We are planning to go to Sicily in mid- to late-September for about 15 days. We can't fly directly there so we most likely will fly in and out of Rome. We're trying to decide on an itinerary. We're looking at spending about 4 days in Rome and then making our way to Sicily (flying?). But we're also considering leaving Rome out (ie just connecting from there straight to Sicily) and saving Rome for another trip (that would include more in that area rather than travelling down south). So we'll either have 10-11 days in Sicily, or 14-15 days there. We know that Sicily has all the things we are looking for - history (archeological sites, museums), great food, immersing ourselves and exploring cities and interesting places, some beach time, maybe wineries and/or agriturismos. We're not sure how many bases to have so that we have a good mix of seeing a lot, but also not just touching the surface. We love doing some off-the-beaten path type things.

When we traveled in Sicily I had the impression that Caltagirone and Selinunte had fewer visitors ;than other sites:

https://flic.kr/p/8hRBRC https://flic.kr/p/8hN1UT
It might also be true of places like Randazzo:

https://flic.kr/p/8hN9nK

Thanks. Great pictures.

while we were planning our first trip to Sicily three years ago, I watched a few you tube videos to get a feel for the island and get visuals for places I had only read about. Sicily Unpacked was very good (although we found both travelers/guides kind of annoying) and so were several of the Rick Steves videos. that helped crystallize for us what were the most important things to build into our itinerary.

It also helps to have a solid understanding of the kind of traveler you are. for example, my husband and I like to get an early start to the day and prefer to stay over the night before a visit to major sites -- Valley of the Temples, Villa Romana del Casale, even though it means moving around a bit. Some travelers prefer to stay in one place for several days/nights and do day trips to visit places, and not have to re-pack and change locations, even if it means an hour or so of driving each way.

Thanks @adlmillr. We are mix of both types of travelers. We don't mind quick stays and moving around for some of the time, but also like to spend a few days in some places to take it more slowly and explore. I'm starting to think we should save Rome for another time and spend all our time on Sicily. Even with the full 14-15 days, I think we'll need to hone in on specific areas of Sicily.

We did a week in Sicily and spent three days in Palermo, one overnight in Piazza Armerina (visited Villa Romano del Casale) and visited Agrigento on our way to
Siracusa where we spent three nights. We enjoyed all of these places and would have loved to have more time to visit other locations. We rented a car when we left Palermo and dropped it off in Siracusa. Enjoy your planning!

@JSG exactly. We're returning to Sicily in October, and will spend 15 nights, then fly to Rome for 4 nights before returning home. On this trip, we'll be visiting Western Sicily, which we didn't get to see on our first visit, then Cefalu for a couple of nights and a return to Taormina and Ortigia, with a few nights in the Vittoria and Ragusa area, before departing from Catania. We'll have a car the entire trip, which is the most flexible and economical option for us.

Thanks!

It seems like there is a lot to do in Western Sicily. Maybe base in Trapani and day trips from there? I've put together two potential itineraries, one that is a bit slower and focuses on the west and one that includes more on the entire island.

Plan A- Palermo 2-3 days with 1 base
- Trapani and area 4-6 days (1 base, or multiple bases?
- Agrigento and area 1 day (or possibly a day trip)
- Stay at a winery/agriturismo on the way from Agrigento to Cefau for 1 - 2 nights, or that Madonie hill towns?
- Cefalu for 2 nights

Plan B

- Palermo 2-4 – 1 base
- Trapani and area – 3-4 (1 base)
- Modica and area 1 (stay overnight or stop on way to Ortigia?)
- Ortigia 2-3
- Catania 1-2
- Visit the town of Enna on way up to Cefalu (worth an overnight?).
- Cefalu 1-2

**neither of these plans include Taormina or visiting Mount Etna, or Aeolian Islands, all of which I would also like to consider

Plan C
Fewer bases, with more day trips. Eg/ stay in Palermo, Trapani, and Ortigia or Catania.

Here's our itinerary:
Castellammare del Golfo, 2 nights: we'll head here right from the airport and try to relax and recover from jet lag on first day/night, then spend the next day hiking in the Zingaro Reserve. on the morning we leave, we'll drive to Segesta bright and early to meet our guide when the site opens, and from there follow her to Erice for visit and lunch
Trapani, 2 nights: we'll use Trapani as a base to visit Mozia and the salt flats
Cefalu, 2 nights: climb La Rocca when we arrive, walking tour of Cefalu next morning
Taormina, 2 nights: leisurely drive on transition day, possible detour to Randazzo for lunch, to sample local products and wines
Vittoria, 2 nights: stay at Baglio Occhipinti, relax, visit Marina de Ragusa and beaches, possibly arrange some wine tastings
Ragusa Ibla, 2 nights: explore both areas of Ragusa, Ibla an Supeiore, possible visit to Modica; on transition day, local slow food tour with Smile and Food
Ortigia, 3 nights: just because we love it! see a puppet show, visit archeological museum, drive to Vendicari Reserve
drop off car at CTA and flight to Rome

It is a lot of moving around, but this allows us to mix more modest accommodations with some nicer places, and be able to splash out on some nicer meals. We travel light and don't take up a lot of space with our stuff, and we're early risers so getting out early is never a problem for us. On our first trip we spent time in Palermo, did a day trip to the Etna area for food and wine tour, visited Agrigento and Villa Romana del Casale, so we don't have as many "must see" sites on our list for this trip.

Thanks adlmllr. This is helpful. I think we've settled on a loose plan so far that focuses on the east side, but also Palermo. I don't imagine we'll be back again (there are no direct flights for us to the island) so we want to check off as much as we can but also take time to enjoy some spots. I think our main areas of focus will be Palermo and Ortigia. With potential day trips from each, and maybe split up some to stay at other places nearby (eg/ maybe Ragusa Ibla or Modica, maybe winery near Etna, maybe Cefalu, etc.). But there's so much we want to see in do in Palermo and Ortigia alone. I'm very excited about the Vendicar Reserve as well. The big things I think we'll be sacrificing are the Trapani area (looks amazing), Agrigento, and Taormina. We might try to go on a tour of the Aolian islands, but we might have to skip that one too. We are hoping to fly in to Palermo and out of Catania and we're going to investigate whether we need to rent a car or can do most of it via public transit, tours, and taxis.

I think we have settled on a general itinerary (exact number of days in each location yet to be determined). Flying in to Palermo and out of Catania.

Palermo - 3-4
Agrigento - 1-2
Ortigia - 5-6
Taormina - 2-3

We will do day trips from these places to Cefalu, Baroque towns, Etna, beaches, etc.

Will the water be warm/swimmable in to the first week of October?

It sounds like you have a great plan. Have a wonderful time!

Looks like a great itinerary! Now the fun begins, filling in the blanks of what you'll do/see each day.

And just when I thought it was settled, we discovered that a better flight option for us is likely a direct flight to Lamezia in Calabria. So now we are thinking of doing that rather than flying in and out of Sicily. In which case we will cut out some of our Sicily itinerary and do some exploring in Catania. It makes sense to cut out Palermo and focus on the east side of the island. We still really want to go to Ortigia, but maybe we'd also visit Catania in place of Palermo. And although it doesn't make sense logistically, we still really want to visit the Valley of Temples so I think we'll still try to fit that in. Perhaps we will substitute a place in Calabria (Tropea?) in place of Taormina. I was wondering if anyone has other suggestions? And since we'll pass through Messina now, is it worth staying there for a bit? Thanks.