When I was five years old, my parents moved us overseas. That first relocation led to seven more—Austria, Japan, Mexico, Canada, Peru—and eventually to a life where I’ve traveled to more than 80 countries. For me, “home” was always shifting, and that early experience taught me something my clients often discover later in life: living abroad isn’t just a postcard dream; it changes how you manage money, health, and even family legacies.
Today, I’m hearing the same question over and over: “What would it look like if I retired abroad?” And it’s not just curiosity. More than 760,000 Americans receive their Social Security benefits overseas. Furthermore, nearly half of Americans have seriously considered retiring abroad.
Here are the three areas I discuss with clients, plus resources I use to make these conversations real.
Key Takeaways
- More than 760,000 Americans already receive their Social Security benefits overseas, and nearly half have considered retiring abroad.
- Clients can compare their current expenses with their dream destination using online tools to calculate cost-of-living differences across cities.
- Tax treaties and residency rules vary across countries, so research is vital before making big decisions.
- Medicare doesn’t cover care abroad, so securing private or local health insurance is essential for retirees overseas.
- Estate and inheritance laws differ by country and can override U.S. wills, making cross-border estate planning crucial.
1. Money and Cash Flow
A tourist can live out of a suitcase. A retiree needs a plan. I encourage clients to compare their current expenses with their dream destination using resources like Numbeo or Expatistan, which calculates the cost of living differences across cities.
Client Example
One of my Latin American clients living in Miami wanted to move to Spain. Madrid looked appealing not just for culture, but also because the cost of living was about 30% lower than Miami’s. By opening a euro account and diversifying his investments, he insulated himself from currency swings and could enjoy extra perks like more travel without worrying about the exchange rate.
2. Legal Rights and Taxes
Residency rules, visas, and tax treaties must be considered well before your tourist visa expires. I often guide clients to the IRS tax treaty list and the Social Security Administration’s international programs to confirm benefits and obligations.
Important
The U.S. imposes taxes on its citizens living abroad. Eritera is another country that implements a form of citizen-based taxation.
Client Example
One of my clients moving from the Caribbean to Latin America faced an unexpected challenge: a wealth tax on citizenship. We restructured her accounts before the move so she could minimize double taxation. It wasn’t the kind of planning she initially thought about, but it saved her thousands.
Important
These decisions are case-by-case and should often be consulted with local attorneys.
3. Healthcare, Estate, and Well-Being
Money is important, but health and peace of mind matter just as much. Medicare generally doesn’t cover care outside the United States, so retirees must secure private or local insurance.
Estate plans also need adjusting—civil law countries often enforce inheritance rules that can override U.S. wills, as highlighted by organizations like STEP.
Client Example
A couple who moved to Thailand loved the lower healthcare costs but were surprised by restrictions on property ownership. Renting, instead of buying, and updating their wills gave them flexibility and legal protection while still allowing them to live the lifestyle they dreamed of.
The Bottom Line
Retiring abroad isn’t just about chasing sunsets. It’s about ensuring that cash flow, legal rights, and healthcare are aligned so clients can enjoy the next chapter. Yes, they can research independently, but I’ve seen how costly DIY mistakes can be, from double taxation to estate disputes.
I still remember my parents’ first international move—boxes piled high, new languages to learn, and the uncertainty of the unknown. That memory reminds me why I guide clients through this process today: with the right planning, what feels overwhelming can become a new definition of freedom.
