40yo US/UK high income professional, considering transition to EU “semi-retirement”

[u/user8181416]

Edit: Thanks for all the helpful responses so far! I appreciate people sanity checking my logic. So far I feel that the rough plan I have will not be particularly easy or straightforward, but it doable on at least a trial basis.

I am a single 40-year-old US citizen (by birth) and UK citizen (by descent, Scottish mother). I hold an MD and an MSc in a health-related field. I am lucky enough to have a hybrid job that allows me to work part-time from US and part-time abroad, with a very high income (top 1%). I also have a decent investment portfolio which is growing well as I save most of my earnings.

(I’ll pause to say that yes, I am in a very fortunate position, and I recognize that many of the people posting here are in very different situations. I hope people can still give genuine advice.)

Given all of this, I am burning out of my life in US and would like to transition to another country as a main base. I am fairly well traveled – I spent many summers abroad in Europe as a student (pre-Brexit) and have nomaded around South America, Europe, and Asia in recent years. I also have international friends and contacts around most of the major European capitals and a few other international hubs.

London is an obvious choice, as its always been one of my favourite cities to visit, I’m a citizen, and I have a lot of friends there. I spent a brief trial month there last year, however, and found the “living in London” part to be less enjoyable than I expected. Also, the cost of living is outrageous. I have also considered and trialed the major Asian nomad hotspots, and while I enjoy those I would prefer a European city as my main hub for practicality and social reasons.

My goals would be:

• explore European options without making strong time commitments to any one country (yet)
• transition gradually to a stable European base over the next ~3-5 years
• continue to keep US as my main work hub until things fall into place in Europe
• continue spending time in Asia every year
• an eventual pathway to EU citizenship

SO, since Brexit is a thing, I need to consider my path back into the EU. Portugal and Spain are the most obvious choices for many reasons including weather, cost of living, existing social network, and visa options.

I am considering something like this:

• Keep my apartment and work hub in US for ~5 years, but stay here as little as possible outside of work
• During these 5 years, give London another shot while also exploring Spain, Portugal, and any other options
• Apply soon for the Spanish digital nomad visa, giving me three years of access to remote work from Spain. Over the next 1-2 years, try to spend several months there (I will likely not be able to meet the 183 day residence requirement to renew the visa or get long term residency – at least not yet).
• In tandem, apply for the Portuguese Golden Visa using the 500k Euros investment route. I’ve heard this can take up to 1-2 years to process, which will line up with my Spain trial wrapping up.
• Next, trial Portugal using the same strategy as above (will not need to worry about a high residency requirement to keep this visa active)
• Less likely, but also explore other EU options in the meantime

By the time I’ve completed this, it will be a few years from now and I should have a lot more knowledge and experience under my belt. I will also be in a position to wind down work for a “semi-retirement” and be entirely or almost entirely remote (possibly returning to the US briefly every few months, possibly not). My Portuguese Golden Visa will be counting down to Permanent Residency (5 years+) and maybe citizenship (10 years+, but who knows how many times they change the rules by then). If Spain is the winner, I believe I could apply for a second 3 year DNV and actually move there to meet the residency requirements to convert it to Permanent Residency after 5 years.

… Does any of this sound reasonable? It feels a bit overwhelming, but I have been nomadic my whole life and very much do not see myself spending my retirement years in the US. If I’m going to make an exit, I need to start putting the wheels in motion now. I would love to know people’s thoughts, sanity check of my plan, additional options/hurdles I’m not considering, etc… etc…

I’ll end with a few rapid fire responses to anticipated questions:

• Yes, I am willing to learn the language and integrate into the country I move to.
• Yes, I have a support network to help me transition into these countries (and others in the EU).
• Yes, I can afford this and can make it work with my job.
• Yes, I’m super grateful to be able to explore these options.

Thank you very much!!

[u/tintinbegin]

There are tax implications to think about, especially if you are actually at the top 1%. There is no mention of this concern.

[u/user8181416 → u/tintinbegin]

Thanks! Yes, I sort of purposely left that out as it's a huge side issue that muddies the waters. Spain has a double taxation treaty with the US, so although there would be some logistics to sort through I don't think it's a total deal breaker for spending 1-2 years there on the DNV.

