome to London to JFK. We always stay overnight at LHR. Flights LHR to Puglia and from Sicily all were with Alitalia, no problems at all.
We spent two nights in Taormina which was enough and will not return there, so overtouristed. We loved the rest of Sicily.

Puglia and Sicily are two of my favorite areas of Italy. I can't wait to go back to both.

However, I would hold off on Sicily until you have more time. Expecially if you want to add Malta. Make it a separate trip and give yourself time. Keep your current plans.

May is a good time for Puglia. It's warm but comfortably so. I was there last May. I was also in Sicily on the same trip.

I agree that Sicily needs considerable time even if you don't plan to include Malta. For a combo trip I'd research flights to Malta. The ferry was quite expensive when I researched it back in 2015, and it departs from a relatively inconvenient port, not from a town you'd be likely to visit otherwise.

I can't speak to Puglia as I've not been there, but I always recommend Sicily to anyone who asks me about it. It was one of my favorite trips. I know a lot of people would say you need at least 2 weeks to visit Sicily but we only had one week and it was worth it. You can see a lot in a week as long as you don't plan to see the whole island. With a week it's best to stick to either the east or west and take your time exploring that piece.

Personally, I would keep your plans for May as I'm not sure anything will be happening regarding travel to Italy in January.

Thank you for your wonderful input. It looks like the consensus is to keep my original May itinerary of Southern Italy, and then do perhaps 2 weeks of Sicily including Malta. Maybe I’ll consider that for 2022 - depending on how 2021 plan goes.

acraven- the Malta ferry from Sicily cost around 65 Euros. I’m not sure if that was a RT or one way. I’m sure price will increase post COVID.

Is rental car necessary in Sicily? Or can I get by traveling via train?

Suki, just curious why you needed to come back to Rome for your return trip back home. Wouldn’t it be easier to go to JFK directly from Catania?

We've done a total of five weeks in Sicily (two trips), all on trains and buses. It can be done. It's slower than having your own car, so the more time you can devote to Sicily the better.

The ferry fare I saw was over 100 euros in 3015, but I was probably pricing it very close to my teavel date.

I wouldn't try to tackle Sicily and Malta in two weeks. That's really not enough time for a comprehensive visit to Sicily alone. I spent 17 or 18 days in Sicily and used public transportation. That was doable but not a fast way to get around. I ended up feeling as if I didn't have enough time at any of my stops. And I didn't go to any of the isolated Greek sights (Segesta, Selinunte, Agrigento).

I think you'll find budget-priced flights to both those destinations from elsewhere in Europe, so it should be possible to tack Malta onto a trip to a country other than Italy.

I agree with others - you have two or three separate trips here! I like your itinerary for your Rome, Naples...Puglia trip. Puglia and Matera are so worth a visit.

We have visited Sicily 3 times and really love travel there. You can easily spend 2-3 weeks there or 2 weeks in Sicily and another week in Malta.

Our most recent travel was to Malta for almost 3 weeks and then Ortigia, Sicily for 5 nights at the end of that trip. We flew Air Malta from Paris to Luqa Airport in Malta. Air Malta was a nice airline - I'd consider flying rather than the ferry. At the end of our trip, we flew Alitalia from Catania to Rome for our flight home. Can't absolutely recommend Alitalia but it's an option.

As far as weather goes, we were in Ortigia in early February, 2020. The weather was chilly at times but pleasant - some days we didn't even need a jacket (same for Malta). Some of the restaurants and a few shops were closed but the colorful local market was open. We thought that it was a pleasant time to be there - January might be similar.

A rental car isn’t necessary in Sicily, but does come in handy when visiting off the beaten path places like Caccamo castle, the salt farms at Trapani and Marsala, or Scala dei Turchi. A car can save on time by not having to depend on bus schedules, especially on weekends when fewer busses are running. When we were there, we picked hotels and B&Bs with free parking and near the sights we planned on seeing. Rather than driving in Palermo, we based ourselves in Monreale and took the bus into Palermo. The only places we paid for parking were in Noto and on Ortigia. I didn’t get any tickets or scratches or dents. You need to be an aggressive driver at times. Also, if you get a rental car, once off the autostrada, the roads are poorly marked, so have a GPS, or maps downloaded or offline use.