Sicily-Taormina vs Syracuse

I would stay more nights in Siracusa, followed by Ragusa. I enjoyed Taormina (it was very beautiful) but far too touristed and expensive relative to other towns in Sicily. Taormina is similar to Capri, if you've ever been - stunning views, elegant, exclusive, and lots of crowds. Ragusa turned out to be one of my favorite places (caveat: it is hilly, with an upper and lower town), and Siracusa has more things to see than the very compact Taormina. If you have a chance, also try to visit Noto for a half day. Noto is only an hour away from Siracusa.

I.would find 4 nights way, way too long in Taormina. I was ready to leave after a few hours. Two nights is quite short for Siracusa. Aside from the large historic area (Ortygia), there's a good archaeological museum and an archaeological park.

If you have 6 nights in Sicily, spend two nights in Taormina, 4 nights in Syracuse (staying in Ortigia).

Except that I don't exactly understand your comment:
The only things booked are flights in/out of Catania and **our last 3 nights (10/6,10/7,10/8) in a villa outside of Ragusa on the last.**

Does that mean you have booked your last three nights in a villa outside Ragusa?

Does that mean you have booked your last three nights in a - villa outside Ragusa? Yes, we have done that - about 6 KM to the east of Ragusa. I know the planning is a little in reverse but its a well booked 200 year old country estate that looked too good to pass up!!

GaryF

I think I missed that point that you're already staying close to Ragusa the last three nights. In that case, maybe stay the first night in Taormina, and then the rest in Siracusa. You can technically do Taormina as a day trip from Siracusa, but it may be more relaxing if you spend the night (or two) there. It depends how you feel about moving hotels after one to two nights. I don't think there's enough to do only in Taormina for more than a full day or day and half because it's very compact.

Two nights in Taormina (with maybe a short trip to the town above Taormina or down to Isola Bella), 4 nights in Siracusa (with side trip to Noto), and 3 nights outside of Ragusa (you could do a side trip to Modica, which is close by) sound pretty good for a slow paced trip.

4 nights Siracusa(at a minimum, all on Ortigia Island) and 2 Taormina ( at a maximum). We recently spent a week on Ortigia Is, the historic quarter of Siracusa) and could have spent much more time there.
We have seen Taormina and have no desire to ever return. Two nights was more than enough. Beautiful views of sea and Mt. Etna. Packed with day trippers. Cruise ship tours. Very over touristed. Ugh. Taormina has a totally different feel than the rest of Sicily. After walking Corso Umberto , the main pedestrian street, and visiting the Ancient Greek Theater, we took the gondola down to the beach area below to escape! The town is built on a hillside so you climb stairs constantly.
I am happy you are including a stay in Baroque Ragusa too.
We used Sicily Life for transfers from Ortigia to Taormina and Taormina to Catania airport, CTA.
I recommend them.
We toured the whole island of Sicily , driving a rental car, until we arrived in Siracusa and got rid of the rental car there. The food was outstanding, and we lived on delicious, fresh caught seafood with cannoli for dessert.

Regarding driving - I think our strategy will be to use transfers, private tour day trips on the first portion at least. For four of us, luggage, etc. we would need a dodge caravan size vehicle. The logistics of parking and navigating are a little concerning. I drove the same group in such a vehicle around in Ireland/Wales through some tiny roads and old towns, "wrong" side of the road shifting with my left hand. Somehow we managed to do it unscathed but wasn't easy. Not sure how much of that I want to do in Sicily.

2 nights in Taormina is sufficient. Then again, I feel 2 nights in Syracusa would be sufficient unless taking a couple day trips.

As others have said, I would allocate 4 nights to Siracusa/Ortigia and the other 2 nights near Taormina. If you decide to drive, I would recommend staying outside of the town of Taormina and take day trips to it instead. We stayed at a lovely old villa in Giardini Naxos then drove one day to Taormina, another day to Castelmola (could have combined this with Taormina in a single day, if driving) and a 3rd day to Mt Etna.

If you're not driving, then probably best to stay in Taormina to avoid some shuffling around.

We had 4 people plus luggage and rented an Audi A4, as I recall. It was plenty big, though most bags were sized for carry-on. I drove in Sicily with no problem - but then I lived in England for 3 years and am used to driving a manual on the "other" side of narrow roads and dodging cars and pedestrians. Our 2nd driver was a bit frazzled by the in-town driving and dodging. Town to town driving was just fine.

I also used Sicily Life for a transfer. My flight was a half hour early but the driver was there, spoke fluent English and had a six passenger mini van. ( He had driven a group to the airport.)

In Taormina, for the best granita, go to Bam Bar.

