As the saying goes, the grass is greener on the other side—especially now, as a changing America prompts even more boomers to explore life abroad.
A 2024 Expatsi survey of over 116,000 Americans who wanted to leave the country showed that two-thirds plan to move abroad by 2026, while 30% of those surveyed were looking to retire abroad. Among the top reasons cited were a desire for new experiences, rising U.S. conservatism and affordability concerns.
Golden Harbours, a company providing international living solutions, noticed a 420% spike in its website traffic compared to pre-election time.
“After the most recent USA elections, we observed a significant upward trend of inquiries, people looking for a backup plan solution,” says Sergey Voinich, founder of Golden Harbours.
Moving abroad—especially for those in or nearing retirement—is a big decision. While it appeals to many, it’s not for everyone. In this article, we’ll trade real stories and expert advice to help you decide whether to move abroad or simply take an extended trip.
Dreaming of Paris
The first time Janice Deerwester visited France in the late 1980s, she somehow knew she wanted to live there. “I couldn’t tell you why then,” she said. “I loved the old architecture and the history.”
Nearly four decades on, at 70, she journeyed to Paris—only now, it was for a longer stay.
Now based in Fountainebleau, a town southeast of Paris, Deerwester is a well-known face in the Francophile community on YouTube. Her channel Janice in France, where she shares her everyday life abroad, has over 33,000 followers.
“My YouTube channel is not to inspire people to move to France,” she explains. “It’s to inspire people to live and do what they want to do while they can.” She also reveals she’s been working on a book.
Deerwester describes her first days in France as depressing. “It was almost like my brain hadn’t caught up to my body yet,” she explains, but a trip to IKEA and some personal touches helped. She says it helps having familiar items around, like family photos, which can make a new place feel like home.
Although she is now living la vie en rose, Deerwester acknowledges that expat life in France “is not for the faint of heart” and there were things she could’ve done differently.
“I wish I had used the nine months before I moved to learn French,” she says. A lover of the language, she aspires to speak French in full sentences one day. She also would have engaged an immigration attorney to help with the process instead of managing things on her own.
Starting Over in Italy
About 1,000 kilometers from Deerwester, in the land of pizzas and opera, Chris Sobolev and her husband Pete are thriving in their 60s. Not only did this American duo adjust to life in a foreign land, they built communities along the way.
Italy wasn’t a retirement plan for the couple, but an opportunity to reboot their marriage. With their kids grown, they craved a new chapter where they could work as a team again.
Sobolev had been a real estate professional in California, and quickly put her skills to work in Italy buying and renovating abandoned homes. The Calabria-based couple made their first purchase in Santa Domenica Talao 15 years ago. Today, they guide other foreigners to their Italian dream homes.
“Ultimately we started Super Savvy Travelers, our Italian property consulting business, really as a way to give back to the people of Santa Domenica Talao who had welcomed us so beautifully and warmly,” she says. The couple’s business has brought many investors to the area.
Life here seems great for the couple, but not without pet peeves. For example, the infamous Italian bureaucracy can turn simple tasks, like getting a driver’s license, into a slog.
Accessibility is also an issue. For Sobolev, who had a failed hip replacement, getting around could be challenging in Italian hill towns, notorious for steep slopes and narrow pathways. After mobility issues developed, the couple moved to a house with more uniform and manageable interior stairs. Because accessibility affects mobility, Sobolev suggests thinking long-term when purchasing a residence.
A dream home, however, doesn’t carry the whole relocation plan. She and her husband also made an effort to network and make friends. While they have integrated well, she acknowledges that not everyone finds it as easy, especially without fluency or local ties.
“A beautiful farmhouse in the country sounds amazing for a couple but can be cripplingly lonely for someone alone who has not learned the language and has not built up a network of good friends,” says Sobolev. “Building a community or joining one that already exists is my best advice to anyone coming over.”
Common Blind Spots for Would-be Expats
Experts warn many retirees underestimate the challenges of moving abroad, but planning can prevent costly mistakes. Here are some things to think about.
