I have racked my brain to find the best solution. I wonder if anyone has any other ideas.
I have 6 weeks in Italy, Greece and Turkey. Starting in Milan, somehow hitting Palermo and Puglia, and flying back from Athens. Got a rail pass.
My original plan was to proceed down from Milan to Puglia over time, then take a ferry to Corfu, and train to Athens (before we added Turkey). Also, I wanted to add Palermo, since I have been to eastern Sicily and loved it but never the main city and that area.
A. Its possible to take train down to the tip of the boot and ferry over to Sicily, roam around, then come back that way, and train over to Bari/Brindisi/Monopoli. But these are slow trains for the most part. Then get to Greece and try to take their trains up around to Istanbul. This is also slow and time consuming. A year ago, I took the train from Paestum to Taormina and it was essentially 8-9 hours. Its only 3 hours to get to Region Calabria, but despite the ferry taking 30 minutes, I think it took a full 2 hours of screwing around with putting the train on the ferry, then taking it off the other side.
B. I can just fly from Milan down to Palermo train over to Puglia stopping in Amalfi coast, then fly from Bari to Istanbul, then fly or ferry back to Greece. So two flights that cover a long distance. They are not too expensive. Bari seems to be the air hub for hat region. But the Bari - Istanbul flight is only a few days a week, and sometimes arriving at night, and price varies a lot and is super expensive the most ideal day ($135-$250).
C. Another idea is to take high speed train from Milan to Bologna to Ancona to Bari - make Bari a base and go up and down the coast, then go west to Naples/Salerno/Amalfi, down to the tip of the boot, over to Sicily and to Palermo. Then just make one flight from Palermo to Istanbul. Only problem with that is there is no non-stop flight at all, so you end up flying to Bucharest, Romania or elsewhere, and taking two flights and spending the whole day.
D. there are also a fair number of non-stop flights from Naples to Istanbul. A little more expensive ($180 ish). That works well for hitting Puglia then Naples. But what about Sicily? Overnight ferry to Palermo, and back?