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@Chris Self Hi , how are you? Since your girlfriend is Italian you should be able to apply for the residence permit on the cohabitation basis "convivenza di fatto". I posted a topic on this subject and someone who is in the same situation as you said he did it in Milan. I think you have to go to the comune you are in to register ,then to the questura after 8 days of being in Italy. For more info you can make an appointment with "cinformi in Milan. I hope this helps.

Ciao!

@sadiedez.729 I'm very well thank you! Thanks so much for the response it's really useful. I didn't know about the convivenza di fatto, sounds like it could simplify things! Would it means then that you would only need that to work legally in Milan and wouldn't need a visa at all? Also could you give me a link to the topic you posted so I can have a read?

Thanks so much!

Chris

Youll be working 'in the UK' and presumably will be taxed in the UK so your problem is not working in Italy, but being allowed to stay over 90 days.

Your only option is the convivenza di fatto permesso di soggiorno,  but the granting of it is discretionary.   If you opted for a civil union you could get a permesso for 5 years.

@Chris Self hi and sorry for the late response.

"To apply to this convivenza the NON EU person must have already a previous perms di soggorgio otherwise she/he can't apply..

The point is, do you guys have already the declaration of coppia di fatto from the comune in which you have your residency? if yes you just need a few other documents, very simple.. no lawyer at all

@Chris Self Ciao Chris it's complicated! My husband has very recently had to move back to the U.K. to keep his job 😓. He was working for a U.K. Como many but remotely from Italy. Basically forget about the nomad visa in Italy, as far as we've been told, it's been scrapped by the current government. My husband has dual citizenship Italian British and has no visa issues but it all boiled down to fiscal residency and in our case the company's willingness to post him abroad.

The 183 days rule applies in the U.K. as you might know to establish fiscal residency. if you become resident in Italy (after 90 days you have to register with your local anagrafe and you become a resident) you have to pay tax and social contributions. A U.K. company might not be able to post you here, as the case with my husband. One possibility is for the U.K. employer to use a global employment company such as Oyster HR to mention one.. The other option is to put you on a contract for services and in that case you would be self employed and should be able to apply for the relevant visa. This is as much as we've understood but best to double check facts. There are very good Facebook groups like British expats in Tuscany and Maremma or even better U.K. citizen's rights in Italy - Beyond Brexit who are way more  knowledgeable than me! 

Good luck! 

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@Chris Self Ciao Chris it's complicated! My husband has very recently had to move back to the U.K. to keep his job 😓. He was working for a U.K. company but remotely from Italy. Basically forget about the nomad visa in Italy, as far as we've been told it's been scrapped by the current government. My husband has dual citizenship Italian British and has no visa issues but it all boiled down to fiscal residency and in our case the company's willingness to post him abroad.
The 183 days rule applies in the U.K. as you might know to establish fiscal residency. if you become resident in Italy (as soon as you register with the local anagrafe you're a fiscal resident) you have to pay tax and social contributions. A U.K. company might not be able or want to post you here,  as it was the case with my husband. One possibility is for the U.K. employer to use a global employment company such as Oyster HR to mention one.. The other option is to put you on a contract for services and in that case you would be self employed and should be able to apply for the relevant visa. This is as much as we've understood but best to double check facts. There are very good Facebook groups like U.K. citizen's rights in Italy - Beyond Brexit who are way more knowledgeable than me!
Good luck!
-@MonicadFW

sorry I had missed the bit about Milan, of course the FB group British expats in Tuscany and Maremma won't apply! But the other one does and they've been a real help to us many times. I realise my answer doesn't help with the visa issue but I wanted to warn you about all the other implications including social contributions payments if you do move here establishing residency.

This thread is slightly older, so you may want to check out the latest visas for Italy, as just this past month Italy has introduced a visa that might be exactly what you are looking for.