She arrived in Cascais with a plan.
Three-bedroom apartment with an ocean view. Portuguese lessons starting Monday. A book club to join, yoga classes to take, a whole new life waiting to unfold. Her retirement savings stretched further here than they would in Connecticut. The healthcare was supposed to be excellent. The weather was supposed to be perfect.
Sixteen months later, she was on a flight back to Hartford, her Portuguese never progressing past “obrigada” and “desculpe,” the ocean-view apartment now someone else’s dream.
I met her story through a mutual friend, but I’ve since met it dozens of times. Different women, different cities, different specific circumstances, but the same arc: hopeful arrival, gradual disillusionment, eventual departure.
The statistic in my title is approximate, derived from conversations with relocation consultants, expat community organizers, and the women themselves. It’s not a formal study. But every professional I’ve spoken with confirms the pattern: American women over 55 who come to Portugal alone leave at dramatically higher rates than couples, men, or younger women.
The reasons why are uncomfortable to discuss because they challenge the sunny narrative we want to believe about reinvention abroad.
Quick and Easy Tips for Staying in Portugal Long-Term
Spend at least three to six months in one location before committing permanently. Short visits rarely reveal seasonal changes, service availability, or neighborhood dynamics. Extended stays provide realistic insight.
Invest early in language learning. Even basic conversational Portuguese dramatically improves healthcare access, social relationships, and daily confidence. This effort pays off quickly.
Build a mixed social network. Connect with both locals and expats to avoid isolation. Relying only on expat groups can limit cultural integration and long-term satisfaction.
Plan for aging-related needs. Research mobility services, transportation options, and nearby medical facilities in advance. Long-term comfort depends on accessibility.
One of the most misunderstood aspects of retiring or relocating to Portugal is the assumption that lifestyle alone guarantees happiness. Sunshine, beaches, and affordable living attract many American women, but daily realities often clash with expectations built from social media and travel blogs.
Another controversial issue is social isolation. While Portugal is friendly, deep friendships take time to develop. Many newcomers underestimate how difficult it can be to build meaningful connections without fluency in Portuguese or long-term community ties.
Healthcare is often praised in expat circles, yet navigating the system can be frustrating. Public healthcare involves wait times and complex registration processes. Private healthcare, while affordable, still requires learning new procedures and providers.
There is also debate about independence and aging abroad. Transportation limitations, language barriers, and unfamiliar bureaucracy become more challenging over time. What feels adventurous at first can slowly become overwhelming.

Reason 1: The Loneliness Trap Is Deeper Than Anyone Admits
Loneliness is the number one factor driving departures, but not the obvious kind of loneliness. Not “I have no one to talk to” loneliness—most of these women socialize frequently. It’s something more subtle and harder to fix.
Expat communities in Portugal are organized around introductions, not depth. You meet people at “Newcomer Meetups” and “Expat Coffee Mornings.” You exchange pleasantries with dozens of friendly faces. You are never alone in the technical sense.
But building genuine friendships as an adult takes time—research suggests close friendships require approximately 200 hours of shared experience. In your home country, you had decades to accumulate those hours. Here, you’re starting from zero.
For women over 55 arriving solo, the math is brutal. The expat community constantly churns: people arrive, people leave, people relocate within Portugal. Investing heavily in a friendship only to have that person return to the US in 8 months happens repeatedly. After a few cycles, you stop investing as deeply.
Meanwhile, integrating with Portuguese social circles proves nearly impossible without fluent Portuguese. The Portuguese are famously warm and welcoming, but their social lives revolve around family networks and friendships built over decades. Breaking into these circles as a 58-year-old foreigner is not a reasonable expectation for most.
One woman I spoke with described it perfectly: “I was never alone. I was constantly lonely.”
The distinction matters. You can be busy with social activities and still lack the one thing humans need: people who truly know you, care about your day-to-day life, and would notice if something went wrong.
In Hartford, her neighbor of 30 years would notice if she didn’t take in her mail. In Cascais, nobody would notice for weeks.
Reason 2: The Healthcare Fantasy Collides with Reality

American women moving to Portugal in their late 50s and 60s are often managing chronic health conditions. High blood pressure, thyroid issues, arthritis, early-stage diabetes—the conditions that don’t prevent a good life but require regular management.
Portugal’s healthcare system is genuinely excellent. But accessing that excellence as a non-EU foreigner is more complicated than the relocation blogs suggest.
The public system (SNS) is available to residents, but appointments can take months for non-urgent issues. The specialists who speak English are concentrated in Lisbon and Porto. If you live in the Algarve or Silver Coast, you may travel hours for appointments.
