3 weeks in Sicily-October 2016

You don't say how many nights that you will be spending in Sicily itself.

Since your flights to Sicily will be to/from Amsterdam(?), then I suggest you look now at SkyScanner.com and search which flight alternatives will likely be available to you for next October. Pick a weekday that you would be likely flying, and use a date for this November, as a reference point. Look into flying in/out of both Catania and Palermo airports.

For Sicily, I would start with three strong recommendations:

Open-jaw your flights, using Catania and Palermo for each point. Sicily is big, so your itinerary is best divided between these two airports.

Plan on renting a car. Many sites are accessed much more easily with a car. It also makes it much easier to explore wineries.

Plan on being car-less in Palermo. Either picking up or dropping off your rental car at the airport, outside of the time that you would allocate for visiting the city (and Monreale).

There have been some discussions here of late that might benefit you

https://community.ricksteves.com/travel-forum/italy/sicily-tips-for-time-and-travel

https://community.ricksteves.com/travel-forum/italy/sicily-tips-for-time-and-travel

https://community.ricksteves.com/travel-forum/trip-reports/sicily-by-public-transportation

I am in the midst of planning a 2-week trip so I can share some of my thoughts and research. A car will help you see as much as possible, but be aware driving is not fast so you will have to take your time.

We went to Trapani and the west of Sicily in 2013 for a week. You can cover Palermo, Erice, Mozia, the Egadi Islands, Segesta, Riserva Nationale dello Zingaro, San Vito Lo Capo. That's a week's worth if that area interests you. Maybe 3 nights Palermo and be sure to see Monreale, then 4 nights in Trapani with day trips although Roberto will recommend Scopello. I do not know how good a base Scopello is having not stayed there, but Trapani was a good base, easy parking, great food, access to the Egadi Islands.

My plan for 2016 is Taormina/Mt. Etna for 4 nights, Siracusa with day trips to Noto and Piazza Armerina (4-5 nights,) then the Aeolian Islands for 4 nights. BUT we will do this by public transportation.

Note the A-19, which cuts across the island from Palermo to the eastern part of the island, is closed due to a bridge collapse last spring. You will need to plan your route knowing this. Perhaps start in Palermo and go counter-clockwise around the island, or start in Catania and go clock-wise.

For wineries, I can recommend four areas that you can look into. So build one extra night in each of these areas, just so that you can roam with the car and hit two or three wineries to visit.

Near Palermo. Just south of Palermo are a string of great small wineries (ex: Calatrasi, near San Giuseppe Jato). Scopello makes a good base for exploring these wineries, as well as for visiting Segesta (and another winery: Ceuso). If you arrive in Sicily at Palermo airport, then you would book 2 nights in Palermo. Go back to the airport on Day 3 to pick up a rental car and book at least the next couple of nights in Scopello.

Between Marsala and Menfi. Good base for exploring Selinunte, the Trapani salt pans and Mozia, Erice (Erice can be visited from Scopello, if your base is closer to Menfi). Definitely choose an agriturismo as your base for this part! Donnafugata and Planeta are two of the better known wineries in this area.

Ragusa, Modica and the Val di Noto area. This is the one area that you should really concentrate on, IMO. Here it's an embarrassment of choices and a fantastic base for the Baroque towns, beaches, and wineries! Plan on a day just roaming between Comiso, Acate and Vittoria, if you're really serious about wines. Depending on where you choose to base yourself, you can either daytrip into Siracusa or choose to spend a night or two on Ortigia.

Taormina can be a base for a day spent roaming towards Mt Etna and wineries nearby. I personally would not choose Catania as a base for this.

This implies an itinerary arriving in Palermo, spending a couple of nights in Palermo, then moving west and south, before looping east. You would then leave from Catania Airport. In between Palermo and Scopello, you could build in a day or two in Cefalù. You will not want to keep your luggage in your car when you visit Agrigento or the Vila Romana in Piazza Armerina. So you will have to figure out where to spend your nights for these.

Not knowing how many nights that you have in total in Sicily makes it hard to give you better advise.