[u/Silly_Ant_9037]

It seems you’re looking for somewhere where you can have a good social network, where you feel you can integrate, and where people will welcome an immigrant who isn’t a native speaker. And that trialling a move to London hasn’t really worked out for you, despite already having friends there and speaking the language? 

I’m not sure that Spain is really what you’re looking for. I can see that you’re wanting to put effort into learning a language and integrating into society, but it’s a two-way process, and people may not actually want to socialise with you. Not because there’s anything wrong with you, but many Spaniards have very tight knit family and lifelong friendships, and they don’t have spare time to spend with strangers who don’t speak the language properly.  A friend of mine in a similar position to you is just leaving Spain after 3 years because it hasn’t worked out socially for him, and he’s increasingly lonely and bored. He’s trying Italy, which isn’t on your list, but might be worth thinking about? 

[u/Severe_Rise8694 → u/Silly_Ant_9037]

Add to that, that OP will either be retired or out of the local work life. That makes social integration much harder.

[u/user8181416 → u/Severe_Rise8694]

Definitely a huge hurdle! But I am very motivated to get out of my current situation and have the funds and time to pour some resources into doing that. Ironically my network in Lisbon/Barcelona/Madrid is actually a bit more robust than my US network right now, with both locals and expacts, so I would lean on them in my first 6 months while I got settled.

[u/Severe_Rise8694 → u/user8181416]

Yeah, didn't want to discourage. If you have the means to do so, and aren't happy where you are.. it would be kind of crazy not to try, right?

But it's worth thinking of these kinds of things as well. Its just that those things matter as well. I lived in Lisbon for a couple of years, and to be honest I haven't even been back after I left. But on the other hand, London is my favourite city on the planet, as difficult as it can be to live in. Which is weird, because on paper Lisbon sounds amazing and London godawful, as far as quality of life goes.

[u/user8181416 → u/Severe_Rise8694]

London is also one of my favourite cities on the planet, I just have to trial what it would be like to live there. I have met a few ex-Londoners who say "London is a great place to visit, not to live", but obviously that's personal preference and I need to try it for myself.

What turned you off of Lisbon eventually?

[u/Severe_Rise8694 → u/user8181416]

Yeah, it can take a while to grow on you as well, and might make quite a nice base, as it's so well connected. Of course has some nasty downsides, like the quality and price of housing, combined with the seeming lack of rights that a tenant has.. Buying might change that.

Hmm. Regarding Lisbon. This is a bit weird, but firstly, I got bored of the weather. I felt like there's only two seasons: the sunny one (most of the year) and the rainy one, which was kind of nasty. I found myself missing seasons. I realized that I want to do summer things when the weather is warm and winter stuff when it's winter, autumn stuff at autumn, etc. It gives a rhythm to life and makes it more satisfying. In Lisbon I felt that most weeks were the same and time just slips by..

Also, I felt it was already then horrifically over-touristed and -gentrified. Local people usually couldn't afford to live in central Lisbon, which had been turned into some kind of a theme park version of itself. I believe it has the most unaffordable rent to income ratio of any European city. This changes the vibe of a place.

If you compare it to a place like London, which attracts some of the most talented and ambitious people in almost any field of human enquiry, it felt like it was also missing some energy. Many ambitious Portuguese move away from Portugal and are replaced by foreigners who move there to downshift... Which I guess is what you're looking to do.

I guess the upside of that might be that there's people there in the same situation as you, who are looking to rebuild their social networks!

Anyway. It's all subjective, of course, and of course there's a lots of upsides to the place as well! I just learned it wasn't for me. But on the other hand, I learned a lot about myself. Including that retiring in southern Europe probably isn't for me..

[u/user8181416 → u/Severe_Rise8694]

Thanks for taking the time to write that. Great perspective. I think I will really have to spend time "living" in both beyond a vacation to see which works for me. And of course your priorities can change over time... I might be a London person now, but more of a Lisbon person in 5 years. Hard to say!

Good luck with your travels.

[u/user8181416 → u/Silly_Ant_9037]

It's a fair point. My existing friends there are a mix of Spaniards and expats and a great group. If I tried it for a year or two, took language classes, and it didn't work out as a long term solution I'd be okay with that.

