2 weeks in Sicily - need advice on splitting time

I never know if I should answer questions when the initial premise is so far from the way I travel. I find the idea of "bases" even less workable for Sicily, which, for me, lends itself best as a "road trip". But, if it might help you at all, I will give you my opinions.

I don't consider Ragusa a day trip from Ortygia nor the Aeolian Islands from Catania or even Taormina. Its not really that I think the idea of "bases" is wrong, its just that, in general, I won't do a day trip that involves more than 2 hours (usually less) of drive time especially when its by car. But, that's my style, and not yours. We spent a full day in Noto which we did via train from Ortigia. I can't imagine trying to do Noto, Ragusa and Modica in one day. You'd spend more time in a car than sight seeing.

Taormina hotel prices are much higher than the rest of Sicily. We didn't love Taormina, though it is a gorgeous place to spend a day. You could consider staying somewhere in the Mt. Etna area and doing day trips from there.

Have you thought about the expense of parking in the bigger cities? For Ortigia, you could consider using public transportation and rent a car for just a day to go to Ragusa. (about 3 hour drive round trip). You could pick up a car as you leave Ortigia to go north.

It’s common to see over ambitious itineraries proposed, such as how can I see all of Sicily in one week? This one actually is kind of the opposite, seeing half of Sicily in two weeks seems a bit under ambitious to me. Nothing wrong with slowing down or with the places you plan to visit, but you’re missing Sicily’s top three attractions IMO (Villa Romana near Piazza Armerina, Agrigento, and Monreale cathedral) as well as its best city, Palermo. While Ortigia and Taormina are both lovely and should be visited, they are the two most touristy places on the island, and I think that even with daytrips staying a week in each is too long. I was glad my Sicily tour stayed several nights in each of Ragusa and Catania, and just visited Taormina and Ortigia for the day.

I kinda agree with the previous two posters.

If the Falcone/Oliveri visit is important, you could just do that as part of unwinding and visiting the wineries on the north slope of Etna. Bear in mind, wineries are not like in Napa. For the most part, in Sicily you make an appointment in advance and the tasting often involves some kind of meal. There are some more touristic exceptions. You need a car for this area and maybe a driver on days you're tasting. We based in Randazzo but maybe you'll choose something closer to the coast. That area is really pretty but kinda spread out. You'll chew up a lot of time driving or riding around. The scenery is pretty awesome so it's hardly torture.

If Falcone is not important, then an itinerary that ties together better starts to shape up. Something like:
Ortigia 3-4, Hill towns 3, Agrigento 2, Palermo 5. Or skip Agrigento and
Ortigia 4-5, Hill towns 4-5, Palermo 5-6 with beach time
(You could substitute Falcone/North Etna/Taormina for Ortigia but you'll have more driving.)

But this is all just me and my biases based on one single trip. Sicily is really great and you'll have a great time. I just probably would encourage you not spend your whole 2 weeks based in the two most expensive and touristy places on Sicily.

I appreciate your comments and think it makes sense not to make our home bases the two most expensive and touristy towns. I'll have to confer with my travel companions how frequently they want to move locations.

Is Palermo a 'must see'? I've heard mixed reviews. Is it better than Catania and if so, why?

Are Noto and Taormina too similar? Is it worth doing both? If not, which would you choose?

Also, we have not booked our flights from Rome to Sicily yet so we could fly in/out of Palermo on either end.

I haven’t been to Noto but I think it is most similar to the other “baroque towns” in the southeast of Modica and Ragusa, rather than Taormina. I have seen Ragusa and one evening on Modica, and I think if you see Ragusa sufficiently it isn’t essential to see the other two. Taormina is different, more of a trendy resort town, architecture more medieval looking, and with an ancient theater which has gorgeous views of Etna and the sea. I strongly recommend seeing it but, as I previously said, I think a week is much too long to stay there. I like Catania a lot, it’s nice and walkable, good restaurants, an excellent WW II museum, it’s an underrated city and a good base, but in terms of a wide variety of attractions such as lovely churches, museums, gardens, and just general ambience for the visitor, I think Palermo is a must see, especially as Monreale is very near and that is amazing, given how much time you have. You don’t want to drive in Palermo though, no need for a car there. With less time such as one week, it’s necessary to decide between east (Taormina, Catania, Siracusa, Etna, Baroque towns), or west (Palermo, Agrigento, and more), and as regions they are equally great, but it looks like you have sufficient time for both.

And just to add, the southeast towns such as Ragusa, Modica and Noto were all leveled by a terrible earthquake in 1693, and were rebuilt in consistent Baroque style on their hills, that is why they are so similar to each other, and their architecture is not the same as Palermo or Taormina, although those certainly have some Baroque buildings also.

I don’t feel Noto is similar to Taormina or Ragusa, for that matter. We loved Palermo and did enjoy Catania. The only city that disappointed us was Taormina.

Last spring, I loved our 5 nights in Palermo and wanted more, my husband loved Catania the most and wanted more than our 3 nights there. We'd been to Palermo and Monreale before on a previous trip. Ortigia was fine for a night or two. Liked Randazzo much more! Modica we did as a day trip from Ragusa Ibla. Noto was one of the towns where we stayed in 2001, but I only remember it as being Baroque and pretty.