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Three week itinerary for Eastern Sicily October/November

Kportgrl

10+ Posts
Hello everyone. So we have decided to go for it and travel to Sicily this fall. Many thanks to everyone who contributes to this site all the great information about Sicily from experts, travelers, and guides.

Putting together a tentative itinerary for this coming October/November. Our dates are not firm yet partly because of trying to figure out the best time to go, and the least number of flight changes that we will have to make.

We know we can’t fly direct from Canada and will have to stop at least once,.

Many have suggested that it is ideal to fly into one of Catania or Palermo, and fly out through the other. So we are currently looking at that. But we don’t want to do it if it will result in extra cost or Extra flights.

Anyway, here is one scenario which would be landing in Palermo and leaving from Catania. I should add we are looking at staying about 21 days and prefer only 4 bases to stay longer in each place to really get the taste of where were at. We will have a car (except for Palermo), and will certainly consider doing day trips. 45- 75 minutes away.

We have not booked accommodation yet, and I don’t have a moment by moment or even day by day schedule just doing an initial layout .

All of Sicily looks wonderful, but we are going to focus on the eastern side and hopefully will get back to do more on the western half next time.

So if we arrive in Palermo and are able to depart from Catania :

Stop 1 - Palermo 2 nights
Perhaps Private tour the second day to get a taste of the city?
Stop 2 Aeolians 4 or 5 nights
Might split between Lipari and Salina

Stop 3 Taormina 4 nights
Day trips and lots of walking

Stop 4 Siracusa 5 nights

Stop 5 Ragusa 4 or 5

Then overnight near departing city
Broke my rule but figure if Palermo is our arrival city, might as well spend a couple of nights
************
If we arrive in Catania….

Arrive Catania -drive either be driven or drive to Milazzo (drive is 90 minutes)or
Milazzo 1 night?
Stop: #1
4 or 5 Nights Aeolians

Return from Aeolians drive 1:41 to Taormina
Stop#2
4 or 5 Nights Taormina

Drive 1 hour and 20 minutes to Siracusa/ortiga
Stop# 3
5 nights

Drive 1 hour and 16 minutes To spend 5 Nights Ragusa (do noto and modica on day trips)
Stop # 4

Suggestions for sights, accommodation, guides or itinerary tweaks most gratefully appreciated.
 
My main concern would be whether the ferries will be running to the aeolian islands at that time of year and/or are you more at risk of ferries being cancelled. It may be fine, but very much worth checking timetable for the same time last year, and getting an idea of risk of cancellations.

We enjoyed our stay there, even despite the brains of the operation struggling so badly with a sprained ankle, that we ended up getting an x-ray on Lipari. Oddly even that turned out to have positives, from the empathy of a group of elderly gentlemen, to similar compassion from people in the hospital with their own ailments. The hospital staff were great, and although not a tourist experience to seek out ;), we left with a very positive feeling and indeed memories. Away from the tourist trail, Italians can be the most wonderful people.

When we visited, we did the one night in Catania, before heading over to Milazzo, and that worked ok for us, refreshing us with the overnight stay (and a lovely seafood meal in the evening in Catania). You could of course extend this for a couple more nights if Catania appeals, allowing the cities to bookend the trip.

I do like the variety in the islands. Vulcano a raw yet enjoyable experience with its open air mud bath, Lipari and Salina both good options as bases, with plenty in either. Panarea seemed beautiful and relaxing, whilst Stromboli provided the natural fireworks (and a night-time boat excursion is a great way to see this).

I presume that Taormina will be a bit quieter in Oct/Nov (we never went there). Whether it feels like it's the 'off-season' at that time of year I don't know.

Plenty of other options available if closer inspection of time of year effect puts you off Taormina and Aeolian islands, and it should make it a nice temperature for exploring. e.g. rather than east or west, you could do an east to west trip (mostly) along the south coast.
 
Thanks Ian. I did not realize it would be possible to check last year’s schedule. I will have a look at it. We are quite flexible in our timing so we can certainly go earlier in the month if it looks like it will be a safer bet, which I imagine it will.
 