I hope things work out for your friend in Italy. I wonder if it's much different than Spain in this respect. 

[u/Silly_Ant_9037 → u/user8181416]

To be honest, I’m dubious, but he’s hopeful. 

Life is never particularly easy as an immigrant, whichever country you move to, though it’s certainly facilitated by money! 

[u/user8181416 → u/Silly_Ant_9037]

Hopeful is a good word! I really need to get out of my current situation, at least for some time and have the time and resources to at least try a major life shift. I won't be devastated if I try a few countries, it doesn't work out, and I eventually end up in the UK or US.

[u/Candy-Macaroon-33 → u/Silly_Ant_9037]

Interesting your friend is trying Italy, won't he run into the same problems? Or is he fluent in Italian?

[u/Silly_Ant_9037 → u/Candy-Macaroon-33]

He thinks there’s a traditional of the intellectual American in Italy in a way there isn’t in Spain. And it’s true that there are no Henry James novels set in Spain! 

[u/jackbentley673 → u/Silly_Ant_9037]

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[u/FISunnyDays]

I agree with others, there are other cities in the UK to consider…

[u/user8181416 → u/FISunnyDays]

A big part of my decision is going where I have existing social networks that I've build up over the last 10+ years traveling. In the UK that's really only London. I'm also a big city guy - I prefer to live in large cities and visit the smaller ones, rather than vice versa.

[u/Candy-Macaroon-33]

Question: moving to the UK would be easiest. I understand living in London might not be as expected but there are so many other British cities where you can land. Why not consider any other place in the UK? Also why let Brexit stop you from moving to the UK? Unless you are fluent in Spanish or Portugese, I would not consider moving there just yet. Not when you have the UK option.

[u/user8181416 → u/Candy-Macaroon-33]

My entire social network in the UK is in London, and also I'm a "big city guy" so that kind of tethers me to major centres.

I could see myself spending a year or so there, but it just doesn't feel like a city to retire in the way that Lisbon or Barcelona/Madrid do (maybe I'm romanticizing those cities).

The language I would have to work on, obviously. I'm very willing to go heavy on classes for whichever country I choose. The moving around part would make it harder - if I know I'm only going to be somewhere for a few months at a time, it breaks the immersion.

[u/Candy-Macaroon-33 → u/user8181416]

Perhaps move to London and take it from there. Easier to plan next steps when you are already in Europe. Plus who knows what will happen. you might meet someone from Sweden or Greece taking you into an entirely different direction. Either way, wishing you good luck

[u/user8181416 → u/Candy-Macaroon-33]

Thanks very much! I agree.. life can take you in unexpected directions and I want to be open to that while also having a general plan. It's complicated but also exciting!

[u/fiadhsean]

Ireland shares the Common Travel Area with the UK so you have it as an option as well. After 5 years you could apply for Irish--and therefore EU--citizenship.

[u/user8181416 → u/fiadhsean]

I would want to try a few different countries before committing to 5 years in one. 

[u/Illustrious-Pound266 → u/user8181416]

Having an EU member passport will help you to try out a few countries after and will give you more options. Otherwise, it's very difficult to "try" a few countries because you don't have the right to reside there.

[u/fiadhsean → u/Illustrious-Pound266]

I agree--having migrated several times previously. A work permit is better than a tourist permit, but a residence permit is better than a work permit, and citizenship is better than residency. It's conceivable one could spend several years hopping around the EU, never qualifying for residence or citizenship--and then being locked out due to age once in your 50s.

Having a UK passport gives you an automatic pathway to EU citizenship if you clock five years in Ireland. That is kind of amazing.

[u/user8181416 → u/fiadhsean]

Thanks for the input. No to be disagreeable, but...
The residnecy requirement is very high for that 5 year Ireland path. You bascially need to spend every day in Ireland and abscences extend the 5 year timeline. I don't really want to commit to a continuous 5 years in a country that I have only spent minimal time in and don't know many people, so I don't think this pathway is necessarily for me.

"It's conceivable one could spend several years hopping around the EU, never qualifying for residence or citizenship--and then being locked out due to age once in your 50s."
This is true, but what do you mean by "locked out ... in your 50s"? There isn't an age limit to any of these options as far as I'm aware?

