Jimmy’s favorite cities

As I hypothesized in a previous blog post, where we choose to call home is an important decision that affects long-term happiness. That said, I’ve lived for at least two months each in eight separate cities across three continents, and visited perhaps a few dozen more. And from what I’ve seen, there’s no perfect city that I would never want to leave.

There are, however, some cities I’ve enjoyed living in, and many more that I enjoyed visiting for a short period. I've found that good way to differentiate between cities I enjoyed spending time in is to categorize them into three buckets:

1. Cities I would be happy to settle down and raise a family in (a home base).
2. Cities where I would want to repeatedly spend summer/winter vacations in (a vacation base).
3. Cities that I think everyone should visit once because it’s fun or interesting, but I wouldn’t particularly want to visit again (a tourist destination).

In this post, I’ll share my personal choices for the best in each bucket, as well some additional thoughts on each selection.

Favorite home base: Vancouver

This is not a biased answer as far as I can tell. (I say this because I’ve lived in Shanghai for the past seven years, but it probably doesn’t crack my top 3. I prefer London, which is my honorable mention for this category, and possibly Singapore as well.)

That said, there are huge quality of life differences between neighborhoods in Vancouver. In my opinion, the best neighborhood (which luckily isn’t nearly the most expensive or even the most popular), and the one where I would almost certainly settle in if my family and I were to move back to Vancouver, is Kitsilano.

In Vancouver, the best season by far is summer. Vancouver is a city for spending time outdoors, and summers here are never-ending days of sunshine and 25-degree temperatures where the sun doesn’t set until 10pm.

The biggest disadvantage of Vancouver is the average wage level. People take a substantial pay cut to live here. For example, software engineers in Vancouver make 30-50% less than their counterparts in Seattle and San Francisco.

Vancouver is a fantastic place to retire to. Just don’t move here expecting to further a lucrative career.

Favorite vacation base: London

In an ideal life, I’d probably want to spend 1-2 months of each year in Europe, and ~80% of that time would be in London.

It’s difficult to get tired of London. It’s the most cosmopolitan city in the world and the most important cultural center, with five airports that (used to?) offer flights to almost anywhere. It’s at once the mother of all tourist destinations and the gateway to a limitless number of tourist destinations in the British Isles and continental Europe.

The main disadvantage is the food. The UK has some of the highest quality whole foods I’ve seen anywhere, but the taste of the local cuisine is just uninspired. (A notable exception is the full English breakfast, which I miss dearly.) Additionally, food from other cuisines is readily available - but usually at exorbitant prices. I was made painfully aware of this when trying to find good dim sum places in the city.

Honorable mention for this category is Tokyo, which is the opposite of London in many ways. Every couple of years, I’d have a strong urge to visit and lose myself in the streets of central Tokyo, in hopes of stumbling upon a tiny restaurant serving exquisite food that I will likely never encounter again. Visiting Tokyo is always fun, but I always want to leave when I inevitably begin to feel that I’m just a “gaijin” (外人) among the local Japanese.

Favorite tourist destination: Barcelona

A poet once declared that Barcelona’s La Rambla was “the only street in the world which I wish would never end.” Having walked its length myself, I can understand the sentiment. There’s also the Atlantic sunrise on the beach, the breathtaking uniqueness of standing in the nave of the Sagrada Familia, and the strikingly strange Park Güell. There were many moments from my visit that felt “touristy” but were just too memorable to ignore.

The language barrier makes another visit less attractive, since it would prevent me from understanding the city locals on a deeper level. If I spoke Spanish, I’d probably want to go back once every few years. Regardless, I still have a pact with my wife to revisit Barcelona when construction of the Sagrada Familia is finally complete.

Honorable mention for this category is Las Vegas. A place with countless casino resorts that serve free alcohol is just never going to be boring. I suspect many people regret going to Vegas, but definitely not because it wasn’t fun.

Unexplored destinations

I still have a lot of traveling to look forward to (when this global pandemic finally concludes). Below are the locations that I most look forward to visiting for the first time. I expect that this list may contain some eventual replacements for the selections I've made above.

• The Mediterranean aside from the Côte d'Azur (particularly Venice and most of Greece and Croatia)
• Orlando (purely due to Walt Disney World)
• The Maldives
• Fiji
• Berlin
• Sydney and Melbourne