Sicily

I have taken the Rick Steves' Sicily tour and would highly recommend it. It will be so much more restful than tackling all the logistics yourself. I felt our time was well spent, organized and included everything I wanted to experience. My guide was terrific.

I've also taken, and loved the RS Sicily tour.
I suggest you have a look at the itinerary for the tour, if only to give you idea of what you might want to do/see if you travel on your own.
https://www.ricksteves.com/tours/italy/sicily
Note that you would not be able to do everything on the tour even if you extended your trip a few days. Public transportation would probably be challenging for some of the sights, and Sicily is bigger than most people realize.

Jessicamar, with all the internet resources available nowadays, researching and planning a trip is very doable, and Sicily actually has good train and bus transportation. Your knowledge of the language is also a big advantage for you. If you are inclined to travel independently go for it. I have gone twice to Sicily and both times used public transportation, although I did use a driver, for specific sites to optimize my time. While I have never travelled on a tour I have on occasion hired tour guides for specific locations. In 2019, a friend and I, ages 66 and 74 at the time, did a 22 day loop around Sicily and all went smoothly. We never felt unsafe. Start by prioritizing the places in Sicily you want to visit. Do you want to limit yourself to the Eastern or Western half of the island? Do you want to visit your ancestral town? Don't pace yourself too fast, choose your must see sites and then decide your route. With only 8-10 days you can't see it all. If you want to see both sides of the island then enter through Catania and exit through Palermo or vice versa. I found the trains easy to use and cheap. I also took busses and again no problem. Like you, I am of Sicilian descent and on my first visit to Sicily I stayed in Palermo as a base and did several daytrips from there, including visiting my grandparents' town and meeting cousins for the first time. On my second trip to Sicily I was retired and had more time so I spent 22 days travelling around the island and still didn't get to see all the places on my wish list. I think you would want to stay at least two nights in each of your chosen bases and with only 8-10 days I don't think you would want more than 3 bases. Take time to explore your base and allow time for a daytrip or two. Sometimes it can be advantageous to hire a private driver for a day's excursions or join a daytrip tour.

Thank you so very much Pat. You have been very helpful. I will definitely consider all your recommendations. Thanks again.

Did you book your train tickets and all accommodations from here?

I booked all B&Bs/ hotels in advance. We stayed in B&Bs, one hotel, and two Air B&Bs. All worked out well. I like to book directly with the business when possible. Train tickets were very cheap, like 5 -10 Euros or less. Train and Bus tickets we just bought at station on our day of travel. Most of the time we just got them from the machine at the station because some of the smaller stations are not manned. Train tickets must be validated in the machine on the platform prior to boarding. Bus tickets we also got on same day. On this last 22 day trip I did book two different drivers in advance. One for a day of siteseeing from Palermo, to Segesta, Erice, and Marsala and one to take us from Agrigento to Piazza Armerina and the Villa Romana del Casale and then onward to Siracusa/ Ortigia. The Palermo driver I found from recommendations on Trip Advisor and the other driver was recommended to me here on this forum. I was happy with both of them.

I agree with Pat. My husband and I spent a total of five weeks in Sicily on two different trips, all by public transportation. We did book most lodging from home ahead of time and transportation tickets as we went along, as Pat suggested. I will point out that traveling with public transportation takes more time. Finding out where the bus stops are and where to buy bus tickets is sometimes challenging. Some of the smaller train stations aren't manned. With only 8-10 days, I think you would see more with a tour. Or you could just do half the island independently this year and the other half independently next year!

I spent 17 or 18 days in Sicily in 2015 (skipping all of Agrigento, Segesta and Selinunte for lack of interest) and always recommend at least two weeks there if you have a car, and extra time if you don't. If you have only 8 or 10 days, you will miss quite a lot of places if you travel independently by train and bus. It's not that you cannot get there but that public transportation is often quite slow (there are no fast trains) and often runs infrequently. A tour would allow you to cover more ground--and spend less time standing at bus stops, but I find tour itineraries don't allow as much time as I'd want in the major cities (Palermo and Siracusa/Ortygia in this case). I know even Rick's tour (10 nights) doesn't go to any of the Baroque towns in the southeast (Ragusa, Noto, Modica and Scicli).

Planning--and going on--an independent trip to Sicily feels a bit like an adventure. I loved it, but I wish I had had more time.

Hi Jessicamar:
I’m also a young senior, and my friend and I are going to Sicily quite soon, all planned independently.
If you would like to know what we have planned, let me know and I will send you information in a private message.

Taking a tour or travel independently is a personal travel choice. My wife and I seldom take a tour since we don’t like being on such a fixed schedule. We prefer independent travel since it affords a greater flexibility on what, where, when, and how long to visit. We also like to pick the hotels and restaurants rather than ones selected for us. For the very reasons we don’t like tours, others do. They don’t want to do the planning and are happy to go where the tour takes them. For some, independent travel is outside their comfort zone.

Planning the Sicily trip was easy. We did have a rental car, but used the local bus to go into Catania and Palermo.