The best reason to retire overseas is to improve and change your lifestyle.
Instead of the question, “What are the best reasons to retire overseas?”, the question should be, “What is the best reason to stay where you are, and retire where you’ve worked all your life?” Did you choose that location because you wanted to spend your entire life there? Now that you’re retired, you have freedom. When you have freedom, you should exercise it, and that should take you to new places, new people, new experiences and a new life, but you can always return to your old life.
For me, the question is not why you should retire overseas, it’s why you shouldn’t retire overseas. I have had a foot in two countries (the US and Costa Rica) for many years, and it’s the best of all possible lifestyles because when you get tired of the weather in one place or if you want a change of scenery, you can go somewhere else. When you have two homes, you can go from one to the other.
One of the most successful retirees I know is my friend Gunther who comes to Costa Rica from Spain every spring. He’s originally from Switzerland and also has a home in Santa Fe, but he lives in Spain because he’s been married to a Spaniard. Gunther just makes a big circle from Switzerland to Spain to Costa Rica to Santa Fe and back. I can’t think of a better way to live. It’s just a question of your tolerance for airplanes as to whether you choose two or three places to live.