9 nights/ 8 full days of sightseeing in Sicily with a senior group in fall.

You might like to review the itinerary for the Rick Steves "Best of Sicily" tour and compare it to your own list of places and activities. You'll see some similarities, and notable absences, such as Ragusa and Modica on your list.

In particular, notice that they stay in 6 different locations, due to the geography of the sites being quite spread across the island. You also have fewer days than the tour: you have 8, whereas they have 9 for practical purposes - the first and last days of the tour not being full sightseeing days.

You may wish to begin by prioritizing your list and then see if those priorities can naturally group into 2 or 3 destinations.

Taormina is both intensely touristy and very expensive--though beautiful. I was ready to leave after a few hours. I would much prefer to stay in Ortygia, the historic area of Siracusa. That gives good access to Ragusa/Modica/Noto/Scicli. It is not a very convenient base for Mt. Etna (which can indeed often be seen from points like Catania), nor is it great for Taormina because of the travel time. And it should be noted that plenty of people love Taormina and are happy to spend multiple nights there.

Whether it makes sense to stay in both Taormina and Ortygia depends on what sights make your final cut. You have to weigh the time required to change hotels against the need for round-trip transportation to distant sightseeing targets. Getting close to Mount Etna, for one thing, is a fairly major time commitment even if you're staying in Catania or Taormina.

It's difficult to see a lot of Sicily if you're limited to two or even three bases. Honestly, what I'd do is reframe the trip as Eastern Sicily, Palermo and the West, or some other limited geographical area. Otherwise, I fear you're going to spend way too much time on the road. Two weeks is really the absolute minimum time I recommend for Sicily. I spent 17-18 days there and did not do these things on your list: Agrigento, winery, salt pans, cruise, opera performance.

I wouldn't want to skip Palermo because it is full of sights, but in the unlikely event you find you need to do that, Catania has an interesting food market.

I don't think you're going to have time for Trapani at all, but if you get that far west, I'd definitely prioritize Erice over the salt pans unless your group has a special reason for interest in the latter. Erice is a very evocative medieval hill town.

Thank you CWsocial and Acraven!

Looking at Rick Steve's itinerary, I see that they do 6 locations with 2nigh stays each. Over the years we have traveled, the only time we did 2-night stays was in Romania where we ended up staying at three different hotels. That was hard. Basically leaving out of a suitcase for the duration. As long as it's possible, i try to cut down on changing hotels with all the packing/unpacking. I think what the ladies enjoy most is to be able to come to the same hotel for a number of nights. It almost feels like coming home. You get familiarized with the area and it feels kind of nice. Kind of being like a local ;). I get the feeling that it would be quite challenging with Sicily though.

I realize that I will have to give up on quite a few interesting places because it just would not be possible to visit them all. I think our style is usually "visit fewer locations but spent more time at each". Quite different from the typical Japanese tours. To illustrate, the longest ones offered now are 8 days (6 nights / 5 full days of sightseeing). One of these has 6 one-night stays (Catania-Siracusa-Ragusa-Agrigento-Palermo-Taormina :)))

So, my goal is to see the best and minimize to 3 hotels. Palermo + Castello di Falconara + East side (Ortigia / Siracusa/ Taormina) OR the other way around finishing in Palermo.

For now, what I'm considering:
4 nights at Palermo (or Ortigia area if we fly to Catania)
2 nights at Castello di Falconara (perhaps one day or 1/2 day relaxing at the castle and the beach area...not swimming ;)
3 nights on the east side (Ortigia / Taormina / Catania need to work our where exactly)

Decisions. Decisions....

I think you're doing the best you can with the time you have. Traveling independently is very different from being on a tour with--key point--nearly door-to-door transportation. Even so, Rick's tours move too fast for me when it comes to the larger places that have actual sights to visit. I always feel I'd need at least one extra day (often a lot more).

Maybe the group will fall in love with Sicily, like many of us did, and want to return to see more.

Do you plan to hire a local driver and small bus? The interior of Sicily is interesting and much less touristy than the coastal towns. You'll be cutting through it if you shift from Palermo to Siracusa or vice versa, and a not-awful detour would allow you to see the magnificent mosaics at the Villa Romana del Casale.

If you go to ViaMichelin.com and plot a route between a couple of your destinations, then zoom way in, you'll see a lot of green lines in the interior. Those are the especially scenic roads.