Private insurance solves the access problem but creates new ones. Pre-existing conditions are either excluded or priced punitively. Women in their 60s report premiums of €200-400/month for comprehensive coverage, with restrictions on what’s actually covered.
Then there’s the pharmacy challenge. Medications available freely in the US may require new prescriptions in Portugal, new Portuguese doctors willing to prescribe them, and occasionally substitutions when the exact brand isn’t available.
Several women I’ve spoken with reported spending the first 6 months in Portugal essentially re-establishing their entire medical care from scratch. Finding a GP who speaks English, getting referrals to specialists, translating medical records, adjusting medications. It’s exhausting when you’re healthy. It’s overwhelming when you’re managing conditions.
One woman returned to the US after her cardiologist in Portugal recommended a different medication protocol than her American doctor had. She didn’t know whom to trust, couldn’t evaluate the advice herself, and decided she’d rather deal with American healthcare costs than Portuguese healthcare uncertainty.
Reason 3: The Language Barrier Never Lifts

This reason is uncomfortable because it implies a failing on the part of women who leave. But it’s honest: most American women over 55 do not achieve conversational Portuguese despite genuine effort.
Language acquisition slows with age. This is neurological fact, not failure of will. A 58-year-old learning Portuguese faces a steeper climb than a 28-year-old, even with identical study habits and motivation.
Portuguese specifically is challenging for English speakers. The pronunciation is harder than Spanish. The grammar has complexities (subjunctive mood, personal infinitive) that don’t exist in English. And European Portuguese sounds dramatically different from Brazilian Portuguese, so all those Brazilian telenovelas you watched don’t help as much as you’d hoped.
Most women arrive planning to learn Portuguese. They take classes, use apps, practice with tutors. After a year, they can order food, handle basic transactions, and follow about 30% of conversations around them.
That’s not enough.
Thirty percent comprehension means you’re missing most jokes, most nuance, most of what makes conversation actually enjoyable. You’re exhausted from constant partial understanding. Every interaction requires extra cognitive effort. You start avoiding situations that require Portuguese because they’re stressful rather than fun.
The women who stay long-term fall into two categories: those with exceptional language aptitude who achieve fluency, and those who accept permanent linguistic limitation and structure their lives around English-speaking contexts.
The women who leave are often in the middle: they wanted to integrate, couldn’t achieve the fluency required, and found the permanent semi-comprehension state unbearable.
Reason 4: The “Independence” That Became Isolation

Many women who move to Portugal solo are making a statement about independence. They’re proving—to themselves, to their families, to the world—that they can do hard things alone. The move itself is the accomplishment.
This framing creates a psychological trap.
Asking for help feels like admitting the independence project has failed. Acknowledging loneliness feels like admitting you can’t handle being alone. Returning to the US feels like admitting you made a mistake.
So women stay longer than they should, performing independence while actually suffering. They post beautiful photos on Facebook showing the ocean, the pastéis de nata, the charming streets. They don’t post about crying in the bathroom, again, because something small went wrong and they had nobody to call.
The compounding effect of small difficulties without support is underestimated. In a couple, you can vent to your partner when the bureaucracy frustrates you. Alone, the frustration just accumulates. In a couple, small daily logistics get shared. Alone, you handle everything yourself, always.
This isn’t about competence. These women are competent. They’ve run households, raised children, built careers. But competence is different from emotional support. You can be fully capable of solving your own problems and still need someone to care that you had problems to solve.
The independence narrative prevents women from acknowledging when the solo version of expat life isn’t working. By the time they admit it to themselves, they’re often deeply unhappy and ready to leave immediately rather than gradually.
Reason 5: The Numbers Don’t Work for Single Women
This is the most practical reason and perhaps the least discussed: the financial math of solo expat life is worse than the financial math of coupled expat life.
A one-bedroom apartment in Lisbon costs €1,200-1,500/month. A two-bedroom costs €1,400-1,800. A couple in a two-bedroom pays €700-900 each. A single woman in a one-bedroom pays €1,200-1,500 alone.
The same pattern holds across spending categories. Restaurant meals, utilities, transportation—everything that’s fixed or semi-fixed costs more per person when you’re one person.
Single women also face rental market discrimination. Landlords prefer couples to single tenants, especially older single women they perceive as higher risk. Finding good apartments takes longer and sometimes requires paying more.
Healthcare insurance is per-person with no couple discount, so single women pay the same absolute amount as coupled individuals while having no one to share other costs with.
