For me, it was the red herring about 'Syracuse', although I knew about the ancient city. So after 23 obvious cities, I guessed Sausalito, which sounds the most Italian. It was possibly the same for others.
I still picked it because I thought it was the Italian one so I understand why you would leave it but it is still slightly unclear as you dont define city. Perhaps if you say 'most populous city with this name' if that is the case for these
That's a good suggestion. In this case, anyone who has heard of that village will have heard of the other Italian cities too. And the best sudden strategy to pick off the most likely options first. Also, someone who knows the village will surely think "This has been made by an English speaker, and they will be referring to the Libyan city".
That Tripoli in Italy is no municipality though (hamlet of the municipality San Giorgio Bigarello). One could specify that just municipalities are valid.
And it kept working!
The last two sounded more spanish though, so it was sausolito that got me.
Not a city, then, so it's still fine to leave it there.