Would you suggest starting in Catania area or Palermo?

Have you considered a guided tour of Sicily? There are companies that do this beautifully, I did a bus tour 2 years ago and loved it. Leave the complicated logistics to the tour company. You will find it a very relaxing way to enjoy your trip. Besides is not an easy self guided destination especially with a group.
Private email me if u wish some names of tour companies that run tours. Your time to visit is ideal.

Hi Anna,
$260 a night for a twin does not seem reasonable at all for me. Surely you can find something cheaper. How many are in your group? I travelled all around the island of Sicily last September - October with a friend and we paid in the range of 58-90 euros a night for twin and triple rooms. I found prices in Sicily to be very budget friendly.

With regards to flights and a route going east to west or vice versa, I would go with whatever works best with my overall itinerary pricewise and timing wise. What airport are you coming from prior to Sicily and where do you go upon leaving? For me the best flights by price and time would end up determining the direction of my route.

What are the places that you want to visit and how many nights are you planning to stay at each place. Do you need twin and triple rooms? That will help us suggest a good route and may generate suggestions for hotels/bnbs.

It sounds like you are considering a visit to Siracusa/Ortygia as a daytrip out of Catania. I think many folks would recommend actually staying at least two nights in Ortygia. There is a lot to see there and it is all beautiful. Ortygia is a short bus ride from Catania. I liked Catania but I liked Ortygia even better. Taormina could be done as a daytrip from Catania but it depends on your route. Also Catania is convenient if you plan to see Mt Etna.

I looked up Castello di Falconara because I am unfamiliar with it. Pretty scenery but its location on the coast impacts your travel route too. How many nights do you plan to stay there? Do you plan to visit any sites from there? Maybe do a daytrip to Agrigento from there? If you are committed to Castello di Falconara then I think your three bases will be Catania or Otygia, Castello di Falconara and then Palermo. Again the order of the visit for me would be determined by convenience and cost of flights.

With only 9 nights you will have to prioritize the places you want to visit. How are you travelling from place to place? Will you have a driver, or a bus for your group or depend on public transportation? I would think that getting to Castello di Falconara from either Catania/Siracusa or Palermo will not be easy on public transportation. I assume your group will have a driver otherwise you need to factor in travel times that will be longer and less efficient.

Hope these ideas help.

Thank you, JS. I will definitely need to use a trustworthy bus company/someone who can provide us with a Japanese speaking guide because the ladies don't really speak English which always makes things more complicated. Not that many Japanese speaking guides in Europe and they are so expensive. Once I have a clearer understanding of where we are throughout the itinerary, then I'll be getting transportation, etc arranged. I am a bit of a nut when it comes to how we put the itinerary together. Way back when we started traveling to Europe (that was in 2012 to Russia), I realized that companies dealing with Japanese tourists are really set in their ways (i.e. "Japanese people like this...don't like that... etc etc). and that was always going against my ideas, so since then I've been trying to take care of as much as I can about our itinerary myself ;))

Your hotel price range is way, way out of my league. But I haven't stayed in 150-euro hotels in Sicily, either, so I am in no position to assure you that one of those would be fine. My standards are rather low (clean, conveniently located, private bath, Wi-Fi, air conditioning). I can well imagine that at least some of your clients are accustomed to the finer things in life. And Rick made an interesting comment in one of his videos: When he visits a challenging location, he likes to make sure his lodgings are truly comfortable. I'm nearly certain he was in Palermo at the time.

In terms of how to structure the trip, all I can contribute is that Palermo is a hectic city with an inadequate number of traffic signals. You must keep your wits about you when you are crossing a street, and for people with mobility challenges it could be an extra concern. I haven't been to Japan, but in my imagination it is a very orderly (though often crowded) place. So all other things being equal, I'd position Palermo last. The cathedral at Monreale is an outstanding sight, so that's an opportunity to end on a high note.

