Two retired teachers heading to Sicily end of October/beginning of November and then finishing the trip in Siena, Italy Nov. 9-14. We have been to Siena but not to Sicily. Hotel is booked in Siena but trying to plan a new adventure to Sicily. Trying to determine the most efficient/cheapest way of traveling to Sicily from the US with the least headaches. Should we consider CTA or PMO? Best European airport for transfer to Sicily? Since we are retired, we have flexibility. Not sure where we should spend a week in Sicily but want to take advantage of public transportation. Focus on just one city? Heard great things about Ortiga......is it worthy as a destination? What is the best way to get to Siena from Sicily?
Check www.Skyscanner.com for airfares to the various airports.
For Siena, check airfares into the Pisa and Florence airports.
Which airport and which European hub depends on where you are starting from --- we usually fly Delta to Amsterdam and then Rome to wherever. I use Google Flights to figure it out, then buy directly from the airline. On our most recent trip to Sicily we flew to Rome and then had separate ITA Airways tickets to Palermo --- not ideal, but it worked out fine. I believe that Catania is the bigger airport with more flights, but roundtrip FCO–PMO suited our plans better. So, yeah, it depends.
Where to go for a week in Sicily also depends. For one example, I am a huge fan of Palermo because of all the art, architecture, and mosaics to see there, but my husband was a fan of the grittier, less touristed Catania and its better food market. We loved the food everywhere we went. You can read my whole trip report here: https://community.ricksteves.com/travel-forum/italy/sicily-spring-2025.
Sicily to Siena could be fly to Rome and then either a Flixbus to Siena or a train to Florence and then a bus or train to Siena.
I am really glad that you chose October/November --- it's one of the very best times to go to Italy!