Twenty years ago, when I first visited Málaga, it was the ugly stepsister of Spain’s Costa del Sol: a little scruffy and down-at-heels (though with gloriously sunny weather and a seaside location). So it was pure pleasure to return last summer and find it transformed into a Cinderella: one of Spain’s most livable—and affordable—cities for coastal living. Today’s Málaga is clean and bright, with a pedestrian-only city center and a revamped harbor area that is a joy to stroll. The city is brimming with museums, great dining, and plenty of shopping to suit all tastes and budgets.

When it comes to the ideal beach lifestyle abroad, many expats look to Koh Samui, in southern Thailand, where the palm-lined beaches, azure ocean, year-round tropical weather, and affordable costs make for ultra-easy living. Just an hour-and-a-half flight from the Thai capital of Bangkok, Koh Samui offers something for everyone, whether you dream of a tranquil seaside retreat or prefer frequent nights out on the town.

In Ecuador, you’ll not only be in the middle of the world, but you could be on top of it. That’s because thanks to its location on the equatorial “bulge,” the peak of the country’s 20,564-foot Mt. Chimborazo is the point on the Earth’s surface that’s the farthest from the Earth’s core and closest to the sun. There truly is something for everyone here. Mountains, beaches, rainforests, cities, and small towns…all with a price tag nearly anyone can afford. By the way, Ecuador’s currency is the U.S. dollar—no currency conversions necessary.

"The developer here is in jail…” is something I heard a lot. It was alarming…but in a way, it was reassuring, too. Puerto Vallarta—one of Mexico’s most popular expat destinations— is home to an estimated 10,000 North Americans living here full-time. They chose Puerto Vallarta for good reasons. Puerto Vallarta sits at the foot of the grand Sierra Madre mountains that sweep down to the Bay of Banderas. It’s a warm and sunny spot with tropical beaches, fresh ocean breezes, and temperatures that average 73° F to 83° F all year.

I walked into the main Credit Suisse branch in Chicago and told the doorman I wanted to open a Swiss bank account. I was led to a private office overlooking the Chicago skyline. Was asked for my minimum deposit. Being just 31 at the time, I played it conservative and started with just $2,000 (about $4,300 in today’s dollars).

The bidding in the auction room stood at 2 million Hong Kong dollars—and all eyes were on me. Ceiling fans offered some respite from the stifling heat outside, but the room still seemed unbearably hot. Some 40 or 50 collectors and dealers, many of whom had made the trip from mainland China, jostled for elbow room. A bank of auction assistants manned telephones and laptops, processing bids from around the world.

For Olley Ollerenshaw, living in Cusco’s historic artisan district of San Blas has allowed a childhood fantasy to come true. “I’ve always been interested in maps of the world, maps of all kinds. Maps are symbols of adventure as well as functional tools, and for anyone like me who grew up daydreaming about visiting exotic places, maps hold a special allure,” says Olley.

Before moving to Italy, Georgette Jupe had what many would consider a glamorous life: She was living in star-studded Los Angeles, working in public relations, and rubbing elbows with the B-list celebrities that her firm represented. She had a good, steady, lucrative job. And who doesn’t want to live in sunny, coveted southern California? To the untrained eye, Georgette had it all. But secretly, she was missing Italy— where she’d spent one beautiful year studying abroad in pretty Florence back in her college days.

I’ve never seen so much green...and in so many shades and variations. The tall, jungle-covered mountains of Costa Rica’s Southern Zone dominate the landscape. And many locals and long-time expats say they enjoy these mountain views even more than the ocean, thanks to the lush vegetation that covers them. This region, on the southern Pacific coast, is a land of extremes. Empty beaches, wild Pacific waters, those tall mountains dropping to brief lowlands before turning to a strip of sand, and then blue ocean.

No matter how affordable the destinations we talk about are, the simple fact is: You can’t live anywhere for free… But what if you had an income that went with you? An income that could give you the freedom you need to just pick up and go? You could spend half the year in your own cottage on the beach…work in the mornings and snorkel and relax in the afternoons.