Sicilian itinerary

Doable, certainly, particularly if you’re driving. There aren’t toll roads in Sicily, and driving is relatively easy. Finding parking in smaller towns can be more of a challenge,

For Day 4, if you’re looking at Ragusa or Modica, I’ve not been to the former, but highly recommend Modica. It’s a stunningly beautiful, with a higher and lower town, connected by stairways. The chocolate shop in the lower town, dedicated to preserving the Aztec-style chocolate that was originally introduced to Europe, before milk chocolate and Dutch cocoa became the norm, is wonderful. Both trips to Sicily gave included stays in Modica.

For Day 8, if you’re not looking forward to beach time, consider a night in Caltagirone, between Agrigento and Siracusa. It’s in the interior, and is famous for its tiles, and the long, tiled staircase that runs through the center of town, with no two steps the same. We stayed at the top of the town. On the way from Agrigento, be sure to visit the Villa Romana del Casale near Piazza Armerina. It was a big shot’s palace from Ancient Roman times, and features incredible mosaic floors and a very long hunting scene on a very long wall. It’s one of the premier historical sights in Sicily.

I am really not interested in Greek and Roman ruins, though I make an exception when there are mosaics to drool over. Therefore, I haven't been to Agrigento. I suspect you have considerably more time there than you'll need; I don't recall any other itineraries posted here that included 3 nights there, and maybe not even 2 nights.

I agree with the idea of transferring some time to the interior of the island. Piazza Armerina looked attractive when I passed through it on the way to the Villa Romana. Enna had a nice, no-foreign-tourists vibe.

I thought all of Noto, Modica and Ragusa were worth seeing. There's also Scicli in that area.

Note that things can shut down for many hours of the afternoon, especially in small towns.

Last September, we had a wonderful, self-drive trip to Sicily (and then Rome), as follows:

Fly (from US) to Rome to Catania, drive to Taormina via Castelmola, sleep Taormina

Drive to Etna wineries and back to Taormina, sleep Taormina

To Ortigia, sleep Ortigia

To Ragusa via Noto, sleep Ragusa

Drive Ragusa - Modica - Scicli - Donnalucata, sleep Ragusa

To Agrigento via Villa del Casale, sleep Agrigento

Agrigento to Scala di Turchi and beach, then Valley of Temples in PM, sleep Agrigento

To Cefalu’, sleep Cefalu’

To Palermo via Monreale, sleep Palermo

Palermo, sleep Palermo

To Rome

Most everyone recommends against moving frequently but this worked great for us. Honestly, cannot imagine spending three days in Ortigia…not that we did not like it, we did, but no need to linger. We typically do not make return trips in lieu of seeing more of the world but would love to return to see more of Sicily. Enjoy your trip!

Thank you everyone for these great suggestions, so helpful as usual!