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We’re going to take real cases in this article and our posted live stream from our YouTube subscribers and assess which Italy residency program makes sense for each specific case. No theory, no generic advice - real people, real budgets, real circumstances, and real solutions. Either submit your case in the live chat during our LIVE sessions here every Thursday at 11am EST and we’ll assess your best Italy pathway live or email us at '
In all these case studies we are covering today to obtain the Italian residency for yourself and your family, the investor visa category is possible, meaning if you have €250,000 to invest in a startup or €500,000 to invest in a public or private Italian company, you can potentially qualify and obtain your residency withing 3 months (as long as you have the money and a clean background check). However, the purpose of this article and live stream to walk you through various case studies if you are seeking other options and are looking for custom advice on your specific case. The investor visa is almost always possible and also a good and fast route, but you need to know ALL your options before you can decide for your residency to Italy. Similar to making any financial investment decision, where you obtain advice from your financial advisor or banker, they’re not going to give you just one option. And that’s also very important in the global mobility, residency and citizenship industry – providing you options and educating you on what’s possible and what isn’t.
There are several reasons for seeking a residency in Italy:
We have received several emails from our audience members asking us to assess their cases for Italy – to obtain a residency in Italy. We have removed all personal information and stripped it to the main facts of the case, in order to make a custom assessments AND have other readers and audience members be able to compare their own profiles against these case studies.
We have to take out a ‘Factual Time Out’ before we proceed…..What’s a factual time-out? It’s to fill you in if you don’t know the difference on all the Italian residency programs we are using in our assessment for the cases that have been sent to our by our readers, subscribers and audience members.
All these programs for the Italian residency (Digital Nomad, Freelance, Representative Office) can lead to permanent residency in 5 years and citizenship in 10 years, based on the qualifications. And they have the same residency requirements as the investor visa. They have the same flexibility of residency requirements, eligibility for PR and citizenship as the investor visa program of Italy.
Reach out to us to request the comparison table of ALL the Italian residency options.
Case Study 1: An American Remote worker (consultant) on payroll or has their registered S-Corp from the US with $45,000 annual income, family of 4, planning to move to Italy by September 2025.
This applicant can easily qualify for the Digital Nomad Visa in Italy which also provides residency that can be converted to PR and eventual.
Digital Nomad visa requires min. €28,000 annual declared income in addition to the below requirements:
The timeline can be 4-6 months to be processed and arrive to Italy, which is the only drawback in terms of timelines.
In case this applicant also has an S-Corp with more than 1 shareholder, in order to provide Schedule C tax as proof of the operations from the past fiscal year, having revenues of more than €12,000, they could also use the Representative Office visa program which we will cover in the new few case studies.
Of course, the investor visa can also be applied if you have €250,000 or €500,000, then convert to a Freelance visa, and take out your initial investment taking advantage of both programs combined – stay tuned for the next case studies where we explain to you how this is done.
Healthcare eligibility in Italy under the Digital nomad visa: You will need to register voluntarily and pay the same €2,000 annual fee to access the SSN.
Minor children can study for free in elementary or secondary/high school under the digital nomad visa program. The residence permit for family reasons allows access to enrollment for study purposes.
You and spouse or common-law are authorized to work in Italy under the digital nomad visa. The residence permit for family reasons allows the holder to work in Italy.
Case Study 2: Self-Employed American who owner and runs his/her own company and planning to move to Italy with spouse
Running your own company can mean you are 100% shareholder or even 1% shareholder but are being paid by the company you have equity in.
