When it comes time to flip the switch to retirement, we hope to have organized our lives so that we're able to move around during that stage among a handful of destinations where we most enjoy spending time, with established infrastructure in each so that we can come and go as residents, not tourists, with friends and connections, social circles and—important to us—homes of our own.

When making your own plan for spending at least some of your retirement overseas, the starting point, key to the success of the adventure, is to be honest with yourself about what kind of lifestyle you're after. When we ask ourselves what kind of life we want in retirement, the answer is: varied. City and coastal, Caribbean and highland, spring and summer, fall and winter, developed and emerging, sophisticated and raw, refined and gritty, we appreciate it all. So we've conceived a retirement strategy, which we've been working for more than 20 years to engineer, that will allow us to enjoy it all, perpetually, in turns. We've held on to the apartment in Paris that we called home when we lived in that city with our children. This will be our co-retirement base, along with the beach house we've built on the Pacific coast of Panama, meaning we'll be able to reposition ourselves regularly between the Old World and the New. This might seem like an ambitious plan, but we've had time to evolve it.

Whatever your intentions, start developing the plan. An easy first step can be the purchase of a piece of property in a locale where you want to be able to spend time now and that you think eventually could become part of your retirement plan. Meantime, whenever you're not using the property yourself, it could be generating cash flow from rental, and, over time, it could be increasing in value, too. Your future retirement residence could be a nicely income-generating and appreciating asset on your balance sheet. Indeed, that's the ideal situation—when the holiday home-cum-retirement plan you buy also qualifies as a cash-flow investment.

That's why, when sizing up the global marketplace and the world map for potential cash-flow opportunities, a short-term rental property can be the place to start.