Hi, trying for an October trip for 4. Days cannot be too crazy due to 76yo and 10yo. We plan to rent a car when leaving Palermo and follow the don't leave luggage in the car advice. Any thoughts on whether it works better to have place you are departing from keep luggage for the day, or to show up early and have luggage held? Also appreciate any thoughts on whether it makes more sense to drive a little more so one doesn't have to move hotels as many times. Any thoughts on trip in this order versus in reverse? Length of trip 2-3 weeks. Currently close to 3 weeks, if I want to shorten: (1) cut night at Ragusa? (2) 1 night at Agrigento or could this be day trip from Enna (go from Segesta to Enna)? (3) each of the Greek sites seems unique in its own way, but should I cut one of them out? Or just go for it, it will probably be Mom's only trip to Sicily. Thanks for any input.
Day 1/Day 2/Day 3: Arrive Palermo, Walk and tour Palermo, Tour Monreale Cathedral
Day 4/Day 5/ Day 6: Drive to Trapani/Erice or Segesta (thoughts on which would be better to stay?), Tour Erice, Tour Segesta, Tour Selinunte
Day 7/Day 8: Drive to Agrigento, tour Valley of Temples and Museum
Day 9/ Day 10: Drive to Enna, Tour Enna, following day drive through some mountain towns, Sperlinga, Soprana.
Day 11/ Day 12: Stay in Enna or Relocate to Piazza Armerina?? Tour Villa del Casale, following day Caltigirone & ceramics shopping.
Day 13: Drive to Ragusa? In my reading to date, this struck me as most interesting Baroque town (maybe it was the few photos I saw, not sure). Not sure how interested we are in Baroque. Keep? Skip? Does one see enough Baroque in Ortygia? Should we just drive thru one of the Baroque towns?
Day 14/ Day 15: Stay Ortygia, Tour Syracuse, Museum, Ortygia.
Day 16/Day 17: Drive to Taormina, See something in Taormina, next day Mt. Etna tour of some sort.
Day 18/ Day 19: Drive and stay in/near Montalbano Elicona (family research & visit).
Day 20: Depart Palermo.

Sicily is delightful, and it's nice to see someone plan to give it a reasonable chunk of time! Some thoughts:

• Depending on your interests, you might want more time in Palermo. Its a place filled with things to see and do, and even at a very hard on-the-move-every-possible-moment, I found 2.5 days insufficient to see its highlights.
• Depending on your preferred travel pace, days 4-6 may be overly ambitious.
• I thought Enna interesting, and saw pretty much everything there is to see there in less than a half day. And IIRC, the road into and out of Enna is a bit of a challenge, so I wouldn't base there. YMMV.
• I'm not a great fan of the Baroque and so skipped most of the Baroque towns. I did visit Noto, and even though I don't usually like Baroque very much, I absolutely loved Noto -- the stone is a wonderfully warm hue and the decorative elements have a decidedly humorous twist. You can visit Noto by bus or train from Siracusa / Ortigia.
• Again depending on your interests and pace, your time in Ortigia might not be quite enough.
• Taormina is beautiful, but truly unbearable during the days, when hordes of people visit. Be prepared and plan accordingly!
• There are two kinds of visit to Mt. Etna -- one takes you to (or more exactly, very near to) the top. It requires multiple changes of transportation, and you would do well to be prepared for the top with thick-soled shoes, protective eyeglasses, and clothing that will protect you from the winds, which can be very strong and surprisingly chilly. The other type of tour of the area is to visit wineries on the slopes of the volcano -- obviously, a very different thing. Make sure you know which you want.

As for the logistics:

• Before deciding about leaving the luggage after or before your stay, make sure your accommodation will have staff on duty at the time you'll want to claim it.
• As a solo traveler, I prefer to relocate rather than backtrack, but I think I'd feel very different about that if I were traveling with 4 people of vastly different ages. In that case, I think there would be a lot of advantages to limiting the number of different hotels required for your plan.

I hope that helps!

I wouldn't go to Noto by train. We did, from Ortigia/ Siracusa. The train station is a distance from the town and its all up hill into town, a bit of a slog for your Mom, I would think. We wasted alot of time waiting around for the bus to return, and ended up with a very old and beaten up taxi ride back to Ortigia, not recommended.
Noto is really pretty.