travel insurance for Italy

We typically travel independently, so I don't get cancellation insurance since we are not purchasing a travel package. My business class airfare is purchased with frequent flyer miles, so I purchase the inexpensive and limited Allianz insurance policy that is offered on the AA website at time of ticket purchase. I only stay at hotels that have generous cancellation policies and where I pay in-full at the hotel when I check in. I once canceled 3 hotel reservations one week before departure due to transportation strikes in France, and we were not out a dime.
When we have taken RS tours that require payment before the trip begins, we purchased travel insurance from Nationwide. Before one RS tour, our flight was diverted and we had to land at PHL and spend the night. For the trip interruption, Allianz paid by the end of the week to cover the cost of the hotel, and Nationwide paid within 2 weeks to cover the cost of having to make a change in our airline ticket for a flight within the EU.

We have an annual medical policy with Geo-Blu, and an annual policy for medical evacuation with Medjet Assist. Fortunately we never had to file a claim with either.

Never heard of Faye

You can compare plans at
insuremytrip.com
squaremouth.com

Lots of discussions here on forum
https://search.ricksteves.com/?button=&date_range=2y&filter=Travel+Forum&query=Trip+insurance+

Allianz has been recommended many times on the forum. I have bought trip only and annual policies with varied coverage. Fortunately I have never filed a claim with them.
For med evac I have bought annual MedJet policies. Again, no claims.

I vaguely remember someone posting about Faye insurance maybe a year ago. Try the search feature to see if you can find it.

I've purchased Allianz policies for multiple trips, and unfortunately had to use if a few months ago due to a winter storm delaying us for days on our return home.

I have to say that the claim process was fairly straightforward and they paid the claim quickly. They initially asked for receipts for hotels, taxis, meals, etc... I was only able to provide them with the credit card statement as getting an actual receipt from the hotels after the fact was way more difficult than it should ever be. After backtracking to try and get the receipts, I received confirmation that the claim was now paid.

So my lesson learned was if you get delayed or feel you're in a situation where a claim might be necessary- GET RECEIPTS FOR EVERYTHING.

Never heard of Faye. Keep in mind most companies have a pre-existing conditions rule where they won't pay and also most, even the ones that call themselves primary insurance, require you to first pay the bills and then apply for reimbursement. So you'll want to look into that. We've used GeoBlue (now called Blue Cross Blue Shield Global Solutions) since they waive pre-existing conditions and as a part of Blue Cross have an overseas network of doctors and hospitals where they will pay directly rather than just reimburse you.

For me, insurance is to pay for large unexpected expenses. I don't cover my trip costs because I'm already able to pay for the trip. Sure would suck to lose that money but it wouldn't be catastrophic. A $50K medical bill, on the other hand, would be trouble. On the other hand if I was booking a once-in-a-lifetime trip maybe I'd consider cancellation insurance but it adds 5% or more to the trip cost.

I suggest you call tripinsurancestore.com and talk it thru with them since Steve is pretty knowledgeable about travel insurance (you can look for other reviews here on the forum). I buy my GeoBlue policies from them since it doesn't cost any more and they're helpful to talk to.

A friend of a friend had a bad bicycle accident in Italy, everything medical was covered by Geo-Blu (also part of Allianz). Have a look at your airplane ticket, it's very likely IF you're using a major US carrier, you can cancel & store the credit with the airline, good for up to a year.

We have exactly what AlohaLover describes -

We have an annual medical policy with Geo-Blu, and an annual policy
for medical evacuation with Medjet Assist. Fortunately we never had to
file a claim with either.

We've used TravelGuard for a number of tours and cruises. Had to file a claim a couple of times. Had to provide documentation, but nothing unreasonable. Claims paid within a couple of weeks.

We also have MedJet Assist for evacuation, but, thankfully, have never had to use it.