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TL;DR: Seoul, Korea. I loved living there.
I've not seen many cities on Earth. But, in making my choices, I'll share what Im considering.
Caveat: I've never been to any place on the African continent. This is an admitted blind spot. I've also been to only three European cities.
Not New York, Toronto, San Fransisco, Ottawa, Portland, Las Vegas, Washington D.C., Miami, Québec, Atlanta, or Halifax (sorry Nova Scotia, we love you!)
Not London (UK). Not Frankfurt. Not Sydney (Aus). Not Beijing. Not Kathmandu. Not KL, KK, Bangkok, or Singapore. Not Dubai. Not Colombo, Male, Kuwait, Doha, or Muscat (sorry Oman, we love you!)
No La Habana, ni Santiago de Chile, Cali, Arequipa, Cusco, y no á ciudad de Guatemala (disculpame mis hermanos de Guate!)
I think that the greatest cities on Earth have DEEP histories, offer diversity, and have been at the crossroads of the human condition.
Of the cities I've spent at least a week in (in no particular order):
La ciudad de México, México. (Pyramids, gardens, art, and food)
Istanbul, Türkiye (Hagia Sofia, Bosphorus, history)
Seoul, Korea (functionality, history, food, mountains, music)
Cartagena, Colombia (music, seaside, fortress, art)
Beirut, Lebanon [at least, when (2012) and how (with well-connected locals) I was there. Certainly, it's faced repeated harms in the past 7 years.]
Berlin, Germany (architecture, functionality, history, walking tour, art, festivals)
Montréal, Québec (one Canadian city needed to be on)
Ones I've not been to, but might list if I had:
Tehran, Iran (history)
Barcelona, Spain (Al-Analous)
Mumbai, India
Hong Kong
Tokyo, Japan
Serious question, how do you afford that much travel, or am I just that poor?
The first bit, living in Seoul, was youth and low cost of living in Seoul. I had debt, but my Thailand, China, and Australia trips were done on the cheap.
The next bit, living in Kuwait, was making oil money, zeroing out my debts, and having no mortgage and no kids. It was pretty sweet. But, still, I lived in the desert.
The next bit, living in Guate, was still no mortgage and no debt. My eldest was around for my last two years there. But, again, low cost of living and flying was a boon.
Since returning to Canada, I have only been to cities to which I can drive. I still pretty new to having a mortgage.
That said, I'm not planning any trips until sometime after 2037. If, yknow, there's still a world then.
Not sure how you can say all that, exclude London and then put Montreal on there… place is less then 400 years old!
Montreal was a late addition.
It's not that old, I'd agree. But, of Canadian cities that I could see as among the greatest in the world, it's Canada's nearest option.
Québec is older, over 400 years. But, Montreal is more of a world city.
Calgary is solid too, other than the fact that it's in Alberta.
Vancouver is beautiful but in my experience it generally smells like garbage.
Good buddy of mine spent 5 years in Calgary and has only good things to saw. The Tarsands really pushed things in that province out of joint.
I'd like to spend some time in Van. I was in Victoria for a few days and Nanaimo for a few more. But Van and Tofino were bridges too far on that trip.
Portland was the West Coast city that was outstanding to me. Victoria was cute. Seattle was excessive.
I like Seoul, but I liked Tokyo just a bit more. I recommend it if you get a chance. But like any city that big, your mileage may vary based on what you actually do and see.
I didn't live in Tokyo, but I did live near it for a little while. It was beautiful, but I'm a bit glad I wasn't in the city all the time. Just too much going on for my tempo.
Tokyo isn't a city though. It's a prefecture. Yokohama is technically the largest city in Japan.
Thank you for the in-depth answer.
I’d love to go back to Cartagena. I proposed to my wife there and we had an absolutely amazing trip
That was one of my see-before-i-die trips I made as a teenager. Based, entirely, on a profile in Nat Geo. Australia was another.
Iceland, Norwegian fjords, New Zealand mountains, and Haida Gwaii are nearest the top of my list for physical spaces. Rapa Nui would be a neat experience, but not wholly necessary. Hokkaido in Northern Japan would be a cultural experience I'd chase.
And, I'd really like to go on the ground from Djibouti to Cape Town on a circuitous voyage through as many places and nations as I can manage. Then, a flight to Libreville, Gabon and travel on the ground toward Ghana.