Hello Everyone! Bon jornu!

I am starting planning our yearly trip to Europe. We take a trip once a year as a group (between 13-18 Japanese ladies aged 65-83!) and traveling by charter minibus/bus. We've done Czech Republic-Austria, Hungary-Romania, Spain breaking it into 2 trips Madrid-Barcelona and Andalusia, Russia, Armenia-Georgia, and Portugal last year. This year, I set my sights on Sicily! We'll have 9 nights on the ground which will give us 8 full days for sightseeing. I am not counting the days we are flying to/from Sicily.

Seeing that the group is not young ) I don't like to switch hotels as much as it's possible. Ex. in Portugal we did 2 hotels (Porto and Lisbon) for 9 nights. For Sicily, I'd like to do 2 hotels (3 at the most). Checking with the airlines, it seems we can fly in and out of different airports (Palermo and Catania). The flights land around 22.30 / 23.00h. So there is no big difference which airport to start with in terms of arrival time. I cannot seem to make up my mind whether we should start in Palermo or leave it till the end of the trip. Or whether it makes any difference.

I realize that by limiting ourselves to 2 (or 3 hotels) only and because of the age of the group, we'll have to be selective in what we see and what areas we visit. We'll do one hotel in Palermo and one hotel near Catania (not sure what the best place would be yet).

We are interested in culture, art, history, food (so so much!!), wine, markets, shopping, natural beauty (but no adventures ). Not going to be doing too much outdoorsy stuff just because of the age gain--no swimming, snorkeling, climbing and such. That said, we love picnics, river/sea cruises, horse-carriage rides, etc.

Now I am thinking the end of September (from 20th on) till mid-October. I know you can never tell what the weather will be like, but as a general rule, I'd really like to avoid rainy weather because it's going to make it harder for older folks to walk. Since we are not interested in swimming, I'd rather visit when it's warm rather than hot.

Would you say mid-late September would be better than early-mid October?
Would you suggest starting in Palermo or on the other side of the island and working our way to Palermo?

Some of the places/activities I am thinking of including:
Agrigento's Valley of Temples,
Villa Romana del Casale in Enna
Monreale
Taormina's Townscape and Greek Theater
Ragusa and Modica
Mount Etna (not sure whether we'd do a tour or just see from the distance)
Siracusa, Ortega
Ballarò Market
Visit a winery preferably a small/family producer (tour + lunch)
Salt Pans of Trapani (possibly)
picnic (if possible)
cruise (if possible)
cooking lesson (if possible)
Palermo opera house (opera performance if possible)

I have a LOT of work ahead trying to figure everything out. I'd love to hear any advice or comments or recommendations!

Grazij!
Anna

Even for people traveling very hard, it is difficult to see the highlights of Sicily in less than 2.5 or 3 weeks, so yes, you will need to be very selective. With 8 or 9 days, the typical advice is to consider limiting yourselves to just the east OR the west of the island, but of course, other options are possible. And seeing even a select set of highlights from only two bases is extremely difficult -- as just about every thread on this very common question notes, Sicily does not lend itself easily to a base-city approach.

My very strong advice would be to (a) get a GOOD guide book or two (the Rough Guide to Sicily is excellent) and (b) please, PLEASE, read at least some of the MANY trip planning threads on this forum. You will find answers to many of your questions and ideas to consider that might make sense for you.

As for Sept. vs. Oct., personally, I'd go for Sept. because the days will be longer. JMO.

Sept is great
Rough Guide is very good.

Catania is "interesting" in a poverty-stricken way, though the ancient centre is fine (also the gardens are lovely). I might look at Ortigia (the cathedral is an ancient Roman temple which has been converted) as a second base rather than Catania but there are plus and minuses for both. Certainly, there are a lot of interesting things to see around Ortigia/Syracuse.

Thank you Kja and Bilboburglre.

@ Kja. The more I research, the more I see that I will have to eliminate a lot of hte places that I'd like to see because I'll have to stick to the plan of doing 3 hotels in 9 nights. I would have loved to have more days or to split Sicily in two trips, but that won't work. So, we'll only have 8 full days on the ground for sightseeing. (just as an fyi, for Japanese people 8 days just for Sicily is a lot ) One of the ladies said "oh, we are not going to add something like Alberobello? Just Sicily?" ) So that's the time frame I'm working with.

@ Bilboburgler. I keep going back and forth between Ortigia / Catania / Taormina. We'll have 3 days which I'd like to split for 1 day trip to Ortigia/Sicarus and 1 day trip to Taormina.. Logistically, Catania would make the most sense as it's in the middle and near the airport. But I am seeing somewhat discouraging reviews of Catania.

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).

If I was doing Catania I would focus on the centre and see if you can afford to book a small palace (October prices will amaze you for what you get for your $/Yen) then if the ladies want to stay around the old town they can and in luxury. You'll find the wine tours up the volcano are very pricy but the views are wonderful. I would not take the local train around the volcano unless they are tough old souls looking for a challenge, certainly cheap and second world in comfort standards. The gardens are famous and if your clients love gardens then.....

I would prefer Ortigia but I might stay in a hotel. The Island has enough to do on it for a day and then Siracuse temples have another day in them, so if you work hard you might do the lot in one long day.

I'm not that excited by Taormina. A bay with a cable car.