First of all, I would underscore that your instinct to avoid 1 and 2 nighters is sound. I would start grouping destinations by what can be done from single bases. Monreale, for example, is very close to Palermo, so just plan a day trip there.
Mt. Etna pales compares to the significance of number of other sights, so maybe you can be satisfied with a view from a distance? I would also eliminate the idea of a cruise.

A picnic is easy to slot in somewhere. I think a winery visit and a cooking lesson may be very easy to arrange, especially the former. If you post a question here specifically about wineries, I think you’ll get lots of suggestions. Alternatively, look on TripAdvisor, but be wary of some of their ultra expensive listings.
We visited Villa Romana as a day trip from one of the other towns (can’t remember which). It was a longish drive, but tolerable. I would try to plot a route that puts it at a stop on the way between two other places where you will actually stay.
If you need to do any more elimination, Ragusa and Modica would be my next candidates.

Thank you, Acraven and Rosalyn.   
We will be using a private minibus transfer.  With a group using public transportation is usually more challenging, so we will hire a minibus with a driver.     

Initially, I was thinking 4 nights in Palermo (since our flight lands around 11pm).   Now I'm thinking of doing 3 nights and 2 days in Palermo so that we'd have more time on the east side of the island. 

Updated / rough ideas / broad strokes:   
day 1, arrive 11pm , check in, (3nights in Palermo)
day 2, full day in Palermo + welcome dinner (ca. 6.30 pm due to jetlag)
day 3, "A Day Cooking with the Duchess" (8.30 am-3pm) .... kind of a pricy cooking lesson, but I think for Japanese ladies that will be a unique experience having a cooking lesson with a duchess ;))   + marionette theater 45min show (not sure which one it is but I saw in one of the programs about Sicily ... maybe Opera dei pupi teatro Argento?? OR puppet theater in Ortigia/Siracusa?) 
day 4, check out, Montreal monastery,  transfer to Butera, check-in Castello di Falconara (2 nights)
day 5, Agrigento's Valley of Temples  (+ possibly Scala dei Turchi photo-stop,) relax at the Castello di Falconara
day 6, check out,  Piazza Armerina's  Villa Romana del Casale, (possibly via Caltagirone) to Ortigia/Siracusa or Taormina or Catania hotel  .....
Here is where it gets tricky...  Day 7, 8, 9...
day 10, depart, flight at 1 pm to Rome, on to Tokyo

We are flying out of Catania.   I do want to see Taormina and Ortigia/Siracusa. So, Catania would be logistically the best place to stay.  But  I understand that Catania is the least charming choice.    still not certain how to construct this so we don't end up driving up and down basically the same road so many times.   I understand that between Ortigia/Siracusa and Taormina it's about 125km or roughly 2-hour drive.   It's going to be a long day but we could still do a day trip from Ortigia to Taormina (or vice versa depending on where we stay).  

Is Catania really not recommended as a base?  I watched Rick Steves's  Travel Talk about Sicily with  Sarah Murdoch.  I kind of got the feeling that it was not her most favorite place.  She said something like "stick to the main street of Via Etnea because if you venture away from there, it's a bit of a reality check".  

Back to the drawing board...
        

I think your itinerary looks good. For your last base, I would stay in Siracusa. It’s a nice comfortable place, very walkable with many restaurant choices. You could day trip to Noto, Monica or Ragusa from Siracusa. You could also head north, with the motorway, you would make good time.

In our 2 week trip, we did not go to Taormina or Catania. We did not choose Taormina because it’s expensive and there is not much to see other than the theater. We flew in and out of Palermo.

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I think your itinerary looks good. For your last base, I would stay in Siracusa. It’s a nice comfortable place, very walkable with many restaurant choices. You could day trip to Noto, Monica or Ragusa from Siracusa. You could also head north, with the motorway, you would make good time.
In our 2 week trip, we did not go to Taormina or Catania. We did not choose Taormina because it’s expensive and there is not much to see other than the theater. We flew in and out of Palermo.

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Thank you Eef!

Now checking what's available in terms of hotels in Siracusa / Ortigia. Hopefully can find something. Taormina would be lovely to visit (not staying there as you are right it's expensive!!), but I am not sure if that is going to work with the itinerary. Now in a holding pattern waiting for answers from the airline and hotels.

