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. We enjoyed the churches in Noto. For us, it was the views of upper and lower Ragusa that stunned us.

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.

Is Palermo a 'must see'? I've heard mixed reviews. Is it better than Catania and if so, why?
I think most people would say that yes, Palermo is a must-see. Is it "Better"? That's entirely a personal question.
Are Noto and Taormina too similar? Is it worth doing both? If not, which would you choose?
They're not really similar at all. They're both great day trip towns for very different reasons. The real issue is trying to tie your itinerary towns together.
Also, we have not booked our flights from Rome to Sicily yet so we could fly in/out of Palermo on either end.
That makes a lot of sense.

With two weeks, we flew into Palermo (for atleast 4 nights)…then rent a car to see Agrigento and Villa Romano (more if want to) …drop the car in Catania airport and Stay in Catania area at least 5nights in an area convenient to the buses to get up and down the east coast. Do your day trips to Syracusa, Taormina, Mt Etna by bus. Fly out of Catania. Of course this can be done in the opposite direction. As others have said, Sicily is a small island and two weeks gives you plenty of time to get a relaxed overview of the island. The food was exceptional!

The last post makes sense to me - start with a few nights in Palermo and take day trips, drive along northern coast, maybe stop in Cefalu for lunch, then on to to ancestral towns of Oliveri/Falcone. We could get the ferry to the Aeolian islands and spend a night. Then drive to Catania for a few nights and make day trips to Taormina, Noto, etc. from there. Maybe we throw in a couple of nights in Ortigia or Ragusa somehow. It's so hard to decide!

Warning--I'm not sure how often it happens, but we had to stay an extra night in the Aeolian Islands because the seas were rough and we couldn't get back to mainland. So we had to pay for the expensive Taormina hotel that we didn't even stay at, and had to pay an additional night in the Aeolian island (I think it was Lipari that we were on)

Good tip about the Aeolian islands! Thanks for sharing and sorry that happened to you.

Thanks for all of your input. My latest plan is -

Palermo - 4 nights, day trips to Monreale, Segesta, maybe full day tour to Agrigento
Ragusa - 3 nights, day trip to Modica
Ortigia - 2 nights
Catania - 5 nights, day trips to Taormina, Mt Etna, Oliveri/Falcone (for ancestry)

I like it. Although I second Nancy on staying in Randazzo, if you had any interest in splitting the Catania stay.

What is in Randazzo that makes it worth the stay after coming from Ragusa? I think staying at a winery could be fun and of course there is a lot of activity near Mt. Etna, which can also be accessed from Catania. If you had to, would you choose Randazzo over Ortigia which we could do as a day trip from Catania?

I'm trying to keep us to four stops ending in Catania for a few days to accommodate day trips to Taormina, ancestral town (which is closer to Randazzo than Catania but not by much). I think that's as many as stops my group wants to make. During the last week in Sicily, two people in my group need to work remotely so I'm trying to stay in a place where 1) there is sufficient wifi and 2) there is plenty to do on foot and good public transportation if I want to do something solo. I'm not interested in driving.

Is your whole trip using either public transportation or a tour? If so, then your latest plan makes the most sense to me. We were driving and had 4 weeks, not 2. And if you are flying out of Catania, you have to be there the night before anyway.

I don't know how many beds or bedrooms your group needs, but here's the great apartment where we stayed last spring in Catania --- https://www.airbnb.com/rooms/28537611?guests=1&adults=1&s=67&unique_share_id=9b9f82a6-b60d-4fbb-87fd-ebf1d38330bd

Giangilberto from Milan here. Since your live question is Randazzo versus Ortigia and nobody has taken it yet: with your specific constraints, I don't think it's close — keep Ortigia.
Randazzo is a lovely dark-lava town and a great base for a wine-focused trip, but it's car country. The Etna wineries are scattered across the north slope and mostly work by appointment, public transport up there is thin (the little Circumetnea train is charming but slow and infrequent), and reliable wifi in a small-town B&B is a lottery you don't want to play when two people have meetings. If nobody in the group is driving that week, Randazzo loses its main argument.
Ortigia is the opposite: dense, flat, everything on foot. Someone can work from a café in the morning, walk the market, swim in the afternoon. And for your solo outings, Siracusa has proper trains and buses, so you're not stranded without a car.
One thing in Ortigia that most visitors miss, and it's worth planning around: cross the bridge to the mainland and walk about fifteen minutes to the Santuario di Santa Lucia al Sepolcro. Inside there's Caravaggio's Burial of Saint Lucy, painted in 1608 for that exact church — it still hangs above the spot where the saint was buried, and most days there's almost no one in front of it. Check the opening hours before you go, they're limited. Seeing a Caravaggio in the place it was made for, in near silence, is not something Rome or Florence can offer you anymore.
Your final structure looks good to me, and Catania is the right work-week base: flat, walkable, well connected. The only day trip I'd flag is Oliveri/Falcone — that's the one that's genuinely awkward without a car, so consider hiring a driver just for that day, especially since it's the ancestry visit and you don't want it rushed.
One question that changes the math: are your remote workers on US hours? If they start mid-afternoon Italian time, all your mornings are free, and suddenly the day trips get much easier to fit.

We will be driving the majority of the trip. I just wanted good public transportation and plenty to walk to for the end when others may be working. Good points about free mornings for those working in US. Sounds like Ortigia is a 'must' so will plan on that and thanks for the tip on the Caravaggio!