Quarantee requirements

I did purchase "cancel for ANY reason" insurance but I'm not sure it's being honored

The only way to get the answer for that is to contact the carrier.

God is the only one who knows what protocols/restrictions will be in place in October, but I do not think he will spill the beans.

What quarantine might be in force on return to the US could depend on which state you are going to. With the start and stops of 'reopening', in just the last 3 weeks, I doubt any accurate forecast for October is possible.

"All Rick Steves' Europe tours are cancelled through September 20, 2020. We are not currently accepting new bookings or final payments for any tours in 2020, as we wait to see how the fall season unfolds." from the website. Tours are not individual travel, but RS has great contacts everywhere in Europe.

As for flights/refunds/quarantines/etc in October.... Really all anyone can do is wait until the month before the trip and see what is going on. 30 days before our scheduled trip this summer it took one visit to the website and one short phone call to get our flight refunds credited. Insurance won't really want to pay until they have too - again not until near the time of the trip.

Good luck.

1. Right: at the moment for US leisure tourists the travel is not allowed. For Italy this restriction is valid until the 1st of July, but is possible it will be kept even later. Will depend by the news. The Government is writing a new decree to confirm of stop restrictions every two weeks, more or less. At the moment the situation is quite normal in Italy, but is impossible foretell next decision. Maybe in July travels will be possible, maybe won't be possible for the whole 2020.
2. Right. At the moment this rule is still present, but is strictly connected to the point 1. Must be respected to travellers from outside Schengen area then must travel to Italy.

• Voucher: the law says that a refund for a cancellation due to COVID is mandatory. The company (museum, travel agency, tour operator, hotel...) who issues the refund is free to decide to give back cash or a voucher. The voucher must be valid at least one year after the issuing.

These are good questions.

What I'd like to know is can we travel US to Italy if we are delighted to quarantine in a remote place (that we own) for 2 weeks.

David,
At the moment they are restricting travel from outside the EU only to returning residents, persons traveling for emergency reasons, essential work travel. Even those traveling on the above circumstances are still required to quarantine for 14 days, and are prohibited from using mass transit during that period.
You would need to prove that your travel is urgent and undeferrable.

Absolutely unofficial info -- according to my German-citizen husband's friend in Germany, he would be allowed into Germany from the U.S. with quarantine of unspecified period -- and I as spouse could tag along. We're not making plans right now, though.