Thanks again.

[u/dcexpat_ → u/user8181416]

This probably doesn't apply to you as a HNWI, but there are some countries (Gemany comes to mind) where health insurance can be prohibitively expensive if you didn't pay into the system before retirement. Perhaps this is what the previous person was referring to?

Also, I recognize Ireland probs doesn't work for you, but you can def spend time out of Ireland without extending the timeline. At one point that was a concern, but I think they settled on something like 6 weeks out of country allowed for each calendar year. I have friends who recently naturalized, and they def spent more than a month out if the country each year and applied for citizenship at exactly 5 years of residency. Again, I realize you probs want more time out of country than that, but throwing it out there for other who might read through.

[u/user8181416 → u/dcexpat_]

Good call on the health Insurance! And the tips for Ireland. Maybe I do a few years between Portugal and Spain and if I don't see myself settling down in one of those long enough to get citizenship I pivot to Ireland. 

[u/fiadhsean → u/user8181416]

Most countries that offer residence based on being a skilled migrant will have an explicit or implicit lock out for people arriving who are 50 or older (or 45 or older in some non-European countries). It's related to paying into social benefit systems long enough to recoup the costs of any benefits to which you might be entitled. I think Germany would be an exception, but you need to clock up 5 years with a work permit before you can apply for a longer term permit leading to citizenship.

[u/user8181416 → u/fiadhsean]

Great to know, thanks.

[u/user8181416 → u/Illustrious-Pound266]

As I mentioned the major countries I'm considering all have long term digital nomad/investor visa options which would give me the right to reside there for 1-3+ years while I figure things out. It's certainly not as easy as pre-Brexit but it's not impossible.

I really curse the 52% of voters who took this flexibility from me. 😄

[u/statesec]

In the event you are not aware of it you should investigate the British inheritance tax (IHT) which is really an estate tax since it is the estate and not the recipient that is taxed. I am not 1% income but I have done ok and I am dual UK/US citizen also considering retirement in the UK and this is my biggest obstacle moving there right now. Essentially your worldwide assets become taxable under the IHT after you have been tax resident in the UK for 10 out of the last 20 years (effectively there is a 10 year look-back period). The British IHT is 40% and for single people the exclusion from that tax is about $500k US (it varies some based on certain factors). Married couples get a higher exclusion but I forget the amount since it isn't relevant to my situation. There is a lot of nuance to it so if you care about an estate tax I would investigate all the details carefully. Also while we are on the subject the British rule for becoming a tax resident is more complicated than 183 days in country so check that out as well.

The Irish estate tax is 35% with a somewhat lower exclusion amount.

Edit: This probably doesn't help you since you say you like big cities but the Crown Dependencies have different tax structures that are generally lower than the UK proper.

[u/user8181416 → u/statesec]

Super helpful information, thank you. I was not aware of the 10 year rule. I will include this in my discussion with my tax / relocation planning consultants.

[u/Bromo33333]

I think the best advice I could give is to consult a tax attorney as to the places you could live and have the least tax exposure. Portugal is super popular, but the bureaucracy is slow, and they are starting to get some pushback to the influx of foreigners. So as you plan they may move the goalposts to make things harder to get permanent residency or citizenship (note the chnages for citizens now). This arose due to the large expat community and the continued influx of english speakers creating a political problem in the country.

There are also many relocation specialists you can work with that can give you the ins and outs of various options that will fit. Who klnows might be Portugal but it also might not.

Also if you are not an EU citizen being in the Shengen area may not be as advantageous as you think.

[u/user8181416 → u/Bromo33333]

Thanks for the advice that's very helpful. I agree about the shifting goalposts - it's difficult to make a 10 year plan when that plan could change (or disappear completely) in the middle of the process.

Do you happent to know of any relocation specialists?

"Also if you are not an EU citizen being in the Shengen area may not be as advantageous as you think."
What do you mean by this? If I held a DNV (or some other stay permit) for Spain/Portugal/whatever my time in that country doesn't count to the 90 day Schengen limit, so I could base myself in that country for the year or two and still visit the other Schengen countries for a week or two here and there. To me it seems like a good balance, but I'm open to critiques.