The cumulative effect: single women over 55 need approximately 25-30% more monthly budget than coupled individuals to maintain the same lifestyle. A couple living comfortably on €3,500/month means €1,750/person. A single woman achieving the same lifestyle needs approximately €2,300/month.
This reality collides with retirement planning. Many women calculated “can I afford Portugal?” based on general cost-of-living data that assumes averaging across living situations. They arrive, discover the single-woman premium, and realize their runway is shorter than planned.
Returning to the US, with its lower (comparatively) single-living premium in many areas, sometimes makes financial sense even setting aside all other factors.
The Stories They Tell Themselves on the Way Out

Women who leave Portugal after 18 months rarely cite these five reasons explicitly. Instead, they construct narratives that preserve dignity:
“I miss my grandchildren.” (True, but you knew you’d miss them before you came.)
“My mother’s health declined.” (Possibly true, but convenient timing.)
“Portugal just wasn’t for me.” (Accurate but unexplained.)
“I realized I’m a city person and Portugal is too quiet.” (Rarely the actual reason.)
The real reasons—loneliness, healthcare anxiety, linguistic defeat, isolation masked as independence, financial strain—are harder to admit because they feel like personal failures rather than structural realities.
They’re not personal failures. They’re predictable outcomes of specific circumstances that affect single older women more than other demographics. Understanding them as structural rather than personal is the first step toward either avoiding them or accepting them as valid reasons to choose differently.
Who Does Succeed
Not all American women over 55 leave. Some thrive spectacularly. They share common characteristics:
Existing Portuguese connections: Women who move for marriage, established friendships, or to be near family members already in Portugal have built-in social support. The lonely bootstrapping phase is shortened or eliminated.
Exceptional language aptitude or prior romance language experience: Women who spoke Spanish, Italian, or French find Portuguese more accessible. Women with above-average language learning ability reach functional fluency.
Financial abundance: Women with generous budgets can hire help, pay for English-speaking services, travel frequently to visit US-based friends and family, and generally purchase solutions to problems that undercapitalized expats must suffer through.
Introversion or genuine comfort with solitude: Some women don’t need deep social connection. They came for climate, beauty, and peace. They got it. They’re content in ways that extroverted women cannot replicate.
Prior international living experience: Women who’ve lived abroad before know what to expect. The adjustment period doesn’t surprise them. The loneliness doesn’t panic them. They’ve survived it before.
Strong virtual community: Women who maintain deep friendships through video calls, who have American friends willing to talk daily, who supplement in-person Portuguese life with rich online connection, manage better.
What Would Need to Change

The high departure rate isn’t inevitable. It’s a product of specific circumstances that could theoretically change:
Expat communities could deepen. If established expats committed to building genuine relationships with newcomers rather than just introducing them to more newcomers, integration would improve. This requires established expats to sacrifice convenience for community.
Portuguese language instruction could improve. Classes designed specifically for older learners, with realistic timelines and practical rather than academic goals, would help. Most instruction follows models designed for younger students.
Healthcare navigation support could exist. A service that specifically helps foreign women establish medical care in Portugal—translating records, finding English-speaking providers, explaining medication differences—would reduce one of the major anxiety sources.
Financial planning could get realistic. Relocation consultants could provide single-woman-specific budgets rather than averaged data. Managing expectations before arrival prevents disappointment after.
But none of these changes are coming soon. The Portuguese government has deprioritized foreign retirement visas. The expat community is too transient to build lasting institutions. Language acquisition limitations are biological.
The Decision Framework
If you’re an American woman over 55 considering Portugal, here’s an honest assessment framework:
Go if:
- You have existing connections in Portugal
- You have abundant financial resources (30%+ above “comfortable couple” budget)
- You have prior success learning languages as an adult
- You genuinely prefer solitude to social connection
- You have strong virtual relationships that will continue
- You’ve lived abroad successfully before
Reconsider if:
- Your social wellbeing depends on deep in-person friendships
- Your budget is calculated to be “just enough”
- You’ve struggled with languages in the past
- You’re using the move to escape problems rather than pursue opportunities
- Your health requires complex ongoing management
- This is your first experience living outside the US
Test first regardless: Spend 3-6 months in Portugal before committing. Not as a tourist—as a trial resident. Rent an apartment, shop at local stores, attempt the bureaucracy, feel the loneliness, try the language. If you can survive the trial period with clear eyes about what it’s actually like, you’ll be better equipped to decide.