After 33 years of Italy travel, we're finally making our first trip to Sicily--so I can't speak from experience yet. Our trip will be from the tail end of April through mid-May, and we went round and round about making the trip relaxing without too many relocations or too much driving for day trips. In the end, we finally decided to fly into Palermo, but we decided to stay 5 nights in Trapani instead of Palermo, with day trips planned to Erice, Segesta, the Zingaro nature preserve, and Favignana. After that, a couple of nights in Cefalu, then the balance of the trip in Ortigia and Taormina before flying out of Catania. We'll probably get to Noto, but decided to save Modica and Ragusa for the next trip. Can't possibly do everything--or at least not Slow Travel style--in a single trip.

Your trip sounds lovely, although I might plan for early October rather than late October or November to minimize weather cancellations for the Aeolian islands. You could probably minimize your car rental by reshuffling the order of the destinations: your car will probably be parked the entire time in Siracusa (especially if you stay in Ortigia), as well as your time in the Aeolian islands, and the car is probably unnecessary in Taormina as well. This is backtracking a bit, but you might want to consider Palermo to Ragusa, then drop off the car in Catania. After the Aeolian islands, you could probably do fine by public transportation in both Taormina and Siracusa/Ortigia.
 
After 33 years of Italy travel, we're finally making our first trip to Sicily--so I can't speak from experience yet. Our trip will be from the tail end of April through mid-May, and we went round and round about making the trip relaxing without too many relocations or too much driving for day trips. In the end, we finally decided to fly into Palermo, but we decided to stay 5 nights in Trapani instead of Palermo, with day trips planned to Erice, Segesta, the Zingaro nature preserve, and Favignana. After that, a couple of nights in Cefalu, then the balance of the trip in Ortigia and Taormina before flying out of Catania. We'll probably get to Noto, but decided to save Modica and Ragusa for the next trip. Can't possibly do everything--or at least not Slow Travel style--in a single trip.

Your trip sounds lovely, although I might plan for early October rather than late October or November to minimize weather cancellations for the Aeolian islands. You could probably minimize your car rental by reshuffling the order of the destinations: your car will probably be parked the entire time in Siracusa (especially if you stay in Ortigia), as well as your time in the Aeolian islands, and the car is probably unnecessary in Taormina as well. This is backtracking a bit, but you might want to consider Palermo to Ragusa, then drop off the car in Catania. After the Aeolian islands, you could probably do fine by public transportation in both Taormina and Siracusa/Ortigia.
Thanks Lisa. I’m really second guessing my desire to side trip to the Aeolians. Obviously we can’t fit everything in but I’m thinking if we can’t get there, we’d have to scramble, which is not our preferred thing to do when we’re in a country where we don’t speak the language. ‍♀️ i honestly don’t know if we’ll ever go back; two flights and not cheap but at the same time, we don’t want to rush. I’ll have to figure it out.
 
we loved Trapani! but 5 nights may be a little too long. we stayed in Castellammare del Golfo for a couple of nights (right upon arrival) and it was a very convenient base for a hike in Zingaro, plus it's got a very picturesque and not crazy-crowded historic area.
we used Azzurra Cusenza as a tour guide for Segesta, Erice, and Mozia and found her to be engaging, highly knowledgeable and a lot of fun as well!
Cefalu was our least favorite place in Sicily, although we did love the Cathedral visit. we ended up only staying one night instead of two.........
 
we loved Trapani! but 5 nights may be a little too long. we stayed in Castellammare del Golfo for a couple of nights (right upon arrival) and it was a very convenient base for a hike in Zingaro, plus it's got a very picturesque and not crazy-crowded historic area.
we used Azzurra Cusenza as a tour guide for Segesta, Erice, and Mozia and found her to be engaging, highly knowledgeable and a lot of fun as well!
Cefalu was our least favorite place in Sicily, although we did love the Cathedral visit. we ended up only staying one night instead of two.........
Good to know. Many of our plans involve outdoor activity, like biking in Favignana and hiking Zingaro. And we may backtrack a bit and spend some time in Palermo.
 

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