I've travelled all over the world and lived in LA for 22 years. Dubai is the least walkable city I've ever seen by a wide margin. It would hold that title even if the weather did not already make it feel like hell on earth.
The weather makes it impossible to have the city walkable and enjoyable. If you want to see another city less walkable than Dubai, it is Qatar. There isn't even public transportation there (though a metro line is in the works).
I was stuck there for a few days for a job and wanted to do literally anything other than sitting in the hotel. There was literally nothing within a 30 minute walk (in brutal heat) so a taxi was required, but I didn't have any local currency, so I asked the hotel concierge where the closest ATM is. I then had to walk 30 minutes, just to find a broken ATM inside of a little structure with a broken A/C. At that point, I realized if I walked another 30 minutes, I would be at the mall. 2 of the 3 ATMs at the mall didn't work. After 20 minutes of realizing the mall was full of Gucci and other designer shops which I had no interest in, I took a taxi 15 minutes to the next nearest mall. Again, nothing but designer shops. Taking another taxi to visit yet another (unfinished) mall, which was worse than the last two, not to mention only 1/3rd of the shops were even open, but according to multiple people and the taxi driver, it was the "hot spot to go". The taxi driver refused to park inside because the line of cars was hundreds long and would have taken ~30 minutes. I ended up walking 15 minutes from the highway to the mall.
Vegas? Most of it is sprawl and the Strip (where few people live) is enormous hotels that are actually pretty spread out.
I agree the Montreal core is fairly walkable. Cold is generally easier to deal with than heat. There's also a large connected Underground that people use when the weather is bad.
Vegas has wide pedestrian boulevards, escalators for elevated pedestrian crossings, throughways inside casinos, and even a pair of monorails. The Strip is mostly linear and there aren't long stretches with nothing there - food, lodging, entertainment, and (of course) gambling are never more than a few dozen feet away at any point.
But I have to say, Rochester, MN - the Mayo Clinic - has to be one of the more extraordinarily walkable places I've ever been: the whole city is not only interconnected underground between apartments, parking structures, and offices but there are plentiful underground facilities as well. It amazed me to have streets so empty when I first showed up: I had no idea where everyone was! The answer is: why on earth would you go outside? :)
But it's pretty much just tourist stuff: casinos, a mixture of crappy and mostly high-end restaurants, souvenir shops, bars. I'm not sure I can think of having seen a grocery store outside of rundown convenience stores. And the transit is fragmented because most of it only runs between hotels with the same owner.
So the Strip is walkable but mostly in the same sense that a big shopping mall with tower or two of apartments is walkable.
Toronto also has extensive interconnected underground walking space. Even though the weather isn't terrible it is often bad enough that you don't want to walk outside. You can still go many places downtown on foot without being exposed to the element. Walkable doesn't necessarily require good weather year-round although that makes it easier and certainly more pleasant.
To be fair, for Rochester that's an exceedingly small city core zone of a few square blocks that is interconnected like that. You're driving from where you live to that zone for 99% of the people working there.
The rest of the city is basically giant soulless suburb. I've had friends who have lived there for close to a decade now.
Though interconnection isn't common there are a number of older small cities in the Northeast with walkable, revitalized downtowns. I worked in downtown Nashua NH for a number of years and there were plenty of little restaurants, places you could run various errands, and so forth.
But the nice area was really only a handful of blocks in each direction. And beyond that you are in mostly rundown post-industrial mill town and beyond that it is very spread out.
The monorail(s) might be more useful if they were accessibly priced and not so far from the strip. At least walking through the casinos is a fairly interesting and air-conditioned experience.
Maybe it's the weather conditions what produces a city like that. I live in a city that reaches 110F every summer, and
walking is something I avoid as much as I can with that heat. (And I love walking)
Dubai is a horrible place to be a pedestrian, at least the areas I briefly visited. Everything is at a huge scale so the distances are extreme, and obviously the climate doesn't help at all.
I wonder if anyone has ever built a city, or significant part of a city, with either a purely subterranean transport layer, or all pedestrian layers a storey above? (Obviously I'm talking beyond a subway system.)
In Montreal, we have the largest underground complex called "The Underground City". It's a series of tunnels of a total of 32 km that allow going almost everywhere downtown (add to that the subway and soon the electric train, we could say almost everywhere in the city) without going outside.
Canadian cities (sans Vancouver) seem to have a lot of pedestrian tunnels (often doubling as downtown malls). In HK you can get pretty far underground as a pedestrian in some parts (you can basically walk between subway stations in an underground labyrinth to avoid rain).
Also, Minneapolis has a nice skyway network. Then there is La Defense in Paris where the pedistrian level is above street level.
Yeah Toronto has the PATH system and you can get around much of the downtown core that way (though I prefer not to...). Toronto itself is really quite walkable for hours in most directions if you live downtown. However to get to anything in further reaches of the city—Scarborough, Etobicoke, or Vaughn—it's far better to have a car. Living downtown and visiting the zoo on transit is a long stretch ;)
Calgary also has a skyway network (called the Plus-15 http://plus15.com/). Living there one winter was odd to me after Toronto—you'd never see anybody on the streets. And downtown Calgary is reasonably quiet on a normal, nice day. That said that town is also quite walkable—though it's best parts are relegated to certain parts of the city that are separated by less interesting areas.
Victoria, BC is one of my favourite walkable places so far. I also really enjoyed my time in Montreal, but I'm a little conditioned to the cold.
It has become a lot more pedestrian friendly compared to 15 years ago my first visit and 1 year ago my last visit. But the problem of afternoon heat cant be solved.
It takes time to build up a high density culture. Thicker skin, a bit more aloofness, etc.. many run counter to what is considered "good" in sparser area.
In my experience in London, the people living in the centre are not aloof, but it's the commuters who switch off their brains on the train or in the car and forget to switch it back on when they're in town. But that's an extremely broad brush, so don't take the categorization to heart.
I found this wasn't universal. Grew up in relatively unfriendly (especially for a Canadian city) Toronto and then moved to Chicago, found people were much more outgoing and friendly in the midwest, even in the city. In the bay area now and it seems like spending too much time driving with other angry drivers (from themselves spending too much time driving) makes everyone irritable.
Just have been to HK at Admiralty/Center. And the stairs up and down to get anywhere over the streets is super annoying. Especially at night. But surprisingly not much traffic, and lots of buses and trams. But maybe that was due to new year.
That's because you have been conditioned to look for the streets. The midlevel is amazing and protect you from the heat/rain plus makes your walk less of a pain (no need to cross roads).
One of the things I miss most about HK, having grown up there, is just how far you can get in a (roughly) straight line without touching the ground. There were parts where you could go for 10-15 minutes at a stretch, and that was ~25 years ago. I can only imagine that's grown since.
I also got the impression that Dubai wasn’t very walkable, but I’ve never been there.