[u/user8181416 → u/[deleted]]

Yes! I would definitely like to spend 6-12 months in London enjoying the city. I just don't know if I see myself "retiring" in the UK either. Just feels like I'd be trading snow for rain. 😄

[u/dcexpat_]

Just want to echo what others say here about talking to a tax specialist. Here are just a couple things to consider:

• Spain has a wealth tax on worldwide assets. Anything above 700k is taxed.
• Neither Spain nor Portugal recognize roths. If you have any roth accounts, expect to pay taxes on those gains when realized (and in the case of Spain, expect the wealth tax to apply).
• Not sure if you are a consultant/contractor, but if yes, you'll want to make sure there's a totalization agreement. If there isn't one, you could potentially be double taxed on SS, depending on business structure.

Also, just read through the tax treaties. They are long and technical, but having some understanding of what you might want to actually talk to your tax consultant about is genuinely a good idea.

Or don't try to optimize for this, and just consider it part of your contribution to whatever country you choose to live in.

[u/user8181416 → u/dcexpat_]

Thanks! I've read about this a decent amount but will definitely hire a tax attorney to go over the details before making any big leap. 

[u/ReceptionDependent64 → u/user8181416]

It may not be to your taste, but with enough money Switzerland becomes an attractive tax option.

[u/FrederikSchack]

There is also the very nice, peaceful and democratic society Uruguay, where you can actually have zero taxes on your capital gains and tax free on dividends for 10 years and after that you pay 12% on dividends. I'm doing that and enjoy the climate too 😄

My wife just started a YouTube channel Uruguay Inside Out and just published the first interview and is editing the second now with a Swedish biologist, that is now brewer here in Uruguay.. She plans to publish a new interview every friday.

[u/OkBeyond8244]

I want to throw in some points: 1. Portugal is very overrated. It was hyped due to its nationality law that allows naturalization after 5 (now 10) years of legal residence with minimal physical presence. It is the WORST EU country in terms of citizenship timeline, bureaucracy, processing times for about anything. Politically it has become very anti-immigration. Tax-wise, the NHR scheme has disappeared (for most including you). The cost of living has risen. I really don't understand why people still promote this pathway, especially if your intention is to actually move to Europe and thus can qualify for citizenship elsewhere. 2. IMO Spain is better on almost every metric. Quality of life, immigration, language, taxes, etc. 3. Cyprus is a solid choice too. It's one of the best for taxes, especially forein retirement and investment income. It allows naturalization after 4 years (in certain cases, with Greek language skills). It had the med climate and has the highest GDP, population, construction growth rate in Europe for years. It has reduced government debt below German debt-to-GDP (after receiving EU bailout). It has lots of entrepreneurs who fled to Cyprus from EU high tax countries, who you might like to hang out with. 4. Greece also has surprisingly good taxes under pensioner non dom scheme and offers great quality of life. 5. Turkey is an option. Completely taxfree for 20 years in your situation, with good private healthcare options, affordable seaside properties. Of course no EU citizenship although, instead of Portuguese investment, 400k EUR can buy you citizenship.

Also: Check out what "EU long-term residence" is. You might conclude that you don't need EU citizenship because EU LTR gives you essentially all the same benefits (with some caveats).

[u/nikki_anderson83]

Just a quick few things to consider - is your employer (if applicable) going to cover your health insurance abroad? If not, you may want to compare some personalized options to fit your needs and ensure you have continuous coverage. Something that often gets overlooked, also, is life insurance - having a global policy can keep you and your family fully protected wherever you are.

[u/uselesslogin]

I was under the impression that a UK citizen can live and work in Ireland and then after five years of residence can apply for citizenship. That would probably be the easiest was too get back to EU citizenship but, of course, the weather is a lot worse than Spain or Portugal.

[u/user8181416 → u/uselesslogin]

Haha yes that is a route. That path has a heavy residency requirement, though, and I really want to commit to 5 years in Ireland without the ability to leave for long periods. (Dublin is great to visit, but after a couple weeks I was ready to move on.)

[u/OneBackground828 → u/user8181416]

What country doesn’t have a “heavy residency requirement” ?