I would recommend the rep office for you because you are either a director or shareholder of company, based on last year’s financial tax filings for the corporation. You don’t need to be a shareholder necessarily (it could be either or). Nonetheless, as we covered in the last case study, if you have an S-corp and not more than 1 shareholder, you will not have a Schedule C to qualify for this specific Italian residency program. However, if you do have a C-Corp or an S-Corp with more than 1 shareholder, or any other corporate structure where you are either a director or shareholder, then you will qualify. The requirements of the Representative Office program are:
There is no legal entity registered for the American company in Italy, and no bank account or fiscal or tax implications. However, for the first renewal you will need to have payroll which is why we recommend converting to freelance inside Italy before this Rep office renewal milestone. Freelance visa applications inside Italy do not have a quota and you can qualify easily by proving that you have a minimum of €10,000 annual income and can skip the payroll steps from the overseas entity which has sent you as a representative.
You can also qualify for the digital nomad visa or the investor visa leading to a residency in Italy, similar to the rep office visa program.
This program also offers free education enrollment for minor children, and work authorizations for the main applicant and spouse.
Healthcare eligibility in Italy under the Rep office visa will require the individual to be considered a posted worker and is typically entitled to free registration with the SSN, provided the secondment is recognized and compliant with applicable Italian regulations (including proper registration with INPS and relevant documentation such as the A1 certificate, if from the EU).
Case Study 3: American Retiree with €2M but wants flexibility to go back and forth between Italy.
Whether the applicant has active income or not doesn’t matter for this specific case study.
Many people would think the elective residency would be a good choice, but we wouldn’t recommend this due to the many restrictions of the program. We would recommend applying through the investor visa program of Italy, and utilize a directed IRA towards an investment in Italy for this program. This is possible and you can put your financial advisor in touch with our team to explore this option.
Healthcare eligibility in Italy under the Investor visa program: Unfortunately, these applicants are not entitled to free registration with the SSN. However, they may register voluntarily by paying an annual flat fee of €2,000.
Both the main applicant and the spouse/common-law are authorized in case they want the option of working inside Italy.
No tax residency is required during the time they are temporary residents, even if they stay more than 183 days a year in Italy.
Case Study 4: Young entrepreneur with common-law partner, limited capital and planning to move to Italy before the end of 2025.
We would definitely recommend the digital nomad and all you need to qualify is annual income min €28,000 in addition to the requirements we listed in case 1 above.
Healthcare eligibility in Italy: The applicant is expected to register voluntarily and pay the same €2,000 annual fee to access the SSN.
Minor children can study for free in elementary or secondary/high school under the family reunification provisions.
You and spouse or common-law are authorized to work in Italy based on the family reunification provisions of the Italian immigration law.
Case Study 5: Early Retired couple who can’t access their retirement/pension yet.
So you are an American couple who can’t access your 401K or self-directed IRA yet, and are looking for an efficient way to obtain a residency in Italy but are not in a huge rush.
You don’t have many options available but here are some potential solutions and pathways to obtain your Italian residency:
No authorization to work under the elective residency program.
Case Study 6: Freelance American consultant with income as an independent contractor, no existing company or payroll, planning to apply to move to Italy
The Freelance visa is the best option for this applicant to apply for their residency in Italy. The downside for this program is that there is a quota of approx. 1500 a year, meaning your application could be refused purely due to the quota having run out (technical refusal). Sometimes applying on the 2nd of January might increase the chances of being approved vs. during the second half of the year. The freelance visa requirements are minimum of 3 years proof of work experience, and proof of minimum income of €10,000 per year.
Of course, this applicant can also apply for the digital nomad visa, which may be safer and higher chances of approval from outside Italy instead of the freelance visa.
We want to make sure you get the most out of your time reading our articles and watching our LIVE streams on YouTube– by doing real life custom assessments for various residency programs. Whether it’s Italy, other European jurisdictions, Panama, Canada, USA, New Zealand or fast passports – we can make it happen.
If you are ready to put your Plan ‘B’ into action, for yourself, your family or perhaps your clients, you can reach out to us here. Join our online live stream every Thursday at 11am EST, or 8am PST, to share your feedback, post your questions, and engage with others who are also exploring these opportunities – just by clicking on our YouTube channel link down below.
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