So You Want to Live Abroad for a Few Months — What People Like Us Actually Need to Know
Updated: Aug 24
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There is a particular kind of fantasy that starts creeping in somewhere around your early fifties. You are sitting at the fire pit, yes, in February, yes in Wisconsin, yes that is exactly as cold as it sounds, and someone says, "we should just move to Italy for a few months."
Everyone laughs. Someone refills their drink. And then nobody stops thinking about it.
If that sounds familiar, you are in good company. The idea of spending a season somewhere else, somewhere warm, somewhere beautiful, somewhere with good wine and no polar vortex, has moved from a retirement daydream to something people are actually doing. People our age. People with a condo back home and a group chat full of friends who are starting to wonder the same thing.
So, let's actually talk about it. Not the fantasy version. The real version. What it costs, what you need to know, what nobody tells you, and why it might be more doable than you think.
The One Thing You Need to Understand Before You Plan Anything in Europe.
Here is the rule that stops a lot of people cold when they first look into this: Americans are limited to 90 days within any 180-day period in the Schengen Area. The Schengen Area covers most of Europe: France, Spain, Italy, Portugal, Greece, and 22 other countries all share that same 90-day clock. It is not 90 days per country; it is 90 days total across all of them combined.
That means if you are dreaming of three months in Tuscany followed by a month in the south of France, you need a visa for that. A tourist stay gets you 90 days and that is it.
The good news is that 90 days is actually a solid chunk of time. A full summer. A whole winter escape. And for a lot of people, that is exactly what they were picturing anyway. If you want to stay longer, countries like Portugal and Spain have long-stay visas specifically designed for retirees and people with passive income, we will get to those. But if you are thinking two or three months, the 90-day rule works in your favor, and you do not need to do anything complicated.
Where People Like Us Are Actually Going — And What It Really Costs
Let's look at the four destinations that come up most consistently for midlife Americans doing extended stays. Real numbers, real tradeoffs.
Mexico
Mexico is the most accessible option for Americans doing their first extended stay abroad, and the numbers make it very easy to understand why. A single person can live comfortably on $2,000 to $2,500 per month. The private healthcare system is excellent and dramatically cheaper than the US, a visit to a specialist runs about $50, and private insurance for someone in their 60s costs roughly $1,500 to $3,000 per year. Many doctors speak English and have US training.
Mexico also does not have the 90-day Schengen rule to worry about. Americans can stay up to 180 days as a tourist, and a temporary residence visa is available for longer stays with relatively straightforward income requirements.
San Miguel de Allende, the Riviera Maya, Puerto Vallarta, and Lake Chapala are the most popular areas for American expats, each with established English-speaking communities that make the transition significantly easier.
Portugal
Portugal consistently tops the lists for midlife Americans looking at Europe, and it has earned that spot. The cost of living is meaningfully lower than most of Western Europe, outside of Lisbon, you can find two-bedroom apartments for well under what you would pay in any mid-sized American city. A couple can live comfortably for around $2,500 to $3,500 per month depending on location and lifestyle.
Portugal also has a long-stay visa designed specifically for people with passive income, pensions, retirement accounts, investments, that allows you to stay legally for a year at a time with the ability to renew. After five years you can apply for permanent residency. After ten, citizenship is possible if you want it.
The Algarve region in the south is stunning, warm, and full of expat community. Lisbon is vibrant and walkable. The Douro Valley is wine country. There is a lot of Portugal to love.
Spain
Spain offers 300-plus days of sunshine per year in many parts of the country, a deeply social culture built around long dinners and late evenings, and a cost of living that lets a couple live well, really well, for about $2,400 to $2,800 per month. The food culture alone might be worth the visa paperwork.
Spain's Non-Lucrative Visa is the primary route for retirees and people with passive income who want to stay longer than 90 days. It requires proof of sufficient income and private health insurance, and it is renewed annually. It does not allow you to work in Spain, but for someone living on retirement income or a pension, it is a clean and workable option.
The Costa del Sol, Valencia, Seville, and the Balearic Islands all have large established expat communities with English-speaking services, doctors, and social networks already in place.
