Off the Beaten Path in Sicily

Can you tell us where you’ll visit on the tour? It’s kind of hard to get a sense of your timeline, though I’d recommend flying open jaw Catania/Palermo in most cases. Traversing the island isn’t the easiest thing to do. But depending on how much time you spend in Palermo for instance, it might be worth it.

Also… impressions. Sicily in general feels a bit smaller or backdoorsy than the mainland. For instance, Ortigia felt very local and small town and is a tourist “hot spot.” I was in Noto for the flower festival, and with peak crowds it could feel empty. An overnight stop midweek in Piazza Armerina found the town pretty much dead. Just saying, some of these small towns in Sicily are REALLY small towns and slow with a capital S. You might not need to work as hard as you’re imagining to get that authenticity.

My admittedly limited experience in Sicily was that the most backdoor-ish places were the little hill towns in the interior. But outside of Ortigia, I think we had a pretty low-key, pretty "Sicilian" experience in Sicily. Whether that was because it was late October/November or that's just the general vibe is hard for me to say.

https://www.theroadreel.com/small-mountain-towns-in-sicily/

A few years ago I took a train from Messina to the small seaside town of Oliveri. The town is quite small and was pretty empty in September. I stayed there as it had a train station and was close to Tindari. The purpose of my stop was to visit the shrine of the black Madonna of Tindari. The sanctuary sits high on the cliffside overlooking a beautiful beach and the sea. Since we didn't have a car we arranged with our BnB owner to drop us off and pick us up. Tindari was originally a Greek settlement, later invaded by Romans. There is an archaeological park there walking distance to the sanctuary, with ancient ruins, although it is not as impressive as the major sites. From Oliveri we caught a train to Caefalù.

If you like Sicilian pottery then consider a visit to Santo Stefano di Camastra. As you get closer to Caefalù you could consider Caccamo or Castelbuono. Both are hill towns and have castle ruins but don't fit your wish for a beach.

Milazzo, which sits on a peninsula jutting into the sea, appeals to me although I have not been there. It is not far from Messina and might fit your wish for a relaxing, lesser touristed town. In Messina, hopefully you can explore the area, street, house or church where your ancestors lived.

Which airport gives you the best exit schedule and price, Palermo or Catania? If you head back to Catania, you might choose to explore some of the Aci towns.

What about the Nebrodi Mountains, a national park, reachable from Messina?

Or the Madonie Mountains, between Messina and Palermo?

The Aeolian Islands would also be a natural fit; you could take a fast ferry from Messina to Salina, for example.

We visited that island twice in the past few years, and really loved it....you can rent a car for a day or two, or get around by bus/driver. Chance for swimming, hiking, wander around picturesque port towns, take a wine tour or a "capers" tour.... We stayed in Malfa on both of our trips....

We loved Polizzi Generosa at the southern end of the Madonie mountains and would have loved the opportunity to go higher.

Yes, Santo Stefano di Camastra for their unique orange and red pottery. And medieval Randazzo is a great town to visit or to stay in as we did --- it was our base near Mount Etna and for day trips to Bronte to buy and eat pistachios and pistachio products, and to wineries.