Hi Anna,

I agree with others regarding the cost of a hotel. I haven't been to Sicily, but €260 a night for twin rooms seems ridiculously high. If you haven't already, your might try Booking.com and/or Hotels.com and do a bit of comparison shopping.

I'm also planning a trip to Sicily - but mine will be for my birthday in April. As you said, where to start is a personal preference. I'm planning fly into Palermo for a few days, then take the train to Catania, and from there, either a train or bus Siracusa. I'm planning to fly out of Catania. I'd like to do Palermo first, then relax in Siracusa before heading back to Trieste. It really depends on how you'd like to start and end your trip. I like to go for the bigger city first, then wind relax and wind down.

Hope that helps.
Theresa

I don’t know the size of your group but it seems like you have a very complex task. Arranging hotels, transportation, getting a Japanese speaking guide - just to start. I think what you must do is use a travel agent to book this trip. Depend on their knowledge, contacts, efficiency, pricing and the ability to fill your specific needs.

Thank you Pat, thank you for such a detailed answer.  I apologize, I should have inserted a link to my first question regarding the itinerary which I posted a while ago.  I just thought I should ask about hotels in a different post.   https://bit.ly/2SlhXKO

We are traveling from Tokyo via Rome. The flights land in Palermo and Catania about 25min apart, so that is not a factor that would make much change.   Price-wise, still waiting to get Alitalia's quote.  I was told to expect it after Feb 7th. If the price is very different than it might be something to worry about. 

As to the bases.  Ideally, I would love to have 2 hotels which is what I usually try to do for our trips.  Even in Portugal last year, we only stayed in Lisbon and Porto (with a very long but still manageable transfer between the two).   I have seen that one tour from Japan does 2 hotels (Palermo + Taormina) splitting 6 nights.   This is by the way, the longest Japanese tour (8 day adn 6 nights), the rest have Sicily as part of an overall tour of Italy.  So they usually spend about 2 days in Sicily.   A couple of my ladies even said: "are we only going to Sicily without adding anywhere else?"   So in general, 8 full days and 9 nights is considered long for Japanese travelers.   

Logistically, having a stay at the castle might make things less smooth.  But in all of our travels, we have never had an opportunity to stay at a castle!   And unless we do it as a group (since it's expensive), once again we'll miss this chance.     I guess I have to give up on some other things in order to make this work.   

Hi Acraven,

I hear you! When I travel with my sister, we stick to much more affordable accommodations ;). 260EUR is a lot. Even for a group. Throughout our previous travels, I'd say our average rates never went over 200EUR and we stayed in Madrid and Vienna. So, accommodation in Sicily I feel overpriced for the hotels (at least what I see online and in photos). You can stay for cheaper and some very nice hotels in Tokyo and Tokyo is considered one of the most expensive cities!

Hi Theresa,

I've been checking Hotels Combined, booking, etc. You are lucky as your trip is in April. Prices seem much better in spring and early summer. And overall, I think to me that season looks like a better time to visit. Everything is green, blooming, fewer people. But alas, for us it's Sept / Oct.

Thank you Philip,
I am now looking at tour companies. Hopefully, I can find a good one.

Blockquote. I can well imagine that at least some of your clients are accustomed to the finer things in life.
.........When he visits a challenging location, he likes to make sure his lodgings are truly comfortable. I'm nearly certain he was in Palermo at the time.
In terms of how to structure the trip, all I can contribute is that Palermo is a hectic city with an inadequate number of traffic signals. ......I haven't been to Japan, but in my imagination it is a very orderly (though often crowded) place.
Blockquote

I wonder why Rick thought Palermo was a challenging location... and yes, you are absolutely right, Japan is very orderly, safe and clean!

Well, there were places in the city where crossing the street was challenging. And the city is by no means laid-back. It's a working city, not primarily a tourist destination.

You might want to watch the two Sicily videos from 2018 available on this website. There's some footage of Palermo in "The Best of Sicily". The comment I remember was from a much earlier video (perhaps "Travel Skills"). I don't know what Rick says about Palermo in the latest videos.