Recommendations for small towns in Southern Italy

Do you plan to have a car, or use public transportation?

We are comfortable with either.

I love Matera, the historic center has a great small-town feel. Not far are some of the hill towns of Puglia: Martina Franca, Ostuni, Locorotondo. About ten minutes' drive from Alberobello (too much neon for me) is a small trullo B&B called Podere Papilio, wonderful hosts, great breakfasts with home-made jams and preserves from their orchard.

If you would go as far as Sicily, I can recommend Sciacca on the southwest coast and Cefalu on the north coast, east of Palermo. We spent 5 days in each (6 nights) last September and they both fall into your criteria. It's a little more difficult to find decent apartments in Sciacca as it still retains its charm as a real working town for the most part. A heavy concentration of ceramic shops in part of the downtown area but tons of commercial fishing. Very authentic.

Tropea (on the southwestern coast) has a lovely, promontory setting and beautiful beaches.

Sicily would be great for you. I wrote a very detailed trip report. Of the places I visited, I think you'd love either our agriturismo in Caltanisetta or our apartment in Ortigia (Syracusa is a city, but the center feels like a small town). Details here: https://community.ricksteves.com/travel-forum/trip-reports/sicily-palermo-caltanisetta-siracusa-taormina

I've enjoyed Sicily twice with our group tours. Rick doesn't cover this area in his Italy book, but you can get some ideas from the tour itinerary. Lonely Planet and Michelin Green Guide are other guidebook series that I've found useful.

Agree that Sicily meets your criteria. In late April 2013 we spent 4 weeks there driving a circuit of the island. In your case, you could pick 3 towns and do day trips to see the various sights. We also loved Sciacca but we stayed at a B&B. Sciacca is near many sights and has great sea food and the best Cassata Siciliana in all of Sicily. Ragusa Ibla or Ortigia are other towns where you could stay several days and do day trips. Cefalu would be nice and you might also want to spend a few days in Palermo. As we were driving around the entire island we moved quite a bit in our 28 nights, staying in 11 towns for between 1 night (2 towns) to 4 nights (2 towns). In researching Sicily we searched for 1, 2, and 3 week itineraries and then researched the sights mentioned. Tripadvisor Sicily forum was very helpful. Everyone we meet who has been to Sicily raves about the food, even Italians! It has historical sights and ruins and great scenery. And the people are very friendly. Unfortunately we loved everyplace we visited in Sicily which makes helping you with recommendations very difficult!