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Been a while since I did one of these, and the addition of Canada is intriguing.
1. New York: Does almost everything better than almost everyone else.
2. DC: I love the grandeur, the density, the public spaces, the feeling of importance.
3. Montreal: I've felt a little disappointed every time I've gone to Canada. Except when I went to Montreal.
4. Chicago: It's been two years since I've been there. That's too long.
5. Los Angeles: Like 20 great small cities in one.
6. Boston: The harbor, the history, the youth, the vibrancy.
7. New Orleans: It's going to be really hard for anyone to knock it out of No. 1 on my list of most fun cities in America.
8. Charleston: Gorgeous. Severely underrated food scene. Everything to like about the South.
9. Savannah: Like Charleston. Somewhat prettier but less of a city feel, therefore a notch lower.
10. Seattle: There's something I really love about the Pacific Northwest.
Could have been on this list but there were only 10 spots: Providence, Burlington, Portland (Maine), Austin, Miami, Philly
Want to include it because I love it there but I don't think it's big enough to qualify, even though it was on someone else's list: Newport
Didn't really like them when I visited but it's been a long time and I want to give them another chance: Toronto, Vancouver, Denver, San Diego
Forever excluded from these lists because I haven't been there since 1989 even though I want to put it there: San Francisco
01. Toronto - It's the most balanced and well-versed city in North America and it isn't even close. Don't even bother trying to argue this fact. It's not too much of anything, but it has something for everyone. It's not East Coast, it's not Mid-West, it's not stereotypical Canadian. It's undefined. It's big, clean, safe, and exciting. It's politically important. It's financially and economical important. It's culturally important.
You can choose the dense urbanity of Toronto city proper, or one of the safe and wealthy sprawled out suburbs like Mississauga, Oakville, or Markham. It's why I choose to live here and no where else these days. It's why it's one of the fastest growing metros among OECD nations.
02. New York - Probably the most important city in the world with London and Tokyo trailing just behind. It's massive and the beacon for finance and culture.
You feel like a somebody just by living there. That's a unique trait. Everyone should live here at least once, even if it's just for a few months.
03. Boston - I've always had this fascination with Boston. I love the dichotomy between the blue-collar history, and the super white-collar present and future. Many of the world's best universities are in and around Boston -- extremely educated and interesting populous. Loads of character as well. Probably the most historically important city in North America.
04. San Francisco/Bay Area - Basically the Boston of the West Coast. Whenever you have an extremely educated and wealthy population, good things naturally follow. Again, loads of unique character in this city.
05. Chicago - I visit Chicago maybe once every two years or so. It's kind of like Toronto but with more balls (and I mean that in both and bad ways). The architecture is just one of a kind. Just so many beautiful buildings from the 1900-1950s that still stand today. It's a fun and lively city with a great professional sports tradition. The Mid-West charm is real.
It's probably the only city on this list that I couldn't live long term, though. It's just too dangerous these days, and while it's a very big metro, as a white male, much of this city is off-limits to me after dark. This kind of makes Chicago feel smaller to me than it really is. Some areas are simply "no go areas" for someone like me.
The other 5 cities are just the typical cities that I've stayed in a few days and enjoyed i.e., Montreal, LA, Vancouver, Miami, and Seattle.
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