Key Considerations Before You Move

Choosing a country is only the first step. The real work involves a deep dive into the practicalities that will shape your daily life. An affordable retirement abroad is possible, but only with clear-eyed planning. Here are the most critical factors to consider, no matter which destination you are exploring.

Healthcare Is Paramount

This cannot be overstated: U.S. Medicare does not cover you overseas. You must have a plan for healthcare. This will mean either purchasing a comprehensive international private health insurance policy or, once you are a legal resident, joining the national healthcare system of your new country. Many expats do both. It is also wise to consider medical evacuation insurance. This special policy would cover the high cost of transporting you back to the U.S. in a major medical emergency. Before you move, get a full physical, see your dentist, and get extra pairs of glasses. You can find official information on this topic at government websites like Medicare.gov.

Taxes and Finances

As a U.S. citizen, you are required to file a U.S. federal tax return every year, regardless of where you live. This does not necessarily mean you will owe taxes, as there are provisions like the Foreign Tax Credit, but the filing obligation remains. Your Social Security benefits will be sent to you abroad, which you can learn about on the Social Security Administration’s website at www.ssa.gov. Managing your finances across two countries involves some complexity. You will need to figure out the best way to transfer money, open a local bank account, and understand your tax obligations in your host country. It is highly recommended to consult with a tax professional who specializes in expat issues before you make any decisions.

Staying Connected with Family

The emotional side of moving abroad is just as important as the financial side. Think realistically about the distance. Missing weddings, birthdays, and the everyday moments with grandchildren can be difficult. Factor the cost and time of travel back to the U.S. into your budget and your emotional bandwidth. While video calls are a wonderful tool, they are not a substitute for a hug. Have open and honest conversations with your family about your plans and how you will all work to stay connected across the miles.

The “Try Before You Buy” Rule

The single most important piece of advice from successful expat retirees is this: do not sell everything and move permanently based on a one-week vacation. Plan an extended “test drive” visit of at least three to six months. Crucially, try to do this during the country’s “worst” season—the rainy season in Costa Rica or the cooler, damp winter in Portugal. Rent a home in a neighborhood you are considering, not a tourist hotel. Go grocery shopping, visit a doctor for a checkup, try to pay a utility bill, and navigate public transportation. This experience will give you a true taste of daily life and help you make a much more informed decision. The goal is to move from being a tourist to a temporary local. This simple step can save you from a costly and heartbreaking mistake.