Sicily trip April 13 - May 10, 2022 - Is this a good plan?

Sounds like a wonderful plan! I've traveled in Sicily twice in the last 3.5 years, and especially love Ortigia/Siracusa. Ortigia is reasonably flat, with only a few streets having some slope to them, so your friend will likely not have any trouble getting around there. I would absolutely recommend Ortigia as a home base in eastern Sicily. There is much to see and do, at a slower pace, in that lovely neighborhood. I can't speak to the car rental situation, but do recall that a taxi from our hotel to the Catania airport took almost exactly one hour, early in the morning. If you do use a taxi - probably taxis, if there are 6 of you - you will want your hotel to book it/them for you, the night beforehand. Also, have you booked your flights yet? If your flight from Catania is ticketed SEPARATELY from your flight from (Rome?) onward to home, then you may want to consider flying to (Rome?) the night beforehand, staying in a hotel near the airport. Things happen in Sicily (weather, Mt. Etna's ash, for example) that could delay your Catania-Rome flight, and if your international flight is ticketed separately, you would lose that ticket.

Before the tour begins are you staying in the same hotel as the tour? Have you attempted to make reservations? Looks like the rates are non-refundable. After this past year I’m not going to book a hotel with a non refundable policy.

jmauldinuu, that is reassuring about the flatness of Ortigia. We have not booked flights yet, so that is a good reminder about separate tickets.
Sandra, I saw that the tour hotel (assuming it is the same on they would have used last year) is non refundable. We are looking at some nice airbnb apartments that are close to the tour hotel and even a little less money. That will also give us a chance to do a load of laundry before the tour begins.
Thanks for your replies.

Indeed, Ortygia is generally flat, and won't be difficult for your friend to get around, and Ortygia is absolutely wonderful, so he won't mind spending some extra time there. I would be thrilled if someone left me in Ortygia to relax for a few days.

Another vote for using Ortigia as a base. If you can’t get a hotel on Ortigia, get one in Syracusa proper. Another option could be Noto. When you reserve your hotel check to see if it has parking. There are a couple public lots just after you cross onto Ortigia. After crossing the bridge, make a left, go a couple short blocks and you’re there. When I was there in 2019, the parking machine only took 1 Euro coins, so ensure you have some. If you can rent a car in Siracusa and return it there, that might be best. Then, as suggested, arrange for a taxi or other service to take you to Catania airport. It is indeed an hour drive from Siracusa. A suggestion if you do actually drive there, have a GPS or use Google maps downloaded for offline use because once off the main roads, the roads are poorly marked. If you know which towns you’ll be visiting, plug them into your GPS or bookmark them on Google maps. Also look up where the public parking lots are in those towns and plug them in too. My GPS took me straight to the parking lots and saved a lot of time not having to drive around looking to them. Assume all parking will be paid parking. Some hotels in Sicily are within ZTLs, so ensure you ask how that works with a rental car before going over. For example, our hotel in Marsala was within a ZTL, but one could park their car for up to 30 minutes for loading and unloading. The hotel moved our car to a parking location. Finally, look up the speed limits in Sicily and don’t exceed them. Speed cameras are everywhere. If unsure of the speed limit, drive below what you think it might be.

The only iffy area I remember in Siracusa is the archaeological park, which is some distance from Ortygia. There's some up-and-down required there. Now, the little Baroque towns are not necessarily non-issues. Modica is built in a sort of ravine. Streets along the path of the ravine will be pretty flat. Turning left or right, things will change. Ragusa is built on two levels with a lot of steps in between. I'd research parking options ahead of time with a view to parking twice, once on each level. I think Noto will be OK, and probably Scicli.

Should we rent a car in Milazzo and return it in Siracusa or the Catania airport, or should we wait and rent a car in Siracusa for 5-6 day?

We took a bus from the Catania Airport to Milazzo and then took the hydrofoil/ferry to Lipari. When we returned (after 4 nights visiting Lipari) we rented a car from Europcar - the pickup location was a short walk from the ferry port (you can check the distance on Google Maps). We drove to Ortygia, spent several nights and then dropped the car off at the Catania Airport before our return flight. I think that would be easier to rent your car in Milazzo - according to Rome2Rio, the train or bus takes 4 hours vs. driving which takes about 2 hours. For our past trips, the flights from Catania leave early in the morning so we've stayed at the Catania International Airport Hotel the night before our flight home - they have a free shuttle which is convenient for an early morning flight.

When I look at hotel in Ortygia, most of them show already booked up for next May. Do you think they are actually booked, or is it too far in advance to make a booking?

I'd be surprised if hotels in Ortygia are booked up for next May - I'd keep checking as it may just be early to book. Two that we've stayed at (L'Approdo delle Sirene and Domus Mariae Albergo - edited to add: these are both very nice hotels that we'd stay in again but there are steps to climb to get to the rooms) do not have elevators which would be difficult for your friend. I'd check to make sure that the accommodation that you chose, doesn't have too many steps and/or that it does have an elevator.

Is Ortygia fairly flat?

I agree with others, Ortygia is relatively flat though some of the streets that go down to the sea (on the way to the Fountain of Arethusa, for example) are fairly sloped. Maybe your friend can avoid those or take a taxi to the waterside.

This sounds like a great trip!

Oh my gosh, I love this forum. Such a wealth of information! Thank you all for the replies and suggestions. It just makes the planning easier and better.

I agree that Ortigia is quite flat. Delightful base. You certainly won’t want a car when in Ortigia and Siracusa. Walking and taxis will be best there. Most taxis are minivans.

You can take a nice local bus to Noto which is hilly in parts.

Catania airport is about an hour away from Siracusa

The alcantara gorge park is on the east side and quite interesting. There is a lift to the bottom.

Also, there is a nice wash and dry laundry (they do it for you) just across the bridge leaving Ortigia. Easily walkable.

Re #4: If you look on booking.com for hotels for next May, you will see that many (or most) are labeled as having no availability. The first few times I ran into that, I panicked. Then, someone, probably on this forum, explained that hotels, especially where patronage is seasonal, typically don’t set their rates until after the 1st of the year. Don’t worry.😊

Dan, Thanks for the idea of using the buses for our day trips and the alcantara gorge and laundry tips.
Rosalyn, That is what I thought, so your input is reassuring.