City, Small Town, Beach, Or Mountain— Which Is Your Dream?

Because in the end, you won’t remember the time you spend working in the office or mowing your lawn. Climb that goddamn mountain. 

Out of this big old world of 195 countries, how in the world do you figure out where in the world to go?

If you’re just beginning to think about the idea of going overseas, whether for retirement or otherwise, this is a huge, daunting question.

Where do you start?

My favorite piece of advice for beginning to tackle this conundrum is to picture what you want to see when you wake up and pull back your curtains. What is outside that window? When you open your door to greet the new day, what is it that’s greeting you back?

One thing informing that panorama is climate. When you look out your bedroom window, are you looking at palm trees and sunshine? Streets powdered with snow? Flowers blooming against a backdrop of mountains and valleys? Does the scene change from month to month… or does the climate hold steady throughout the year?

This first consideration will help you narrow down the regions of the world you could be considering. Thinking very generally, you’re choosing from among three categories: tropical, temperate and seasonal, or mountainous.

Each of these options has its pros and cons.

Many, for example, start this retire-overseas thinking process thinking they want tropical. However, tropical can be a big adjustment for someone who’s never lived outside the Northern Hemisphere.

The length of daytime never changes, the temperature and humidity never waver… it’s all the same all year long. I had a hard time after a few years in Panama, because I missed the change in seasons and the different lifestyle opportunities that each season offers.

If you want some change throughout the year, don’t forget that extremity of seasons is customizable to your preference. Seasons bring a lovely rhythm to the year, and the good news is that many places with seasons don’t often see snow. If you’re just looking for a more temperate winter, it’s not hard to find. In fact, in some places the seasonal difference is negligible… maybe you wear a sweater or light jacket in the colder months of the year.

If you’re considering living in the heights, keep altitude limitations in mind—it’s not the best choice if you have a heart condition, for example.

Of course, this is again customizable. There’s a big difference between Medellín at 5,000 feet and Cuenca at 8,400. They both take some getting used to, but I’ve known many who can’t stomach Cuenca’s altitude—they wind up sick and miserable. The same people are OK after a couple days in Medellín.

Next think about the architecture and infrastructure that is typically found in a place with your chosen climate…

Do you see city streets with frozen puddles and icy lampposts? Quaint townhouses sunbathing along a small street on a spring-like day? Steep roofs few and far between as you gaze across a rocky, undulating landscape? Or is it simply sand and ocean as far as the eye can see?

This question backs you into considering the type of lifestyle you’re seeking big picture. Again, you could roughly divide your best retire-overseas options into types: city, small town, beach, and mountain. These are very general classifications, but breaking the world down this way can help you focus and progress your plan.

When you think about cities, consider the differences between modern and historical cities. Historical cities can have all the major amenities of a metropolis, but they were built hundreds of years ago. This means small cobblestone streets that don’t accommodate large cars (or maybe any cars at all).

Cobblestones are charming, but they aren’t easy on the legs and back—important to keep in mind if you like to walk. These cities are also less accessible for those with mobility limitations. You might not find ramps, for example, at the crosswalks or in stores… or anywhere.

When you think about beaches, consider the level of development you would be most comfortable with. Do you want to live in an established beach town where you might have to contend with tourists in season? At the other extreme, you could find an all-but-unknown beach where you’d have to install your own electricity and water source if you bought land to build a house.

When you think of mountains, remember, again, if altitude might be a health concern for you. Also consider if you’d be happy to be landlocked in a mountain retreat… or would you be happier with water nearby? Many popular mountain destinations feature nearby lakes… and some countries on our list of the best places to live or retire overseas even have mountain ranges near the coast.

One of the most important questions to ask yourself—no matter where in the world you’re thinking of retiring—is whether you’d prefer becoming part of a gated community or flying solo in a more local neighborhood. There’s no right answer, and each choice has its pros and cons.

Next consider your type of accommodation. Do you want to buy a place of your own? Build one? Do you dream of a house on land with room for gardens… or do you want a lock-it-and-leave-it condo so you’re free to travel when wanderlust calls?

How much room will you need? How much maintenance do you want to take on? If you’re not planning to live in the destination full time, will you have to invest in a caretaker while you’re away?

Answering these questions should help you draw yourself a pretty good picture of what you want your life overseas to look like.

Then you can shop that picture across the globe. Where could you find the lifestyle you’re imagining for yourself?

I pose these questions today not theoretically but with the hope that you’ll take the time to sit back in a comfortable chair and jot down your answers in each case.

That homework done, starting tomorrow and continuing through the rest of the week, our Live and Invest Overseas editors are going to do their best to help you connect your personal dots with the world map.

We’re going to take you on a tour of the world’s best places to think about living or retiring overseas right now.

This won’t be your average, run-of-the-mill tour. We’re not going to simply serve up different appealing destinations. We’re going to square them off against each other.

No place is perfect. Every destination has its pluses and its minuses and comparing them is the best way to find the place that’s best for you. 

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