Sicily: BIG questions re 16 day on the ground itinerary

We really liked staying in Ragusa Ibla. It's so atmospheric. It's a lot less lively than Ortigia, though. I wonder if you could split four days with two in each place (??)

We'd been to Sicily a couple of times before but not in the past 15 years, so we returned in 2023 and went around with private drivers because my partner had difficulty walking (pre hip replacement). We had been to Palermo before, so this was our plan:

Fly JFK-FCO-Palermo...collected at airport by driver recommended by our hotel in Trapani, LA GANCIA.

Stayed in Trapani about 3 nights. Private tour to salt flats, salt museum. Dinners at some great restaurants--Trapani has no shortage of these. Recommend hotel.

Private driver from Trapani to B&B near Agrigento (did not visit ruins as had been before). Stop for lunch (fabulous) at DA VITTORIO, PORTO PALO DI MENFI (near Sciaccia) Stay two nights at BORGO DELLE PIETRE B&B, historic renovation of old farm buildings by the architect-owners. Recommend.

The two drives, above, were with. MICHELANGELO TRANSFERS.

Private driver (forgot name) arranged by B&B to Licata, where we stayed one night in order to have lunch next day at LA MADIA, fantastic restaurant, highly recommend as the best meal we ever had in Sicily.

From Licata, private driver ROBERTO ALABISO (highly recommend; fluent in English) to LA SABBINNIRICA B&B in Ragusa Ibla--highly recommend but there are some steep steps. Stopped on the way at MANDRANOVA olive oil producers, who also run a lovely-looking inn on the property. Stayed four nights in Ibla. From there on, hired driver DARIO CAFISO ( info@tourbarocco,it) for trips to: Chaiaramonte Gulfi for olive oil tastings at CUTRERA; and also to Marzamemi (you can skip) and for lunch in Porto Palo di Capo Pessaro You do not need four nights in Ibla, though.

From Ragusa Ibla, Dario Cafiso drove us to Catania; stayed two nights prior to having him drive us to Milazzo, where we boarded ferry to Salina. Superb hotel near Catania Duomo=PALAZZO MARLETTA, only about 6 rooms on two levels; one of best breakfasts I've ever had, as you order from a printed sheet the day before and they collect some things from great local bakeries--all kinds of things particular to Catania including the pastry named "Iris."

Dario is fluent in Spanish; fairly good with English.

Then driven to Milazzo for ferry to Salina. Stayed maybe 5 nights on Salina; loved it so much that planned trip the next year (2024) to spend more time on Salina.

Dario picked us up at Milazzo port, after return from Saliina, drove us to Taormina; spent about four nights there (had been before; not a tremendous fan as it's now overrun with tourists). Hotel VILLA BELVEDERE..highly recommend BUT rooms vary tremendously. Only space they had then was their apartment" down the street from the actual hotel.

That was a good place; even had a full kitchen we did not use, and terrace with Etna view (distant view)

Finally, driver to CAT for flight back to NYC.

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Did a different itinerary in 2024 but I did all the driving as we rented a car at Catania airport (SIXT) after spending a night in the city at same hotel. Spent a week outside Marina di Ragusa at SILVA SURI. Drove to Scicli, Marzamemi, etc. VERY EASY to drive in Sicily outside cities.

Then returned to Catania to drop off car at airport and stay one night.

Dario drove us to Milazzo, ferry to Salina and stay on the island about ten nights.

Dario again collected us at the port and drove us to a hotel outside Siracusa that had a shuttle bus to Ortigia.
Stayed at that hotel a few nights before flying from CAT to Munich, on Lufthansa. After five nights in Munich, flew back to JFK direct.
Sorry for the looong post....hope some of that is relevant1!!

I have been to Segesta and Erice, not Salinunte. Erice is one of my all-time favorites, and I liked Segesta more than Agrigento. Staying in Trapani (as I did) is a good idea as it has public bus lines to both sites. Trapani itself felt bland, but I went there after a week of visual indulgence in Palermo!

I stayed in Siracusa/Ortiga for 5 days and did a day trip each to Ragusa, Modica, Noto, and Scicli. All incredible for Sicilian Baroque architecture. There is an old-school railcar line that connects Syracuse to all these towns. However, it takes almost 2 hours to reach Ragusa. There may be bus routes that I didn't look for. Many people like to stay in Ragusa.

Catania is fine, and good place to take the Circumetnea train to visit towns like Randazzo with its black lava stone churches (another favorite). Went to Piazza Armerina (stunning town center) and the Villa Romana del Casale from Enna. I believe a day trip from Catania is possible.

Didn't go to Taormina because it seems overwhelmed by tourists. I got my amphitheater fill elsewhere. Last stop in Sicily was Messina, primarily, to see the two Caravaggios in the museum there.

Sicily is still at the top of my list of destinations. You will not be disappointed no matter where you go.

Your trip sounds similar to the trip that me and my spouse took to Sicily in 2018, except we only had 12 days in Sicily. Our focuses were ancient ruins and mosaics. We did rent a car as we left Palermo, and drove (counterclockwise) until Ortigia, where we dropped off the rental car after our second night in Ortigia, then took a train to Taormina. Then a cab from there to Catania. We didn't spend any time in Catania, other than to fly out to Rome.

Monreale, yes definitely. Also the Cefalu Cathedral, but I enjoyed Monreale more.

Yes to Segesta and Sellinunte, especially if you like ruins, but we had a rental car. We picked it up leaving Palermo, and spent that night at a gorgeous wine estate in Menfi.

We spent two nights in Agrigento, and spent most of our full day there in Valley of the Temples.

We spent two nights in Piazza Armerina. Our full day here was an all-day tour through Passage to Sicily, which was very special for me. We visited Villa Romana, which was everything I thought it would be, though this was not the part of the day that I felt we needed a guide for. I would say that if you are in Sicily, you should visit the Villa Romana; the mosaics are superb. The guide was more for our visit to Morgantina, which is from pre-Roman times, and very ruinous. Not everyone would appreciate this site because it's so ruinous, but it was a must-see for me. Just as important, we also visited the Museum Aidone (with the guide). This museum holds the "Goddess of Morgantina," from the 5th century BC. It was repatriated to Italy/Sicily by the Getty Museum in 2011, and I really wanted to see it in its home locale.

We spent three nights in Siracusa, specifically Ortigia. Another location I wanted to visit due to its importance in history. We visited the Greek Neapolis, of course. And did a day trip to Noto, which was more interesting than I thought it would be. So easy to do day trips from Siracusa, though I don't know how you would do that without a rental car, because we had the car.

We ended with two nights in Taormina, which I've got to say is a gorgeous town, with magnificent views. Our highlight here (to me) was a day-long tour of Mt. Etna. The guide picked us up in Taormina, and we did some hiking on Mt. Etna. The views were not perfect, due to clouds obscuring the summit and recent volcanic activity, but still awesome. Our visit to the Greek Theater in Taormina was also nice.

Enjoy your planning, and your trip!

Don’t miss Villa Romana! We had a rental car in Sicily and highly recommend that you do the same. We started in Palermo and covered Sicily, ending in Taormina, the only place we disliked.
Our favorite place was wonderful Ortigia where we stayed for a week in a waterfront apartment. We recommend Ortigia highly!

https://community.ricksteves.com/travel-forum/trip-reports/14-days-in-sicily-by-bus-train-and-car-in-may-but-with-november-weather

Here is my trip report of Sicily which may help you. We considered using private transport between the east and west sides of the island but opted for renting a car. Five days with a car was the same price as one day of private transport.