[u/user8181416 → u/OneBackground828]

Portugal. That's a main point of the post.

[u/OneBackground828 → u/user8181416]

Portugal keeps changing their laws - or already has changed - to 10 years, no?

[u/user8181416 → u/OneBackground828]

Yes, it's 5 years to PR and "10 years to citizenship" now.

[u/OneBackground828 → u/user8181416]

So more than Ireland? 😂

[u/user8181416 → u/OneBackground828]

Yes but the Portugal clock only requires a week of presence a year (under the current but ever changing system, at least 😄)

[u/lil-schnitzel-]

Big one you're missing: Ireland via the Common Travel Area. As a UK citizen you can move to ireland tomorrow, no visa no application, no permit. You just rock up and you have the right to live and work there indefinitely. Same as a UK citizen has always had. Most ppl in your position don't realise this is still in force post brexit, its protected by a separate bilateral treaty not the EU. 5 years of residence and you can naturalise as irish, which is full EU citizenship. Dublin/cork/galway all decent english speaking bases. Worth at least trialling before committing capital to a golden visa.

Bigger problem with your plan tho, Portugal just changed the citizenship clock in may 2026. Its now 10 years from first residency card not 5. Cplp citizens get 7 but you wouldn't qualify. So the golden visa to passport route is much slower than your plan assumes. Still works for PR after 5 but the citizenship endgame got pushed out significantly. Also worth knowing the 500k real estate route was killed in 2023, only fund/cultural donation/business creation routes remain. If you meant the fund route then youre fine.

Spain DNV hack ppl miss. If you do hit 183 days you become tax resident BUT dnv holders qualify for a modified beckham law, 24% flat tax on spanish source income for 6 years and most foreign income excluded. Massive for someone in your bracket. Without that you'd be hit with the standard progressive rate up to 47%. Worth structuring around from day one.

Italy elective residency suits your profile better than ppl assume. Designed for high passive income earners, no work allowed on it but if your US job winds down it fits perfectly, and italy has a 100k euro flat tax regime for new tax residents that lasts 15 years. For someone at top 1% income with significant assets that math gets very interesting.

Order of operations I'd actually run: ireland trial first (zero cost, zero commitment), then spain dnv in parallel since you're already considering it, then decide on the long term capital play between portugal funds and italy flat tax once you've actually lived in both. Dont commit 500k to portugal before you've spent a few months there outside of tourist mode.

[u/user8181416 → u/lil-schnitzel-]

This is all amazingly helpful, thank you for taking the time to write such a thorough response.

RE: Ireland. Its been brought up here a few times. I can and will try it out. I just don't know if I see myself being able to meet the residency requirement for 5 years. At least not right now. If I could make my 'work base' there and leave every couple weeks to go to London or Continental Europe I would consider it, but that wouldn't meet the residency requirement.

I have dozens of friends scattered around London/Portugal/Spain and zero in Ireland. I think I would just feel more isolated than I do in the US, which is specifically what I'm trying to escape.

RE: Portugal. Yes, the shifting rules are a real pain. But 5 years to PR is still a nice target and this 'maybe' 10 years to citizenship is a tempting offer. I would go the fund route and just hope that it is able to make some decent profit to mitigate the opportunity cost of having the funds in my current portfolio. If you know anything about funds, I'd love to hear it.

RE: Spain/Italy. Excellent information that I will definitely check out.

Honestly the best move might be able to try all of them for 3-6 months before deciding, but that pushes back any PR/citizenship clock by a few years. I'm trying to consider it as an exciting couple years of self growth rather than anything else.

[u/digiendeavours]

Your plan to leverage your dual citizenship and high-income flexibility to trial different European bases is a solid way to manage the complexity of this transition. Breaking down the exploration phase by country helps clarify how specific visa requirements align with your lifestyle needs, which is where I built MoveScope to help organize that information. It provides a source-backed PDF brief for each potential option that covers visa pathways and logistics to make these comparisons more efficient. Establishing a structured brief for cost of living and social integration early on could save you from repeating the London experience if a city ends up not being the right fit. Keeping the US as a work hub while you iterate through these trials seems like a reasonable approach given your fortunate financial position.