Any luck extending a hotel voucher beyond Dec 2021?

The obvious-did you ask them?

I think you'll have more leverage if you ask closer to the expiration date as opposed to now. When given a "gift" of sorts, I would hold back asking for a "better gift" until more time has passed and I have an authentic rationale for why I need it. Besides, you may not want to extend it for 1-2 extra years since, who knows, the hotel may not survive that long. Personally, I would revisit this closer to the expiration date. I wonder if there is an Italian law that states (something like) they'd have to refund the money if voucher is not used within a year.

When I was getting a voucher for one non-refundable night, I found that it helped to let them know that I was from a non-EU country. Realizing that I would be unable to travel as soon as an EU traveler might be able to, seemed to help. We received a 3 year voucher instead of a 1 year voucher. I do think this hotel (an RS post-tour hotel) was trying to be very generous, and might have done this anyway.

If they realize you are not from an EU country (which may or may not be obvious from your email address and communications with them) it might increase flexibility. Even if it is apparent, it might at least give you another opening to politely request a longer timeframe.

Ruth, I think the only "way" is to ask the hotel itself. Properties are not all going to respond the same so even if someone did manage to get their voucher extended beyond next year, that doesn't mean your hotel will be willing or able do that.

When it comes down to it, that they offered a voucher at all on a non-refundable booking AND that it's good for 18 months, is very generous, given their (I'm sure) severely reduced circumstances. :O)

Can it be transferred? You could ask that too. It might help if you have someone interested in using it in a specific timeframe....though that might be a bit harder to organize....unless word gets out here and someone offers to buy it off you.
Otherwise, write a nice review for them offeringbuou a voucher on a nonrefundable booking and take your knocks. Lesson learned.

Yes, I am very pleasantly surprised that they replied to my email within a matter of hours and that they offered a voucher despite the booking being non-refundable. I would definitely try to stay with them again if/when we are ever able to return to Rome. Really good customer service, especially as I’m sure they are also struggling. Hotel Damaso, btw.

Hotel Damaso looks lovely, Ruth, and in such a convenient location to so many interesting things to see. Crossing fingers that you get to hang your hat there sooner rather than later!

Umm, to be honest, I’d put this on the furthest back burner for a year. There’s no way you can ask the hotel now without coming off looking like the villain.

The Italian law about this emergency says that the seller (hotel, museum, tour operator...) must refund a booking or a ticket. The refund can be done giving back cash or giving a voucher: the choice is done by the seller, so the most decided to give a voucher. The voucher must be valid 1 year from the date of issuing.
In your case you have received a voucher more or less valid 18 months, so they comply the legal requirement. Of course you can ask for a longer expiration term: the hotel can do it.
The law says nothing on selling of vouchers, so resell it depends by the kind of voucher. If is a simple part number not related to a name, should be easy resell it.

Update: I received the cancellation notice and voucher by email this morning. I am not going to ask for an extension. The voucher is both fully transferable and can be broken up for multiple stays. Honestly, even though we might not be able to use it, I feel they are being as generous and flexible as possible and have decided not to ask for more. Thanks, everyone!