"They Sold Everything, Bought a Backpack, and Now Live in a Different Country Every Month. Could You?"
Retirement Perspectives | June Edition
A story I recently read about highlighted a couple that did something most people only daydream about. In November 2022, they retired from their San Francisco tech careers, sold their home, gave away the furniture, donated most of their clothes, and hit the road — for good. Peru. South Korea. Romania. Living out of a single backpack and suitcase, moving every few weeks, with no mortgage, no lawn to mow, and no alarm clock.
They're not alone. A growing number of retirees are choosing what's become known as the "global nomad" lifestyle — full-time international travel with no fixed home base. And the people who've tried it tend to talk about it the way people talk about falling in love: with an almost evangelical fervor. In this article it highlighted another couple who did it for 12 straight years, visiting 95 countries before returning to Seattle in 2025.
What draws people to this life is different for everyone — the cost savings in some cases, the hunger for adventure in others, the pandemic-era reckoning about what actually matters. What keeps people going is harder to explain until you hear them try. After years on the road, many find they've found it.
The finances are more manageable than most people assume. One couple budgeted $5,000 a month and came in around $63,000 for 2024. Another couple aimed for $90 a night on lodging. A couple in Australia lives comfortably on $40,000 a year. For retirees fleeing expensive cities — and especially those willing to choose destinations wisely — the math can actually work better than staying home. Some nomads even generate income from travel blogs, YouTube channels, and membership communities they build along the way.
Healthcare is the biggest logistical hurdle, and it deserves serious planning. Standard Medicare doesn't cover care outside the United States. Some Medicare Advantage plans cover emergency care abroad, but coverage is limited. Most full-time nomads purchase global health insurance — companies like Cigna, Allianz, and AXA offer policies that cover international care including pre-existing conditions. One highlighted couple pay roughly $5,800 a year for $1 million in coverage for both of them outside the U.S. and several nomads note with some surprise that the quality of medical care they've received abroad — in Serbia, Thailand, Mexico — has been excellent, often at a fraction of American prices.
On the tax and logistics front: nomads still owe federal taxes on Social Security, investment income, and other sources. State tax obligations depend on where you claim domicile. Many nomads who no longer own property strategically establish domicile in a state with no income tax — South Dakota is a popular choice — which requires demonstrating a physical presence there, typically just one night and obtaining a driver's license. A virtual mailbox service handles physical mail digitally, typically for $120 to $200 a year. These are solvable problems, but they require a plan — and ideally a financial advisor who's thought through the details before you book the first flight.
Speaking of life after 65, what does turning 80 actually mean in 2026. Dolly Parton, Bill Clinton, George W. Bush, Cher, Sylvester Stallone, Steven Spielberg — they're all joining the octogenarian club this year, and they're redefining what that milestone looks like. Baby Boomers turning 80 are the wealthiest, best-educated older adults in American history, and they're not going quietly into the rocking chair. An 80-year-old man today can expect to live another eight-plus years on average; a woman, nearly ten. As Dolly Parton put it when asked about turning 80: "Well, so what? Look at all I've done in 80 years. I feel like I'm just getting started."
That said, the milestone deserves some real attention. If you haven't seen a geriatric specialist, now is the time — not because something is wrong, but because geriatricians are trained to look at the whole picture: physical health, cognitive health, medication interactions, and long-term planning in a way that a general practitioner simply doesn't have time for. Equally important: social connection. The research is unambiguous — loneliness and isolation are linked to higher rates of heart disease, depression, cognitive decline, and earlier death. Staying connected isn't a luxury in retirement. It's medicine.
And if you haven't updated your estate documents — wills, trusts, health proxies, power of attorney — in the last several years, I advise to do it now. Life changes. Tax law changes. Family situations change. What made sense a decade ago may no longer reflect your wishes or your reality.
For retirees who are self-employed — consulting, freelancing, running a small business — there's a significant tax deduction many are missing entirely. If you have self-employment income and are enrolled in Medicare, you can deduct your Medicare Part B, Part D, Medicare Advantage, and Medigap premiums directly from your self-employment income. This is an above-the-line deduction, meaning it reduces your adjusted gross income even if you take the standard deduction. Your spouse's Medicare premiums are deductible too. Long-term care insurance premiums are also deductible up to age-based limits — up to $4,960 for those between 61 and 70, and up to $6,200 for those 71 and older.
We have seen a client's accountant missing thousands of dollars in deductible Medicare premiums right before the return was filed. The error was avoidable. If you're self-employed in any capacity and haven't had this specific conversation with your tax preparer, it's worth having before you file.
On the health front, two findings to highlight: First, a study published in the journal Neurology found that older adults who received a high-dose flu vaccine — the version specifically recommended for people over 65 — showed meaningfully lower rates of Alzheimer's disease compared to those who received the standard dose. Researchers are now examining other common medications, including statins, shingles vaccines, hypertension drugs, and GLP-1 diabetes medications, all of which show promising associations with reduced dementia risk. The science is still evolving, but the signals are encouraging enough to discuss with your physician.
Second: scam awareness has never been more important. From 2020 to 2024, the number of older Americans who lost $100,000 or more to scams increased nearly sevenfold. The four most common schemes targeting retirees right now are investment fraud (often involving fake cryptocurrency accounts), government impersonation (fake IRS or Social Security calls), romance scams via social media, and tech support scams that hijack computer access. The IRS, Social Security Administration, and Medicare never initiate contact by phone, text, or email. If someone claiming to be from a government agency contacts you unexpectedly, hang up and verify independently before doing anything.
And finally — Europe may literally pay you to move there. Five European countries are actively offering financial incentives to attract new residents: Italy, Spain, Greece, Ireland, and Portugal. Italy's most compelling offer is a 7% flat income tax rate for up to 10 years for retirees who settle in certain southern regions — significant when Italian marginal rates can exceed 40%. Greece offers a similar 7% flat rate for up to 15 years. Ireland provides renovation grants of up to €70,000 for buyers who restore vacant homes. Portugal offers relocation grants of up to €6,000 for those moving to rural areas. And some small Italian towns literally sell houses for €1.
The catch, as always, is in the details — residency requirements, renovation timelines, visa prerequisites, and local versus national program eligibility all need careful review. But for retirees considering an international move anyway, these incentives can meaningfully offset the cost of starting over.
Retirement has never looked less like retirement. Whether you're dreaming of a backpack and a one-way ticket, optimizing a Medicare deduction you didn't know existed, or simply making sure your estate plan reflects who you've become — the best retirements are the ones that get planned, not just hoped for.
If any of this sparked a thought about your own retirement picture, let's talk. The conversation is always free.
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