That's exactly how I got to be in the region. I'm fairly certain that last night it was asking if I wanted to enter 'Drangheim', not 'Drangheim City', but I rebooted today, and it now reads 'Drangheim City' and it doesn't crash!?! IS there some associated bug with the box asking about 'Drangheim' that I got around by rebooting?As far as the prison is concerned, the save I was using did not have me as having entered the prison.
I save often and roll over old saves as I go, but use multiple save slots.
All *seems* well now. Thanks for taking some time to ponder this one.
Happy Gaming