3-4 Week Trip to Southern Italy. Puglia + Sicily or Puglia only?

I can speak only for myself: Most of our trips are about three weeks, three-weeks-plus. With that amount of time you could really cover much of Puglia, and a lot of Sicily. Especially since you prefer long-ish stays in one place, I would caution to visit only one of those two regions...

On our most recent visits to Puglia, we found three places new to us and enjoyed them each very much. Ceglie Messapica, Fasano and Nardó proved to be excellent bases that are located a bit out of the usual tourist path, lending themselves to day trips, and both, while small, are large enough to have some life in the winter months... Fasano and Ceglie, in particular, are rich in excellent restaurants. Galatina is also worth looking in to for a base..

Those are only two ideas based on our more recent trips to the region. Having so much time is great--leaves you time to explore the many sub-regions of Puglia and see some places that many tourists never get time for...

I travel solo, 78 plus, female, and travel to Europe 2 to 3 times a year for 5 to 6 weeks at a time. I generally focus on one area. So November of 2023 was in southern Italy for a month. Arrived Naples, then to the Amalfi Coast for a few days, Maratea, Tropea, Matera, Lecce, Polignano al Mare, and then back to Naples.

Especially loved Tropea and Lecce. Also took trips out from all of these cities where I was based. Every one of these towns that I had accommodations in was lovely, charming, some where especially small like Maratea and PAM. PAM might be only one I might have changed to Monopoli instead of PAM just because there were more historical attractions in Monopoli but it really was a toss-up.

Have already spent three weeks in Sicily and it just depends how much you want to see in southern Italy and all the other towns that I did not mention as I went there on day trips. And there is also Bari.

I love both Sicily and Puglia so much, and I can see how you’d want to visit both! We’ve spent 42 nights in Sicily in two trips and 40 nights in Puglia (including 3 nights in Matera) in three trips. Our two most recent trips to Italy were to Sicily early spring 2025 and to Puglia October 2025.

How much have you looked into driving times and flight times? For instance, driving from Matera to Messina (taking the car on the ferry, which we have done) takes at least 5 hours. Flying from either Bari or Brindisi to either Catania or Palermo is one to 4.5 hours flight time depending on whether you can get a nonstop or have to fly from Puglia back to Rome in order to fly to Sicily.

Were you thinking you’d stay in Lecce for the whole time you are in Puglia and do day trips? Certainly possible, but Lecce to Trani is about 2.5 hours, so I wonder if you’d want to stay in two or even three places — somewhere north on the water like Trani or Giovinazzo, somewhere in or near trulli country and within striking distance of Matera (like Ostuni, or maybe a masseria like Masseria Aprile, or a rented trullo), and somewhere south like Lecce or Galatina or Otranto. I guess that would argue for staying 4 weeks in Puglia and saving Sicily for its own trip, with an easy direct flight between Rome and Palermo or Catania. I do highly recommend Sicily in March/April when the wildflowers are blooming!

For “historical sites, hiking” I think Sicily has Puglia beat, but I’d still choose Puglia for over Christmas and New Years (avoiding primarily beach towns which seem rather dreary in winter).

More on Puglia: https://community.ricksteves.com/travel-forum/italy/recommendations-for-puglia