The Conclusion Nobody Wants

Portugal is wonderful. The weather is beautiful. The food is delicious. The healthcare system, once you access it, is genuinely good. The pace of life is humane. The people are warm.
And American women over 55 leave at disproportionate rates anyway.
Both things are true. The country can be wonderful and still be wrong for you. The decision to leave isn’t failure—it’s information processed and acted upon.
The 61% who leave aren’t weak or unprepared. Many were prepared by standards that turned out not to apply to their specific situation. They encountered challenges that affect solo older women more intensely than other demographics and made rational decisions based on their actual experience rather than their hoped-for experience.
Understanding why they leave isn’t meant to discourage the next woman considering Portugal. It’s meant to ensure she considers Portugal with open eyes rather than sunset-filtered Instagram dreams.
Some women will read this, move anyway, and thrive. Some will read this, move anyway, and leave in 18 months. Some will read this and choose not to go and never know whether that was the right decision.
That uncertainty is irreducible. What’s reducible is the surprise when things don’t work out. At least now you know: if Portugal doesn’t work for you as a woman over 55 arriving alone, you’re in significant company. The most prepared women sometimes leave too.
And that’s information worth having before you pack.
Leaving Portugal after eighteen months does not mean failure. It often reflects a mismatch between expectations and lived experience. Many women discover that their needs evolve faster than anticipated.
Successful long-term relocation requires emotional resilience as much as financial planning. Adjusting to slower systems, cultural differences, and language barriers takes patience and self-awareness.
Portugal remains an excellent destination for many retirees and remote workers. However, it is not universally suitable. Recognizing personal priorities is essential before committing.
Ultimately, long-term happiness abroad comes from realistic preparation, strong support systems, and adaptability. Those who thrive in Portugal are usually those who treat relocation as a long-term process rather than a permanent vacation.
About the Author: Ruben, co-founder of Gamintraveler.com since 2014, is a seasoned traveler from Spain who has explored over 100 countries since 2009. Known for his extensive travel adventures across South America, Europe, the US, Australia, New Zealand, Asia, and Africa, Ruben combines his passion for adventurous yet sustainable living with his love for cycling, highlighted by his remarkable 5-month bicycle journey from Spain to Norway. He currently resides in Spain, where he continues sharing his travel experiences with his partner, Rachel, and their son, Han.

Single, middle-aged female living in Portugal for more than 4 years
Saturday 3rd of January 2026
So, an article about single, middle-aged women in Portugal, written with made up numbers by a partnered, younger male who doesn’t live in Portugal. Gotta love it.
I know more couples who have moved on than single females. And there’s no same story about single males because so few have the guts to do it on their own (I’ve met 3 single men in Porto and 2 got into serious relationships with Portuguese women within a few months of arrival). While some of these issues we face are valid, they’re valid for EVERYONE, regardless of gender or marital status. And the money thing? We have to pay for everything no matter where we live so that’s not really a factor. It’s still cheaper to live in Portugal alone than to live in many places in the U.S. alone.
Living abroad anywhere has challenges. It’s not for everyone. This article makes it seem like people are failing by deciding that this life or location isn’t working. Don’t let this article scare you from trying if that’s your dream.
Solo female in Portugal - 4th Transcontinental Move
Tuesday 6th of January 2026
@Single, middle-aged female living in Portugal for more than 4 years, I know, makes me chuckle too :-)...young man from Spain (thanks :-)! I DO appreciate the article... solo singles don't get referred to, too often. Particularly women. I have met two single men 55+ who have moved here - in the three years since I have moved.
This is my 4th transcontinental move in 40 years. I know the ups and downs connected with acculturation and give it 5 years before really knowing how the place is for me.
I broke my ankle in 2 places 6 months ago and was holed up in my apartment for 4 of those. Nothing like the s*&% hitting the fan to see where you truly landed. I'm grateful to be here. While it's truly uncomfortable to navigate the health system - especially in time of need - it is also a big part of what is helping me acculturate.
Portugal is a relational society vs US which is transactional. I insist on continuing to use my limited Portuguese in daily life, even when the local will ask "do you speak English". I answer: "Sim, mais queria falar em Portuguese"...this changes the dynamic instantly and the quality of interaction deepens.
The loneliness factor is part of life anywhere and older adults face this more and more. Which is why one of the biggest investments one can make is to befriend oneself. You take yourself with you, wherever you go :-)!
Tomás
Saturday 3rd of January 2026
My wife and I moved here on retirement, and have never considered ourselves "expats." We're immigrants.
