I reckon this board needs a bit more levity and positive discussion of far off lands, as opposed to the more heavy discussions of such.
I'm currently in Hong Kong and had dinner last night with my close friend from Singapore. He was meeting a former regular tennis partner of his. Ended up being a very successful finance guy who had the kind of heady global financial destination journey that feels like was so very common in the 80s/90s but has dissipated a lot with globalization. He's Turkish, so started in Istanbul out of university, moved to Amsterdam shortly thereafter where he met his now wife through mutual friends from back home. They moved to Chicago for a few years before he was poached and headed to NY for a decade, then London for a few years after a change before being moved to Singapore, and now HK where he's been split between HK and Singapore for the last 5 years.
Among other things, we had a great conversation about lived experiences in different places and commonalities. Funny enough, of all their global footprint, they actually said Chicago was their favorite city they'd ever lived, save the weather. If it had mild, more northern Mediterranean style weather, it would be their winner. Granted, they admitted partly it was that they were married there and had their honeymoon years there, but still they found it a very special sort of city.
Some of this has been covered in bits and pieces in the travel thread, but we have a diverse group of people with travel experience and opinions here, thought it could be fun. And FWIW, I'm thinking cities, not regions or beachy resort areas or ski destinations, stuff like that.
For me, Ive always split the discussion in my head to "favorite cities I'd happily live" and "favorite cities to visit/that I've visited". Some are an overlap of both.
For example, Chicago. My former home for 10+ years, I'd happily live there again, either city proper or near burbs, but will never do so short of a significant life event that draws me there as 35+ years of Upper Midwest winter was a enough for me.
Similarly, London. My first trip to London in my mid 20s was a wonder. An eye-opening experience. I had never "got" the draw. Always thought Anglophiles were a bit puzzling. But after I spent a week there I fully got it. My subsequent 10 or so trips over the next 15 years only further solidified it but also that I would love to and could happily live there, in any number of different neighborhoods spreading out from the center (not just the tourist who has a great time staying in Mayfair and walking around Hyde Park and Kensington and thinks that's London). Obviously a blindingly expensive city, especially rent and real estate, and not my favorite weather, but I'd choose it over Wisconsin/Illinois winter/spring any day.
To visit? Hong Kong is up there. I had prolonged considerations and discussions about moving here for work reasons a few years before COVID, and wasn't opposed to it, especially after spending some time with expat friends here. But a variety of reasons, not least of which is the continued shift from the uniqueness of HK to more like just another major Chinese city, that ship sailed. I still adore it, there is an energy and feeling here that is palpable and very special that I haven't found anywhere else. And while its very very dense and crowded and populated and competitive, it feels oddly more approachable and liveable than a place like NYC (something that actually came up in the conversation at dinner). More than anything, even though I could make HK work with a family, its too hard to be on the opposite side of the world.
Similarly Jakarta. Wrote a love letter to it in the travel thread. Amazing place Ive really enjoyed getting to know over the last few years. And the cost of living/affordability/friendly culture is appealing as an expat. But even more remote travel wise than HK and not developed enough for me beyond Jakarta proper.
My final 2, favorite places to visit but could never live. First, domestically, is New Orleans. Man I absolutely adore everything about that city from food to culture to history. But I could never dream of living there. And that's not even thinking about the pea soup thick summer humidity that makes Florida humidity feel like a nice spring day.
And foreign, in Asia, definitely Tokyo. Can't say enough awesome stuff about Tokyo, but its also so very overwhelming. Perfect place to have an incredible experience for 3-10 days and then look forward to another trip back down the line. In Europe, I absolutely have LOVED the 2 times Ive been to Salzburg, think its a truly underrated gem, but its just too small. I don't even think I could spend more than a few days there. And nearby, Munich. Another place that I have always been drawn to and fascinated by (and Ive never even done Oktoberfest). Have a great time there but am not devastated when its time to depart.
Honorable mentions to Barcelona, Nice/Marseille, Istanbul, and Singapore.
On the other hand, least favorite city is always and foreign, Brussels ;D
Love the topic Wags. We have some in common.
Dubai. Having lived there and grown to understand that it's actually very affordable and easy, it's become one of my favorite places to visit and I'd live there again in a heartbeat. People comment about how it's all "fake"...yeah, so have you been to central London lately? Manhattan? Plus it's so safe there, and the government services are pleasant and efficient.
Cape Town. I go there annually for a business conference and have been staying for a week before/after. This year we flew my team of 50 there for our annual meeting as well. Cheapest place with great food, great scenery, great wine, hiking, easy to get around, and something for everyone at every price point.
Melbourne. The city center is nice and the neighborhoods with the cultural/ethnic twists - German, Greek, Italian, etc. are fun to explore. Weather can be bad. Nice getaways down the Mornington peninsula or to the Yarra valley (wine!) as well.
Jakarta. repeat above. Would live there again.
Singapore. like Dubai, one of the last remaining places on the planet where crime is illegal. So much to do and explore for a small place. Awesome food. Would live there again as well!
Moscow. Controversial one I'm sure but other than the traffic it's safe, has lots to offer culturally, food, recreation. Not crazy expensive. Spent 10ish days/month there for 10 years of my life and found it very appealing.
Cities I despise: London (loved it 20 years ago), Beijing, LA, Johannesburg, Paris, Kuala Lumpur
Honorable Mention: Brisbane, Perth, Chicago.
I used to rate Hong Kong but it's just changed too much and lost its personality and some of its vibe.
I loved living in and going to school in Antwerp, would probably be willing to do that again.
Also really enjoyed Edinburgh, and would like to go back there on a more extended trip.
1 Chicago, NYC, London, Tokyo, Paris, Mexico City
All are megacities with enough neighborhoods that we could find our desired path, even as the city changes over the next decades of our life. Good friends live there so our social life doesn't start from scratch, and tremendous food cities.Arts up the wazoo. Good public transportation.
2 Osaka, SF, Copenhagen, Belfast, Toronto, Singapore, Bangkok
These places are missing something for us. Just not quite tier 1 "spend the rest of my life there, never moving." But I wouldn't hesitate to spend 5 years in these cities awesome food and people, but no close friends living there. Bangkok and Singapore are both troubled in their own ways. Belfast and Copenhagen and SF are too small. Toronto is just Chicago in Canada. Osaka is grand but it's not Tokyo.
Everything else isn't on the list, tbh. Our list may shift if we need to cut costs, but I don't think that's in the cards.
It will be unlikely that we ever sell the house in Chicago, but we may rent it out for a few years to go exploring?
Edit: This list is just places we've spent significant time. There's a wide world out there that I'm largely unaware of, I'm sure.
Love and would live in any day:
Large: London, Chicago, Montreal, Toronto, Ho Chi Minh, Barcelona
Medium: Edinburgh, Genoa, Montpellier, Rouen, Cork, Belfast, Milwaukee, Boston
Small: Galway, Westport
Liked but probably won't return: Singapore, San Fran, Nice
Like but would never live: Paris, Rome, Dublin, Kuala Lumpur, Tokyo, Twin Cities, DC, Florence, Denver
Too young/broke to have truly experienced: NYC, Seattle, Vancouver
Actively dislike: Phoenix, Houston, DFW, LA.
If I overlap this with my wife's list it's basically cork, Montreal, Genoa. She'd probably add Cape Town.
She hasn't been to Edinburgh Belfast London or Toronto though.