Which City You'd Want To Retire In?

Retire In New York

In the past few years, I’ve traveled quite a bit, fall in and out of love of different cities. During that time I also asked a lot of people the question above and been getting varied answers. One funny thing happened: none of them mentioned New York.

It is probably the most coveted city in the world. We see it far too many times in movies. We dream about it as we sing along “Concrete jungle where dreams are made of, there’s nothing you can do…” We just can’t wait to post our Top Of The Rock selfie as it is a two level bump in swagger point. However, like a magnet, it attracts many but equally unappealing to many as well. I’m on the latter side. It’s interesting to see how bipolar New York is. With that in mind, what is it really that makes a city so lovable that you’d want to spend the remaining years of your life in?

I enjoy digging in to the answers, as it sometimes peels off a multitude of different layers that I otherwise could not see from my conversation counterpart.

Retire In San Francisco

Someone who choose San Francisco would most probably enjoy chilly weather, laid back, and like to be at the center of where tech & innovation are.

Someone who choose London definitely realize the danger of making friends with umbrellas, being cloudy most of the time with little chance of ever escaping drizzle. At the same time, they most probably enjoy the melting pot of people, culture, and food. Do you know that Chicken Tikka Masala is British inspired Indian dish? That should speak loud in itself about the city.

Someone who choose to retire in Bali are likely to do so to find balance between his mind and heart. His left brain and right brain. And would like to affordably do so.

Retire In Slovenia

Someone who choose Chiangmai or Ho Chi Minh probably has seen too many episodes of Bourdain and dream of the exotic slow life while having access to awesome street food 24/7 and 365 days a year.

Someone who choose Tokyo most likely are fascinated to be part of the rich culture and to live in certain values — excellence, servanthood, honesty among many –. Find comfort in a sense of order on top of enjoying the never ending supply of good food. (Insert # of ramen shop in Tokyo & Michelin-starred restaurant)

Someone who choose Jakarta probably doesn’t have much options but to cheer himself up every day that despite of the deadly traffic, well he got his family, friends, and what he needs just 10-30 minutes around his housing complex. And there’s always Gojek for the rescue anyway in times of need, from food to massage.

At the end of the day, I have a feel that the city you choose to retire represent the kind of life you wish you are living now shall money is no issue. It reveals a bit of your aspirations, preferences, values, what’s important to you, who you are under the skin and who you’d want to be. And for that my friends, is how I get to know you better. If by any chance I ask you that, it means I’d like to give you a shot to be in my circle.

Welcome. We might end up in the same city. I could use a friend to cross my few final bucket list 😉

So, which city you’d want to retire in?

Written By

Fellexandro Ruby

Food photographer, and story teller sharing his passion in food, travel, culinary hits and highlights. Always on the mission to make you drool. Founder of Wanderbites.com


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    • I can imagine Taipei. Nice people. Nicer than HK probably? City is much less packed. Much less expensive overall (housing & food). And I do speak Taiwanese Hokkien. Haha.

    • From what I heard from friends that been both in HK and Taiwan, they all said Taiwanese is nicer. And with the Hokkien you can go travel to more places than the normal mandarin speaker, Capt.

  • Tokyo is most tempting to me. At least for now, since i haven’t explore other parts of Japan. The city is charming in its own way. Modern yet still very traditional in many ways. Everyone has good manners & respectful towards each other + low crime rate + useful (yet unimaginable) innovations + uber kawaii stuff + squeaky clean (even the streets glow!)

    Only problem is, it is a freaking expensive city :'(

    • It is actually not that expensive if you know your way around it. I’ve lived there for an accumulated of 60+ days. I’ve found ways to save by (1) buy groceries and cook my own (2) there’s always 380 Yen rice bowl for the rescue (3) property is actually much cheaper than singapore, you can find a studio of 27-30 sqm at USD 90-110K which is almost impossible to get in Singapore

      I would go to Tokyo too. My biggest barrier is actually language & finding work that relates to my field.

  • I wouldn’t choose a city at all, especially if I’m at retirement age. I would choose a small island (something like the Gilis) to get away from the hustle and bustle of cities. I’m in my mid-twenties and already considering living on an island

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