VERY important! You will need to e-mail the wineries that you want to stop in beforehand, just to make sure that you can visit. Many are by appointment only, but can be open to a more 'elastic' definition of this in the sense that the arrival time can be quite open (as long as they are expecting you). Be aware that the larger wineries tend to have set scheduled times for tours and Fall is their busiest season with groups. We have had very mixed results with drop-in visits, so it's best to plan in advance for the ones that are really important to you - by at least looking up their website and e-mailing.

Just to give you some idea, I spent 4 (very) full days in Sicily just concentrated on the southeastern Baroque towns plus Taormina. Since Sicily was a side-trip from Malta for me, I flew into and out of Catania (if you want to see other regions you should fly into Palermo and out of Catania or vice versa). Catania Airport had really good connections by bus to just about anywhere. I didn't have a rental car but used the local train and bus (so, for better or worse, the timing of everything was dictated by the bus/train schedules). I spent 1 1/2 days covering Syracusa and Ortygia, a 1/2 day in Noto, a full day in Ragusa/ Ragusa Ibla (my favorite of all), and a full day in Taormina before I looped back to the Catania Airport. It seems that Siracusa was a good base for the area but, had I to do it over again, I would have spent at least a night in Ragusa. I really wanted to see Modica too, but had to cut it out of the itinerary because everything took longer than I thought it would. Four days to see the Baroque towns was too short (because they were very long days that didn't end until well after 10pm) - I could have used at least 2 more days. There were so many beautiful churches, so I would recommend that region to you.

Some of my favorite places I Sicilia are: Palermo, Segesta, Monreale, Erice, Agrigento, Piazza Armerina (day trip to Villa Romana del Casale), Siracusa (day trips to Noto, Ragusa, Modica), Taormina, Cefalu. A good plan would be to start in Palermo or Catania and end with the other. A couple of museums worth noting are in Siracusa and in Palermo. Many archeological sites.

I had fabulous luck doing an internet search -- also was lucky enough to have had a nephew who was in the Air Force and married an Italian Girl and spent several years living in and touring all of Italy and Sicily! After years of going to Italy, my Dear Nephew talked us into Sicily and we both fell in love with this magnificent Island! Three weeks is a good amount of time for Sicily, as it's much larger than most people think. The Greek Ruins are spectacular!!!

I would choose a different "corner" of the Island for each week. For the East side (Messina, Taormina, Syracuse, Mt. Etna) I based myself in the beautiful town of Taormina - and spent a day in Taormina, a day touring, and so on........my husband wanted to never leave! Apartment rented through: legendofsicily.com He had lots of choices in his inventory, and in three trips, we've used everything from a small room in a BnB that he brokered, to a four bedroom house with a magnificent view of the Med when we traveled with friends. They also arranged a tour for me when I was there with two 60 year old girlfriends, to :Mt. Etna/Gambino Vini! Both in one day and very spectacular, and also a day trip all the way to the south to Syracuse. Some of his apartments have parking, and several friends have rented through this service and loved having their own car.

We have done this trip several times, and would do open jaw, fly into Catania (and go to Taormina) and fly out of Palermo if you're ending your trip on the West Coast. The Church of the Weeping Virgin in Syracuse is modern -- and totally different than any other church I've seen in Europe. The churches in Taormina are beautiful. Cefalu has a beatiful old Church. The Greek Theatre in Taormina is spectacular as are the ruins in Syracuse.

There's a spectacular church just outside of Palermo (name escapes me) but beautiful churches also inside of Palermo. Google it.

In Cefalu -- we had a "rest stop" for two nights at Hotel leCallette which had the most jaw dropping views I've ever seen - anywhere! We indulged ourselves while there and even had a massage, and went to town only once.

In Palermo we stayed at Palacio Centrale -- which is an old palace converted to a hotel -- and it is a grand old dame for sure.! We lucked out with a $100 a night booking through booking.com It was walking distance to Palermo's most important sites.

Next trip, I'm definitely getting to the West side to see the Valley of the Temples, and more "inland" excursions, including Amerinia.

I think the church just outside of Palermo that Donna refers to must be Monreale. Its beauty is breath-taking. The entire interior is filled with mosaics depicting Old and New Testament stories. The cloister pillars are each decorated with different mosaic patterns. Put it on your "must-see" list.