Night Train from Freiburg to Sicily?

This is a trip that will take a while, unless you have a Tardis. A good start is as always the Man in Seat 61: https://www.seat61.com/Italy.htm#london-to-sicily-by-train

Personally I would stop somewhere along the way to break up the journey.

I took a night train from Rome to Palermo. That experience cured me forever of the insane notion that trying to sleep on a train is a clever substitute for a night in a hotel bed that's not moving in a quiet, dark room.

The train was utterly miserable. Un-ending, skull-splitting noise. Constant motion. Bright lights. Not 10 seconds of actual sleep. This was in what I would otherwise describe as nearly optimal conditions: a private compartment, just me and my spouse, comfy bedding, reasonable temperature and fresh air. It was clean enough (not spotless, but not cringe-worthy). The plumbing worked. But none of that mattered at all after a few hours of trying to nod off. The extreme noise, motion, and light = 100% fully awake every minute of that long journey.

The next 3 days were also miserable, as I sleepwalked though ruins, cafes and scenery.

Nights trains - I've tried them several times. I'm done with that. Life (and vacations) are too short to inflict that kind of torture on myself. YMMV.

Check the train schedule here:
https://www.bahn.com/en
The best options seems to be a departure from Freiburg at 10:15am with arrival at Siracusa at 9:01am the next day.
Only two changes, at Milano Porta Garibaldi and Roma Termini. The issue is that you need to transfer also from Milano Porta Garibaldi (where you arrive) to Milano Centrale (where you take the train to Rome). The Rome-Siracusa portion is on a night train.

I have never been able to sleep on trains, so that would not be my cup of tea. Trains are nice, but the constant jerking around and noise is not sleep conducing to me.

Have you checked EasyJet from BSL to Catania? BSL Euro-airport is only 45 min from Freiburg, on the French side of the border. EasyJet is a budget airline and has direct flights from there to Catania.

I'd take a train to Milan and then fly to Sicily.

Second best, a day-time, high speed train from Milan to either Naples or Salerno. Then a ferry to Sicily.

Sorry, but a "night train that originates in Milan" is not a night train if you have to "change in Naples at midnight". I assume (hope actually) you are taking a direct 4 hours and 33 high-speed train from Milan to Naples and only in Naples you are taking the night train #1975.

Please don't do this. I, too, have taken that train, back in 2015. I, too, didn't sleep for even one second. It was far more miserable than sitting up in a coach-class seat on an overnight flight. I was in a couchette; the carriage jerked side to side constantly. My arrival day in Sicily was a total loss. The train was also delayed for multiple hours at the crossing point over to Sicily, but that seemed to be related to construction work on the line, which I assume has long since ended. I don't remember a significant issue with the air conditioning.

Have you checked EasyJet from BSL to Catania? BSL Euro-airport is only 45 min from Freiburg, on the French side of the border. EasyJet is a budget airline and has direct flights from there to Catania.

I am with Roberto on this idea.

Looks like the day of the week determines the departure time, but with your 'loose itinerary', choosing a noonish departure should be fairly easy, and get you to Siracusa around 4ish, to make check in feasible at your lodging.

and the late afternoon flights would get us into Siracusa too late for your standard B&B arrival

What about just taking a late flight and booking one night at a hotel near the Catania airport? Head to Siracusa in the morning.

I hate night trains (took many in my youth to save money), so to me 24 hours on a train sounds way worse than getting up at 5am to take an early morning flight.

I just want to add that the Basel-Mulhouse airport is serviced by a very reliable Flixbus connection from Freiburg itself, that tends to line up quite well with departure times from the airport, so getting to and from Freiburg is straightforward. I have not taken it since before covid, but I think it is maybe a 45-55 minute bus ride from the Hauptbahnhof of Freiburg directly to the terminal doors at the airport.

Thanks everyone for your honest feedback. At this point I am not going the Milan or Rome to Sicily night train route. Instead I am looking at breaking up and taking day trains. The flights still just don't make sense from Freiburg. May fly from Milan as I have never been outside the train station. Or may fly from Rome where they seem to have oodles of cheap flights all times of the day. A day or two on the train seems like a nice respite actually. I am going to post about a nice, easy village to stay a night along the route separately. Also, a hotel option near train station in Rome. Funny enough on my first trip abroad almost 30 years ago I stayed in a RS budget recommend in Rome where the conductors slept during the day and tourists slept at night. Looking for something a little more "standard" this time:)