I honestly can't see why one would want special travel insurance to cover PC when travelling to Italy. I have been doing this journey for all of my 11 PC years without any cover. I've lost count of how many times, but it must be circa 50 times. I had a urine infection which took 6 months to clear up, but it didn't stop me travelling. In fact it's easier to get Cranberry juice in the UK, I live in Italy. Things just don't happen that fast with PC. I've travelled to many counties without special cover, including the USA. However my trips are never more than two weeks.
Next May is a long way off, I presume that you don't intend being out of the county for months. The Italian medical system is every bit as good as the British. E111 will cover most things.
Thinking about it I regularly drive to France, Switzerland and Germany without a second thought.
Stu