NYC to Sicily (Palermo)

I've done the separate flights changing in Rome to get to Palermo trip.
The basic advice is to leave a minimum of 4 hours between because things happen, including the possibility that your NYC to Rome flight has a delay. You won't be compensated if you miss the second flight if it's not on the same ticket.

I flew from Catania to Rome at the end, stayed one night, and flew home the next day.

If you have the time, we planned on two nights in Rome on the way to Sicily, it allowed us to adjust, then caught a cheap Ryanair flight to Palermo. On the way back, we actually flew Catania to Naples, spending a few nights in that area, then train to Rome, and another couple nights.

I might be tempted to leave a 4 hour buffer at the beginning and catch a flight to Palermo right away, in worst case, might have to buy another ticker, but it would not be much.

On the way back though, I would not try to link up an independent Catania-Rome flight to get on a Rome-US flight. I would at least be in Rome the night before. Your transatlantic flight is just too big a risk, and expensive to replace.

We do not have time for stays in Rome on the way in or the way out without extending our vacation. Is it worth it to fly out of Catania on an evening flight the day before our flight from Rome to NYC just to stay at a hotel near the airport to be sure to not have an issue connecting? this would mean paying for a hotel in Catania as we have plans the final day so cannot check out early and then paying for another hotel for the same day in Rome just to be sure we don't have an issue connecting?

I wish we had more days, would love to be able to do a month in Italy!!

Almost every hotel will hold your bags after check out, so unless you feel you need the rooms all day you don’t need that last night hotel in Catania

In March last year I flew JFK to Palermo then Catania to JFK via Rome on Delta. The Rome-Palermo and Catania-Rome was actually on ITA but it was all purchased on one ticket via Delta. Are you sure they are no longer offering this option. I did not have to deal with my checked luggage until I reached Palermo. I had no problems with the flights. I did have to take the first departure out of Catania, 6am, to make the connection in Rome to JFK in order to not have to spend an additional night in Rome but to me it was worth it to get home the same day (I actually flew to/from Cleveland to JFK on the same ticket). The airport in Catania was pretty empty and easy to navigate that early in the morning. I loved Sicily.

We took that tour this past April. We live in Boston and flew into Palermo and out of Catania on Lufthansa - transferring in Munich. We flew premium economy which only applies to the transatlantic portion of the flight. If you are going to travel with that much luggage, which I would not recommend, I think you're going to want to check your luggage through. Are the 4 senior relatives able to carry their own checked bag, carry on and personal item to/from the bus at every hotel? The bus does not necessarily park in front of the hotel. I can think of at least 3 hotels on that trip where we had to walk at least a few blocks from the bus to the hotel.

I am certain that as of right now at some point in April Delta no longer offers flight to Palermo with a connection in Rome. If you go on the delta site you can schedule the JFK to Palermo with a stop in Rome in March but if you try to book thereafter it’s no longer an option. However at that point you can fly directly to Catania.

We are on a private tour and have all the details once we are in Sicily worked out so that the seniors are taken care of completely. There is no concern about luggage after we navigate the airport situation. But thank you for the advice. I went to great lengths to be sure they would not have to struggle with any of that.

Are the regional ITA flights reliable? I am a little worried about arriving late from Catania and missing the Rome to NYC part as someone mentioned. Even if we leave a 3-4 hour window.

Flights to Sicily from FCO are usually on smaller jets (think 737 size) that are parked out on the tarmac. So you need to arrive in Rome, get your bags, go thru customs, go to the ITA gate (note that boarding can close 30 minutes before the flight), take the bus to the plane. With 3-4 hours it may work out, perhaps usually it does, but not always. If it were my trip I'd arrive in Rome and spend the nite before travelling on a second ticket to Sicily.

We flew RT in and out of Rome, and did RyanAir to Palermo and back (we were supposed to fly back out of Catania, but ended up flying out of Palermo due to a COVID interruption). Keep in mind also that the regional flights (ITA, RyanAir, EasyJet) can be delayed or cancelled. We waited over 6 hours in Palermo due to a airport workers strike that grounded planes for an afternoon. So on the return to Rome from Catania, I would also recommend a hotel near the airport in Rome for the night before your flight (we liked Hotel Tiber in Fiumicino, they have a shuttle, but there is also a Hilton hotel literally connected to FCO that might be a good choice)

ITA sucks.
We paid to fly business class from/to FCO-CAT.
Horrible. Water and stale crackers. Nothing else. No booze. No other food.
$100/leg/person. Total ripoff.

Considering the composition of your group, the last thing I would want to do is a self-managed connection at FCO on separate tickets. A through booking on ITA is probably your best best, and Lufthansa also appears to offer good options.

Delta looks a bit odd at the moment if you compare the same search result between the Delta website and Expedia. It may be related to the anticipated departure of ITA from SkyTeam. And perhaps a bit early to be booking tix for next October.