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How cold do Boston and Denver get in the winter? A lot of snow?
Philadelphia is a very walkable city, has good public transit and a fair amount of bike lanes. You're not going to escape the cold in Philly but it's not bad, in comparison to northern minnesota philadelphia is practically tropic. Last year we got hit hard by snow, but that's pretty rare. This year we haven't really had any real snow storms and the weather has been pretty decent. it's cold, but cold here is like low 40s during the day and there are days when it's considerably higher.
New Orleans is a good choice for warm and very walkable.
Curveball choices are Honolulu since it's so isolated and Los Angeles. Los Angeles is a funny choice, because the majority of it isn't walkable and has poor mass transit, but because it's such a big city, the part of Los Angeles that is walkable is probably as big or bigger than many other cities.
How could you talk about walkable cities and not mention New York? Four seasons and certainly not the brutal cold and winters you find in northern Minnesota. And as too many people fail to notice, NYC isn't just uber-expensive Manhattan. There are vast areas of moderatley priced housing in Brooklyn, Queens, and the Bronx, where its perfectly easy and normal to live w/o a car, and many people do. (Staten Island is subway-challenged, so you do need wheels out there.) And don't get feraked out by the size of the place. Most people live in and identify with their neighborhoods more than with the city as a whole.
walkscore.com will provide you a detailed breakdown of walkable cities. In gist, SF, NYC, Boston, Philly, DC and Seattle are your top 6. However, most of the top 15 are very walkable if you stay within two miles of the core. I've lived in NYC, Chicago, Atlanta and now Denver. But traveled to all but one of the top 25 metros. Best bang for your buck with seasonal weather is going to be Philly. If you want the ultimate experience then it's SF or NYC. Arguably, Boston and DC will buffer between the ultimate choices.
I'm leaving Chicago off because of your disdain for brutal winters. I'm leaving Seattle off because of your disdain for extreme climates. Miami is a wildcard that can be argued. Denver is a sleeper.
I have a few of these cities in mind. I am also considering Minneapolis. I could handle the winter down there, as long as I am living in Minneapolis or St. Paul rather than the suburbs.
I think ST. Louis is a viable option, its pretty walkable and the transit ok plus the winters are way milder.
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