So my choice would be Ortigia.

Sounds like a great teachable moment!

The views from Taormina are stunning; the problem with Taormina is that it is so mobbed with tourists during the day as to be quite frankly unpleasant, and that means that if you want to see it with a large group of slow moving people, you might want to consider staying there. Frankly, I prefer Ortigia to Taormina, but the views FROM Taormina are, IMO, magnificent, and I far preferred the views OF Mt. Etna to the views FROM it. But then, your group is probably used to Mt. Fuji, and I'm not sure how important seeing Mt. Etna would be for your group.

If you are flying out of Catania and opt not to stay there, be sure to get a very early start -- no matter what the usual travel times, in Sicily, one needs to be prepared for unexpected delays. Or at least that's my understanding!

I'm realizing that hotel situation in Sicily isn't simple. Even for big cities like Palermo and Catania, the choices of 4 star (lower end 5 star) hotels aren't big. I feel that in Tokyo, there's a new hotel opening daily I'm still looking at Catania as a base. I feel that with 3 days out of which two days will be spent on day-tripping to Syracusa and possibly Taormina, we will only have 1 full day in Catania. Which probably would be alright if we stick to the charming center. I am sure Ortigia would be more charming but again the same things with hotels.

you mentioned possibly booking a small palace in Catania. I haven't come across anything like that. Any particular that come to mind?

I'm kind of now thinking of going in reverse: flying to Catania and out of Palermo. That is IF we can manage to find a great place to stay in Catania. As I wrote above, hotels seem to be scarce. Right now, I am checking with Palace Catania | UNA Esperienze (mixed reviews on that one). Anyone here has had any experience with this hotel?

I am thinking maybe it'd be good to:
day 1/ arrrive ca. 11pm, check in Catania
day 2 / Catania + welcome dinner
day 3 / Syracusa + Ortigia full-day excursion
day 4 / Short tour of Gambino winery with tasting & lunch (mostly going for lunch and views) afternoon tour of Taormina + dinner with a view of the sea and Mt. Etna in Taormina, return to Catania after dinner (maybe in the afternoon there will be fewer people?)

Then move on to :

day 5 / check out, villa Romana del Casale (perhaps with a stop over Caltagirone to see the stairs OR maybe skip everything but Villa Romana in order to have more time to enjoy the Castello di Falconara), Castello di Falconare (check-in possible at 4pm)
day 6 / day excursion to Valley of Temples (possibly Stairs of the Turks photo stop), afternoon at Castello di Flaconra
day 7 / check out, Monreal Monastery, Palermo
day 8/ cooking with the Dutchess https://www.butera28.it/palermo-cooking-classes-sicily/ + Puppet show
day 9 / full day Palermo + farewell dinner
Day 10 / fly out of Palermo to Rome (at 12pm or 4pm) on to Tokyo.

The stairs are pretty, but I'm not sure they would be worth the time and energy to get there. I hope you realize that although the stairs are very old, and while the ceramic traditions of the area also very old, the stairway wasn't decorated with tiles until the mid 20th century. Or at least that's my understanding.

Leave plenty of time for the Villa Romana del Casale.

Good to know! I need to keep myself in check and keep eliminating places so that the itinerary is not constant hopping from place to place.

I'm guessing with so many people they may not want to share rooms/beds but you could look at

Booking.com and Le Suites del Duca di Sarro (I've never stayed but looks interesting)

or
AirBnB might have something. But I can see nothing. For that many guests I suspect it needs to be a hotel.

Based on hotel choices for that size of group I'd stay in Ortigia

European 4 or 5 star has no direct relationship with Japanese 4 or 5 star hotels. In Europe the stars are only based on lift sizes, guest to staff ratios etc. I've stayed in pleasant 3 stars happily. The issue may be more about, does the hotel have a spa that the group would like or any Japanese speaking hosts.

This hotel looks fine Algilà Ortigia Charme Hotel when I stayed next door in a hotel run by nuns (it had a pool) so you could split the group into the two hotels for example. (use Google Maps to find the name of the other hotel)

Yes I kind of getting the same feeling. I think some of the places I see don't really look like 4 or 5 stars that we'd see in Japan. My biggest problem right now is that in fact there are not that many hotels to start with. The most important is that the hotels would have TW rooms with 2 separate beds. we had a bad surprise in Madrid when they gave us rooms with Queen beds for guests who are obviously not related.

Many European beds that are Queens are actually two singles bolted together. I'd drop them an email and ask giving details of dates, numbers etc. I'd also drop Ortigia Tourist Information an email asking for assistance. Tourist Info in Italy is very parochial so Ortigia will not be the same as Siracuse (probably) so I would also check to see what Siracuse has as well (maybe a poorer position but probably with a bigger hotel). Ortigia looks like and wants to look like it is from the 1500s so the number of high rise hotels is very limited.

Thank you, bilboburgler! I didn't think of emailing the Tourist info for assistance. I should do that. I also noticed that most hotels in Ortigia are boutique hotels and thus don't really have many rooms. The hotel in Siracuse that seems to be available is the Hotel Mercure Siracusa Prometeo (not too excited about it. It looks a bit like a hotel for a business trip). Will keep checking...

Domus Mariae Benessere again looks nice, you may have to do a deal with a few of these hotels to get all your guests in, but as long as they are next door.