I agree with everyone else, Ortigia is much more beautiful than Taormina, fewer hotels and tourists and more history and just a nice place to stroll around, and you could do a day trip to Noto from there too
https://slowtravelitalyspain.blogspot.com/2019/06/siracusa-trip-report-october-2017.html?m=1

If you decide to drive, why would you need a large van for only four people? That seems like a much too large vehicle for four plus luggage.

If you decide to drive, why would you need a large van for only four people? That seems like a much too large vehicle for four plus luggage. Agreed - I am getting everybody to agree to one carry on size each + personal bag - so should be able to get into midsize or small SUV. Plus, we are doing Airbnb's, with most having washer/dryer so we can "refresh" some things as we go. When we did last trip in Ireland/Wales/Cornwall, each couple had a carry-on plus a 50lb oversized bag which necessitated a larger vehicle, not to mention back strain.

Things are coming into focus - after first 6 nts in Sorrento/Naples- We have a Flight to Catania 9/30 - xfer to Taormina - 2 nights - 1st day arrival just hanging out around town & relaxing - 2nd day - private tour - 3rd day xfer to Catania - do a short tour there and then to the airport to pick up a car - then on to Ortigia 4 nts, then 3 nts near Ragusa back to Catania to Naples on 10/9 the back to the U.S.A. 10/10.

From Catania and Ragusa we can do some nice day trips, maybe throw in a private tour or two. Started out totally "blind" but now starting to get a feel for the logistics based upon forum feedback and other research.

Should have said From Ortigia (not Catania) and Ragusa we can do some day trips

Just wondering why the transfer to Catania and then to airport to rent a car? Unless there's something specific you want to see/do in Catania. We'll be in Sicily in October and are planning a xfer from CTA to Taormina for a few nights, and will then rent a car in Taormina to drive to Ortigia, where we'll be spending 3 nights.

We thought about taking public transportation to Siracusa and waiting to rent a car until we leave that area, but even with the parking costs in Ortigia, it is still almost the same cost to rent a car days earlier as to wait until we're there and ready to continue on. Crazy, huh?

With the caveat that I haven't seen much else in Sicily besides Catania (where we flew into), Taormina, and then the medieval villages above there of Savoca, Castelmola & Forza D'Agro, I think folks are giving Taormina a little short shrift here.

We loved it, for four nights. It was admittedly our first trip in Italy--we flew into Rome, then immediately on to Sicily. We stayed at Hotel Villa Schuler, just off Corso Umberto, the main drag. And we had a wonderful time--this was October 2010--just wandering, exploring the little back streets, and admiring the Teatro Greco.

Sure, it's touristy, but it was not overrun that time of year, the restaurants are top notch, and the scenery is spectacular. What's not to like?

Next trip, we will stop in Taormina, but will continue on for a few nights in Cefalu, which looks wonderful, before flying out of Palermo.

Gary, lucky you guys, visiting Sicily!
When in Taormina, I enjoyed a few hour side trip up to the ancient hill town of a Castelmola, maybe a 15-minute uphill drive from Taormina. Very small stone town, a castle (which was not open at the time we were there), some lanes with homes, shops, etc. interesting almond wine to sample, I then got a bottle. Great views down. Nearby, where you can easily stop during the drive up or down, is a unique church carved into a rock (open when we went by, don’t know if there are regular hours). From the area in front the church, there is a wonderful view looking down over Taormina, including its ancient theater. This was a nice variation from the resort feel of Taormina itself, which I also thoroughly enjoyed. Our group of 4 or 5 just hired a largish taxi to take us up to a Castelmola, stay for about 2 hours while we wandered around, then take us back, with a stop at the church. You could arrange a car/driver, no doubt. There is also a local bus route up there, but you would give up a lot of flexibility and comfort that way.

Just wondering why the transfer to Catania and then to airport to rent a car? Good question - We resolved, based upon a little research and forum advice, that it would be better to spend less time in Taormina and more time in Syracuse. So, as we are arriving in Catania airport 11:30, it just seemed more relaxing to get a xfer to Taormina and hang around the town that first day, book a private tour w/driver the next day and then pick up a car on day 3. On the xfer to Catania, we will do a little tour of the town, have some lunch then over to the airport which is South of the town center and looks to have easy access to the motor way that will take us further south to Ortigia/Syracuse. So, we can get "lay of the land" the first couple of days with someone else driving and then take over the wheel on day 3. I think had we decided to spend 3 or more nights in Taormina, we would have chose to rent the car directly. Looking at Ortigia vs Taormina, my sense is that both are beautiful. Perhaps if you were just doing a beach getaway (water may be chilly in Oct), maybe Taormina might merit more consideration as it looks like more of a seaside resort destination or at least that's my impression whereas Ortigia has a lot more to offer. Another important "key indicator" for our group - I put a search on TripAdvisor for best pubs in each of Taormina and Ortigia - just 2 listed for Taormina and 25 listed for Syracuse.