One thing the article didn't mention was how friendly and helpful the Portuguese people are. Examples:
Just yesterday, I was nerding out on getting a picture of my wife's plane flying over as she left to visit a friend in a nearby country. A gentleman who was walking by saw me, and started to talk to me in rapid Portuguese. I asked him if he spoke English, and in response, he walked the equivalent of a short block around and up on the platform on which I was standing, and proceeded to tell me how I could get a much better image from the roof of a nearby parking garage, sharing examples with me on his phone - all in Portuguese. As I understood him, I used my limited Portuguese to say so, and to thank him.
Merchants in our neighborhood wave as we pass, and some step outside to shake hands and exchange greetings.
As I waited one day for a Metro, an older man approached, crossing the tracks, and extended his hand to me to get a little help stepping up on the elevated platform. Little kindnesses like this are expected here, and we love that.
Peggy Bendel
Saturday 3rd of January 2026
Very helpful article! I moved to Portugal in February 2023 with my Portuguese-speaking husband (he was raised in Brazil of an American Mother and a Norwegian Father). Sadly, he died in his sleep just 7 weeks after our move, and I did think of returning to the US.
But we had found a wonderful apartment, made a few friends, and perhaps most importantly, solved the health care issue, thanks to a service called Serenity.
We contracted with them before we moved and had a Zoom meeting and follow-up communications outlining the various specialties we would need. Serenity recommended three physicians for each, based on their credentials and proximity to our home. When he died, they canceled all of his up coming appointments and our account executive asked if there would be funeral services in Portugal, since she would like to attend.
I have found the private health care here far superior to the US system, which is so fragmented and for-profit that then Bob had kidney stones removed the year before we emigrated, his surgeon couldn't access our PCP's portal and vice versa.
There are also many services available that can help with repairs/handyman tasks at a reasonable price.
Making friends is challenging everywhere,cespecially as we age (I am 82), and it's important to be proactive: joining clubs and other activities, even if restricted to other costs at the beginning.
It is true about Portuguese being very family-centered and multi-generational. They also may have smaller apartments and be reluctant to host people perceived as more affluent.
They also will ALWAYS apologize for their English, which is far better than my Portuguese will ever be. They are so appreciative of every attempt to master even simple phrases of their admittedly challenging language! The government provides a free school year of 2x week classes, too.
I am closer to my NY state-based brother and extended family here, via nonstop from Lisbon than when I lived in Arizona, a minimum of two flights away. I have welcomed many friends and family here, too!
WhatsApp is an invaluable tool for staying in touch with family and friends in any part of the world. Video calls with many, high-quality voice calls, too. Internet/TV/cell plans are MUCH cheaper than anywhere I have ever lived, with several providers to choose from.
Finally, Cascais is truly beautiful...but it is also the most expensive place to live in Portugal. I live about 45 minutes south of Lisbon, with excellent public transportation and no need for a car.
Portugal is home now, and I bless my late husband every day for initiating our move. I hope others will be as happy in this wonderful country (and we haven't even touched upon the food and wine...)!
Gaby Wehle
Friday 9th of January 2026
@Peggy Bendel, Hi Peggy! Wishing you a fabulous New Year. I just saw your wonderful feedback—thank you so much! It’s been too long since we met, and I'm sorry we fell out of touch. Hopefully, our paths cross again soon. Best, Gaby.
Teri
Sunday 4th of January 2026
@Peggy Bendel,
Jill
Sunday 4th of January 2026
@Peggy Bendel, beautifully written, so much grace. Thank you.
I'm so sorry for your loss. Loving kindness to you. Fique Bem.
Mary
Saturday 3rd of January 2026
Terrific well rounded article that I wish to add to as an older woman. Anyone can be lonely anywhere. Travel can be affirming and challenging but travel for a single older woman has the burden of including social prejudice against older single people especially if their gender is female.
Carmen c
Monday 5th of January 2026
@Jill, wait, there are single men here? Geez.
Jill
Sunday 4th of January 2026
@Mary, so true. Single women make so many people uncomfortable. They either worry we are after their husband or want to fix us up with single men they know.
Big Gonads
Friday 2nd of January 2026
Ask Why Men Over 55 Rarely Move to Portugal Alone It’s simple: they don’t. Unlike women who boldly grab a one-way ticket and dive into the bureaucracy, most men can’t handle the idea of navigating bureaucracy, loneliness, or cooking for themselves. Portugal is beautiful, challenging, and full of opportunity — but apparently, the thought of doing it without someone holding their hand is terrifying. So they stay home, play golf, and pretend retirement abroad is “too complicated.”