Financial Risks
“Many Americans assume physical residency and tax residency are the same, but in most countries they’re distinct,” says Amy Short, principal of Golden Visa Direct, a company that helps Americans obtain residency in Portugal. As a U.S. citizen, you must file U.S. taxes even if you live overseas; hence the need to keep in mind cross-border tax planning.
Estate planning is another factor to consider, as intestacy laws in Europe vary greatly and U.S. trusts or wills aren’t recognized in most places, says Short.
Let’s say you were a U.S. citizen with assets in France. The local inheritance law might force the passing of 50% of your assets to your spouse or children, even if your will says otherwise.
Currency fluctuations also pose a risk. Clément Maignen, co-founder of Devyzz, says unfavorable exchange rates and hidden fees can cost remitters up to 5% per transfer.
“If you’re transferring $30k/year over 10 years, that could be up to $15k lost to your bank in transfer costs,” says Maignen.
Therefore, he suggests using forward contracts, a tool to secure future foreign exchange rate, or rate alerts to optimize transaction timing.
Health Care Risks
A common misconception among Americans is that Medicare can be used globally—which is inaccurate. Expats needing advanced care might need to return home or purchase international insurance, which can put strains on their finances. (Your new home country may offer permanent residents access to a national health insurance system but there could be eligibility requirements, additional fees or limits on services.)
International health insurance is essential for accessing quality care abroad and is usually cheaper than full U.S. health insurance, says Insured Nomads’s CEO Andrew Jernigan. However, it’s still a major cost that many neglect to include in their relocation budget.
Though not always required for visas, international health coverage becomes crucial if medical issues arise.
Property Investment Issues
Given how prohibitively costly the U.S. housing market is, many Americans rush into what look like bargains.
“I’ve seen it time and time again, where an expat purchases a home in a small town, only to realize later that it’s much more difficult than they had anticipated,” says Sarah Pardi of Insurte, pointing to challenges like language barriers, limited access to essentials, and narrower social circles.
Political stability and overall safety are also important considerations. You’ll be hard-pressed to find cheap paradises without downsides.
It’s common for relocating Americans to rush into major transactions without considering legal and fiscal precautions, says Casey Halloran, CEO of Costa Rican Vacations.“The enthusiasm to be abroad sometimes leads to being too trusting or taking risks that they would never do back home.”
The rule of thumb, he says, is to rent for at least one year before making any permanent decisions regarding a home.
Visa Issues
Some Americans may be unaware of just how specific visa rules can be.
In some countries, the wrong visa can jeopardize your legal status, so it’s crucial to get the right visa in order. For instance, Spain’s Non-Lucrative Visa grants a one-year stay but prohibits all work. Those seeking income are better off with the Digital Nomad Visa.
Depending on the country and submission status, the visa or residency process often takes two to 12 months to complete, says Voinich. However, backlogs and delays may hinder processing time.
Social Issues
Every move abroad starts with a honeymoon phase—until reality sets in, bringing common struggles like homesickness and language barriers will surface.
To survive this phase, it’s essential to do proper inner work and build emotional resilience, says
Lisa La Valle, a career coach at Expat Whisperer who spent seven years in Europe.
“You are going to spend a lot of time alone,” she says, so you need to be emotionally prepared to live among people who communicate and do things differently. An intercultural trainer, she says, can help recalibrate your expectations and ease your transition.
Popular Destinations Among American Expats
Despite these caveats, many Americans desire to live abroad. Here are some of the most popular places to retire, as highlighted by International Living and Golden Harbors:
- Mexico: Close to the U.S. with well-established expat hubs. Cost of living is approximately 60% lower than the U.S.
- Costa Rica: Popular for its political stability, lush landscapes, and affordable private healthcare
- Argentina: Offers budget-friendly living, a vibrant expat community, and a straightforward visa path for retirees
- Uruguay: Known for beautiful beaches and a stable economy. Offers retiree-friendly residency options and affordable healthcare plans.
- Portugal: The D7 Visa suits budget-conscious retirees, while the Golden Visa offers a route to EU citizenship and long-term benefits.
Photo by sirtravelalot/Shutterstock.