Anna,
I too would recommend Ortigia. We are revisiting Sicily in late fall for 28N. We will be returning to La Via Della Giudecca in Ortigia. We booked directly with the B&B. We will be taking public transportation and starting in Palermo and flying out of Catania. As already mentioned up thread, a day trip to Noto, Ragusa and Modica is an excellent way to visit the Barogue Cities. Our B&B host arranged the driver.

Thank you Janis,

because we need like 10-14 rooms, I need to find bigger hotels that could accommodate us. Most hotels in Ortigia are on a smaller side and don't have availability for a group of our size _

Anna,
Sorry I missed the number in your group! I noticed you have several threads going on the Forum. With nine nights you may want to consider a base and do day trips. My sense would be to consult a travel company who could escort your group. It sounds like you have had good results with prior companies. Yes, lodging would be a priority. I just don't see how you could do everything on your wish list?

The first time we visited Sicily it was following a Southern Italy tour so we had about 10 nights in Eastern Sicily. Of course lodging and transportation was not an issue for just the two of us.

I hope you can find lodging and a tour to meet your needs. All the best.

Thank you Janis, I'm looking into travel agencies now. Hopefully I'll find someone good!

Anna,
Keep us posted. It's always helpful to share your results on the Forum for those who may have the same needs. ;)

Scala de Turchi should be easy to visit on the way to Agrigento as it’s only a few miles outside of town. There are a couple overlooks on the provincial road SP68 that provide a good view. The one I stopped at, that had a great view, was across the street from some supposed historic landmark that looks like a vacant building named A Marchisa.

Hello Everyone!  

​​​​​​​I hope my message finds you and your loved ones well.     The Coronavirus situation is like something out of a movie.  What's going on is just crazy.....  Here in Tokyo, we are all wondering whether the long-awaited Olympic Games will actually go ahead as planned.  

On a more personal level, I've decided to reschedule our planned October trip to Sicily to the spring of 2021.   I hope that this horrible situation comes to an end very soon.   We cannot wait to visit Sicily and wish everyone in Italy and everywhere else in the world strength and the best of luck! 

best, 
Anna 

Wise decision

Hi Anna,
Thanks for your follow up. It sounds like a well informed decision. All the best.
Grazie.

A correction:
Villa Romana Casale is in Piazza Armerina.

The baroque town of Noto is not far from Siracusa, much closer than Modica or Ragusa.
Can you add some more time to this trip? 9 nights/8 days is not enough time for Sicily. Is this the only stop on your trip from Japan? Three bases are recommended. I would not choose Catania as a base.
Palermo
Siracusa
Agrigento

Anna-

For another option in Eastern Sicily, consider staying in Acireale. I stayed there last summer in a B & B called San Sebastiano Holidays. The B & B was lovely (amazing host), the town is great, and it's close to beaches, Etna, Catania,... A much nicer place to stay than Catania. If you do stay in Acireale, check out Caffe Cipriani (very close to the B & B). It has amazing granita and arancini.

Happy planning!

Tracey

I haven't been to Acireale but want to mention that a Sicilian I met while waiting for the bus in Monreale recommended the town to me, and the photos look nice. Unfortunately, I had already been to the east coast of the island and didn't have an opportunity to visit Acireale in person.

Tracey,
We made reservations for this fall at the same B&B in Acireale. Of course this was made at the end of last year. We have resigned ourselves that this will probably not be reality this year. We also heard from Deborah, the B&B owner that Caffe Cipriani is famous for their Arancini. Deborah has been on my mind as I am connecting with people this week. I plan to write an email and send our support and hope her and the family are doing well. Thanks for sharing this on Anna's thread! Hello to Anna as well.

We loved Sicily in the spring because there was a surprise bonus of many, many wildflowers along the roadsides.
For us Taormina was one of our least favorite places. It is a beautiful setting but overrun. And we were in off season. On advice of our agriturismo we went first thing in the morning walked the length of the town took a few pics, grabbed a quick lunch and made it back to our quiet hideaway in time for tea and homemade cake . We were glad we went as it is beautiful j but a couple of hours was more than enough. Several other guests shared similar stories. Still some people don't mind tourist packed places that have beautiful settings and like to hang out . Just not us. So it depends on what you like.