Trent Anderson may drive for Uber in Tampa, Florida, but his daydreams take him to places like picturesque Malaga, a city in the south of Spain.
"It's got the beach. It's got the mountains. It has a big-city feel, but it's not that big," said Anderson, 49.
The dream was inspired by a recent trip through Portugal and Spain in March which gave travelers a taste of daily life across the Atlantic. It was organized by Expatsi, a firm which helps Americans intrigued by the idea of living abroad.
"When we started thinking about moving abroad ourselves, we built all these massive spreadsheets of data about different countries," said Jen Barnett, an Alabama native who founded Expatsi with her husband Brett Andrews.
Figuring other people might be able to use that information, the couple, who recently moved to Merida in Mexico's Yucatan, launched the business to match expat wannabes with their dream destinations.
On their website, a 20-question survey starts with "Why do you want to move abroad?"
Relocating overseas is a big leap, but many have already done it: At least 5.4 million Americans lived abroad in 2023, according to the Association of Americans Resident Overseas.
The strong U.S. dollar is a very good incentive. Since most Americans are far behind on retirement savings, moving to a place with much lower living costs immediately boosts their standard of living.
Costa Rica is the best place to retire, according to International Living magazine's 2024 Global Retirement Index ranking locales based on various criteria. Portugal, Mexico, Panama and Spain round out the top five.
For those who want a trial run, an Expatsi trip to Spain and Portugal is set for September, followed by France and Italy in October, and Mexico on the horizon.
Here are some tips for those who are scouting abroad for their retirement years:
DO NOT BE A TOURIST
Stay in homes on Airbnb or VRBO in residential neighborhoods, Barnett suggested. Staying in hotels on guided vacations with quick visits to tourist hotspots give no idea about what it is like to live in a place.
"What is it like day-to-day, going to the grocery store or pharmacy, visiting a clinic, taking public transportation?" Anderson said. "It's not about the museum."
RENT
Fantasizing about owning a place abroad is easy, but if the experience falls short you could be in a jam because it is much harder to sell a home than to buy one, Barnett said. It can tie up your assets and trigger unforeseen tax consequences.
That is why Barnett rents in Merida with her husband. They could easily move elsewhere.
DIG INTO RULES AND REGULATIONS
Figuring out the legal and financial ramifications of retiring abroad can take some fun out of a vacation, but it helps to make sure what you are getting into.
The Internal Revenue Service requires expats to file tax returns on income, gifts and inheritance in the same way as if they are living in the United States. Check out Publication 54, Uncle Sam's tax guide for Americans living abroad, here.
Visas for work, study or retirement can vary widely for each country. 'Golden Visa' programs make pathways to residence and citizenship easier for investors.
As for healthcare, a major concern for seniors, does your target country have universal coverage? Will you secure private coverage abroad or pay out of pocket?
To address these tough questions early, Expatsi trips kick off with a half-day seminar featuring several local experts.
"Just do it" if you are thinking about visiting a potential retirement location, said Anderson, the Uber driver, who is considering going on Expatsi's trip to Mexico.
"No amount of research can replace being there and experiencing it for yourself."
