By Meghan Streit, KiplingerMore Americans are leaving the country to live out their golden years. Here’s how to embark on an international retirement.

Senior couple embracing on beach, rear view © Digital Vision, Digital Vision, Getty Images

In 2001, Terry Leary and her sister, Nancy Bergman, were traveling in Nicaragua. They stopped for a few nights in Granada and were so enchanted with the quaint lakeside town that they decided they’d like to live there permanently. Within a week, Leary, 65, and Bergman, 69, purchased a property in Granada with plans to open a small hotel. “I had always said that someday I wanted to run a B&B in Latin America,” Leary says.

After a year and a half of renovations, Leary realized that dream. She and Bergman opened the doors to Hotel Casa San Francisco, a boutique hotel with a tapas bar in the heart of Granada’s historic district.

Leary and Bergman, natives of San Francisco, worked in various places across the globe before relocating to Granada. Leary spent her career as an independent contractor for the U.S. Agency for International Development and continues to do consulting work for the organization. Bergman was formerly a flight attendant. She also previously worked as a real estate agent and continues to sell real estate in Nicaragua.

Leary acknowledges the common perception that opening a business in Latin America brings with it a certain amount of “red tape.” She says finding trusted local business advisers and learning the language are two keys to success. “Everybody talks about bureaucracy in these other countries, but our bureaucracy in the U.S. is so much worse,” Leary says. “You just have to find somebody who knows the system to help you.”

Lured by warm climates, beautiful scenery and lower cost of living, an increasing number of older Americans are opting to retire abroad. And just like many retirees in the U.S., a large number of expats are continuing to work, says Betsy Burlingame, founder of Expat Exchange, a website with resources for Americans living overseas. Of the baby boom generation, Burlingame says, “a desire to push boundaries and explore new frontiers has always been a hallmark of this group, which is now retiring in large numbers.”

As with their stateside counterparts, some overseas encore careerists work because they need the money, while others desire to explore a new field. Burlingame points expat work-seekers to her site’s international jobs section and the site’s message boards, where they can connect with Americans already living abroad.

Before you move to a country, you should find out how difficult it will be to obtain a work permit — and whether you can even get one. Also check out how tax liabilities will be handled.

People who want to live overseas but need to earn money have to be creative. Retired dentists and physicians sometimes open small practices in their new locales. Some people are able to telecommute or consult for their former U.S.-based employers with nothing more than a laptop and an Internet connection. Financial advisers and accountants can create businesses helping other expats organize their financial lives. “Retirees often find jobs teaching English, working at hotels and giving tours to English-speaking travelers,” Burlingame says.

Open a business overseas

Retirement also can be an ideal time to start a business. Maybe you’ve always dreamed of running a yoga studio or opening a coffee shop. “In some cases, starting a business that employs locals may be an easier route than finding a job because it’s seen as an investment in the country,” she says.

Retired Americans hoping to launch a business may find some foreign cities more ripe with opportunities than in the U.S. David English, author of Expat Entrepreneurs in Argentina: Ten Success Stories, says that some Central and South American countries don’t yet have many of the products and services available in the U.S., and savvy entrepreneurs can fill those gaps for consumers. “You can take a risk because far less capital is required than in a mature market, so the U.S. dollar can go a lot further,” he says.

As wine lovers, Tom Phelan, 72, and his wife, Yvonne, 69, had often fantasized about buying a vineyard when they retired from their real estate careers in Phoenix, Ariz. But when they started researching options in California’s wine country, it seemed they couldn’t afford to finance their dream. “When we got ready to semi-retire seven years ago, we started seriously thinking about it, but land in Napa and Sonoma was $300,000 an acre,” says Tom Phelan.

Then, on a business trip in Argentina, Phelan discovered he could purchase a sprawling piece of land for a fraction of that cost. For just $132,000, the Phelans bought 108 raw acres in San Rafael in 2007. Tom and Yvonne moved from Phoenix to San Rafael to oversee the development of what would become La Vida Buena Vineyard.

Once their vineyard was up and running, the Phelans encountered other Americans interested in following in their footsteps. So they started selling off developed plots of land to other would-be winemakers. Their website, Argentine Vineyards for Sale, gets 13,000 hits a month, Phelan says. “Our goal is to sell enough vineyards so that we can build a house on the land and keep one vineyard for ourselves,” he says.

Phelan says Americans should be extra cautious to avoid scams and unfavorable business deals, especially if they don’t speak the native language. “Far too many people come to a foreign country and want to believe whatever they want to do, like open a restaurant or a bodega, is a piece of cake,” he says.

Phelan assembled a team of local experts, including a lawyer, an accountant and a land surveyor. His wife speaks fluent Spanish, which Phelan says was invaluable in dealing with advisers and workers in Argentina. His advice for expat entrepreneurs: “Don’t pay up front, and get everything in writing.”

Phelan also recommends renting an apartment and spending a month or more in a country before buying a home there. “If you visit a place for three or four days, you are a vacationer,” he says. “But after four or five weeks, you will be able to see if you like the area, the food, the culture and the people.”

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