Greece
Greece leaped to the top of nearly every 2026 retirement and expat ranking, and the numbers explain why immediately. A couple can live on roughly $2,500 to $3,000 per month including rent, and many expats report spending about one-third of what they were spending in the US while genuinely upgrading their quality of life. A three-bedroom home with sea views outside of Athens can rent for $800 to $1,000 per month. Let that land for a second.
Greece has over 300 days of sunshine per year and a pace of life that is — and this is a direct quote from expats who live there — "siga siga." Slowly, slowly. Which after a career, after raising kids, after years of being everything to everyone, sounds like exactly what the doctor ordered.
The Healthcare Question Nobody Wants to Ask
Let's just say it out loud because everyone is thinking it: what happens if something goes wrong while you are abroad?
This is the question that stops more people than any other, and it deserves a straight answer.
For a short stay of 90 days or less, most Americans handle this with a travel insurance policy that includes medical coverage. These are widely available and more affordable than most people expect. Travel insurance typically runs 4% to 8% of your total trip cost, but for extended stays where you are renting rather than booking a package, a travel medical policy is the more relevant option. For a 60-year-old traveler, a travel medical policy for a 60-to-90-day international trip typically ranges from around $120 to $400 depending on coverage level and deductible, meaningful money, but not a budget-breaker when you are already saving significantly on monthly living costs compared to home. One important note worth knowing: Medicare does not cover you abroad in most cases, so if you are on Medicare, a travel medical policy is not optional — it is essential. Mexico's private hospitals are internationally accredited and significantly less expensive than US care. Spain and Italy both rank among the top countries in the world for healthcare quality.
If you are staying longer and pursuing a visa, most long-stay visa programs in Europe require proof of private health insurance as part of the application anyway, so it gets built into the process rather than left as an afterthought.
The bottom line is that healthcare abroad, particularly for a planned seasonal stay with healthy adults, is manageable. It requires research and the right insurance policy, but it is not the dealbreaker it feels like before you look into it.
What Nobody Tells You About Having a Home Base Abroad
Here is the part of this conversation that the generic "retire abroad" articles always skip, and it might be the most compelling piece of all.
When you have a home base somewhere beautiful, people come to you.
We have friends who spent an extended stay in Spain. And while they were there, a handful of us were able to take trips — real international trips, the kind that usually feel out of reach — at a fraction of what they would normally cost. Why? Because we had a place to stay. We had a built-in local who knew where to go, what to skip, and how to avoid looking like a tourist. We had someone who had already figured out the transportation and the neighborhoods, and which restaurants were actually worth it.
It changed the entire experience. We were not tourists staying in a hotel trying to piece together an itinerary from a travel blog. We were guests in a real home, in a real neighborhood, living something closer to actual life there.
And there is another facet to this making it extremely attractive, your adult kids would come. Your grandkids would come. The people who would never in a million years book a European trip on their own would get on a plane to come see you. Flights within Europe once you are already there are extraordinarily inexpensive, you can hop to another country for what you would spend on a nice dinner. A two-week visit from your son or daughter becomes a trip they will talk about for the rest of their lives, anchored by the fact that you were already there, already settled, already ready to show them around.
That is not a footnote to the experience. For a lot of people, that becomes the whole point.
The Condo-as-Home-Base Concept
For people who are thinking about downsizing, or who already have, this is where the math starts getting genuinely interesting.
The traditional assumption is that you need a house, a yard, a full life infrastructure at home before you can even think about being somewhere else for a few months. But an increasing number of people in their 50s and 60s are flipping that script. Downsizing to a condo intentionally — not because they have to, but because a lower-maintenance, lock-and-leave home base gives them the freedom to actually go somewhere for a season without worrying about what is happening back home.
A condo with a HOA that covers exterior maintenance is not a consolation prize. For someone who wants to spend two months in Portugal, it is a strategic choice.
The Honest Bottom Line
None of this requires you to sell everything, learn a new language fluently, or make a permanent decision about the rest of your life. What it requires is research, a passport, a decent travel insurance policy, and the willingness to try something that most people only ever talk about at the fire pit in February.
The people doing this are not wildly wealthy or particularly adventurous by nature. They are people who decided that the daydream was worth taking seriously. They looked into it, made a plan, and went.
You can do the same. And if you end up in Spain for a couple of months, know that your people will find a way to get there.
We always do.
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