Haha in his or her face! Tell 'em!
Well like I said, I generally know where stuff is, but it’s more like I’m just walking there on auto pilot. And anyone who’s ever been to Pittsburgh knows it’s more of a city of neighborhoods – ask me how to get to the Point or the North Shore, I could do that. Ask me how to get to the zoo from downtown? You generally want to get a good map or GPS.
I’m not sure about the US, but in my experience Smartphones in Australia are so cheap (literally free on a phone contract; second hand ones readily available and even brand new “no-frills” models available for change out of $100) that quite literally everyone in major cities who wants one has one, and anyone who doesn’t have one doesn’t need one and/or has an enormous beard, a Penny Farthing, and owns a cereal cafe.
I have to say I agree with the OP - but I’m one of those lucky people who’s extremely good with orientation and navigation and finding my way around. The idea I could spend any useful length of time in a city (ie more than a couple of days) and not know where major landmarks and stuff were is, quite frankly baffling.
I used to live in an extremely touristy area, in a non-touristy role, and even though I’d never go to any of the attractions, I certainly knew how to give people directions to them (even if those directions were “Drive to the airport and then catch a plane to Sydney, because that’s where the Harbour Bridge you’re looking for is located”).
Interestingly, though, we used to have a flatmate who was like the sort of people the OP described. He’d lived in the city his entire life and had no idea where anything that wasn’t our flat, his work, his girlfriend’s place or his parent’s place was. He honestly had no idea - I mentioned going to a fairly substantial shopping centre which was about 30 minutes drive away to get something, and he had no idea where it was.
I think that the privilege **drunky ** was referring to was the time and means to play tourist in their own city. In a lot of urban areas in the US, the people who work in the tourist areas don’t live there, either because housing isn’t available or it is unaffordable.
Most everyone under the age of 80 has smart phones here too. 
No, I understand that, as it truly does make sense. But I’m absolutely positive that no matter how much you do something by rote while not really paying attention, you totally could’ve at least headed them in the right general area by saying either right or left. I just can’t comprehend that would be too much for anyone’s ability.
Well, I guess it depends on the regions, but this is generally why you want to have a map…
(I’m not kidding, this is what happens when people try to give directions in Pittsburgh. Usually, if it’s in walking distance, and you look trustworthy, they’ll show you where something is.) 
Maybe they really, truly didn’t know. Some people really, truly cannot tell you that the door of their workplace faces a certain direction relative to an invisible landmark eight blocks away.
And there are also people who just aren’t very curious, and refuse to learn to find their way. There are people who get hopelessly lost in airports even though there are detailed signs hanging within view of almost everywhere, telling you where to go. The idea that the location of gate B20 is discernible from a sign saying “Gates B 10-25 →” does not cross their minds.
This. I’ve spent plenty of hours walking around Boston, but from most locations, I wouldn’t be able to answer that question.
First, I have no freaking clue what you mean by “Boston harbor”, because that’s adjacent to most of the city. You could want to go almost anywhere.
Second, the streets are a maze of twisty little passageways, no two the same. It’s very hard to give directions in Boston to anything that isn’t very close by. And 8 blocks isn’t close enough to be easy, even if the waiter guessed that wherever you ended up was where you wanted to go.
Third, everyone takes the T. Locals rarely drive around, and most don’t walk far, either. So they have no particular reason to know local geography (which isn’t easy to map to a grid, like it is in many places)
If you’d asked for direction to the nearest T stop they could probably have answered that.
I have this problem. I know where the thing is. I could easily walk/drive there. But my direction giving skills are lacking. I know that it’s forward for a while then right for a while - but I also know that there are hills and that the city isn’t exactly a grid and there are streets that just end. I’m not really sure whether the thing is on 1st or 2nd or possibly even 3rd. I also really have no internal sense of distance - so, I know it’s close, but 5 blocks? 10 blocks? I really just know that I could walk right there.
Well, I thought I knew my way around Boston. I was just downtown today. There was an event for singles, an urban race/scavenger hunt. I was a little apprehensive, but nothing ventured, nothing gained. The ticket said to meet at Central Wharf at 1:00. I got a bit dressed up, left nice and early, and was there in front of the Aquarium by 12:45. No one showed up. I walked all the way out to the end of the wharf; plenty of people around, but no one organizing any sort of scavenger hunt. It turns out that I think they meant Central Wharf Co. (a restaurant) and not Central Wharf (a wharf).
On the other hand, I found the harbor. I felt like jumping in.
↑ ↑ ↑ This = Way cool tude…
The only other thing I will say about this, since much of the discussion (because part of the OP) centers on Boston–
I have known a lot of people from Boston in my life and a lot of people not-from-Boston as well, and while people not-from-Boston aren’t necessarily especially good at geography (knowing where things are in their own communities, the US, the world), people *from *Boston are disproportionately the pits where geographic knowledge and understanding is concerned. Sure, I’ve met a few geographically-savvy Bostonians, but the bulk of those I know have a *really *bad sense of geography. “What’s the capital of Europe” bad, “It takes what, a few hours to drive from Los Angeles to Miami?” bad. (Both of these are perfectly true.)
Maybe it’s the result of living in a place where the street layout doesn’t make a lot of sense, or maybe it’s this idea of the “Hub of the Universe” where nothing outside the city signifies, or maybe it’s something in the water, I don’t know, but when it comes to otherwise intelligent people who lack even basic geographical understanding, Boston seems to lead the league.
That does not sound like a great notion…
Damned Klingons!
Did you read the part where I posted that my wife has a Smart Phone and for whatever reason couldn’t get a signal? I posted it early on:
No, I can’t blame them one bit. That fucking Big Dig started a few years after I was born and ended what, just a few years ago? 2005? During that time everything kept changing in Boston. We went half a dozen times and every time it was damn difficult to navigate. And the city is confusing. NYC is built on a grid and is sort of planned. Boston? Not even remotely. It’s just a disorganized mess. And I love Boston, but damn, it’s confusing.
All this tells me though it the OP is one damn annoying tourist. You need to bring your own maps and know how to get there. Your lack of planning does not constitute an emergency on anyone’s part. I don’t own a smartphone, either, for the record, and neither does my husband. We opted for tablets, but you know, for years and years we did without, and had printed maps ready to go. Hell, for a while we used to keep a map of Boston in my car, we went so often.
And what’s all this about milennials? I’m 40 fucking years old. Gen X, and I hate you Baby Boomers and I hate you milennials too. Get off my lawn - both of you!
But you have a PokeStop with a lure going and tons of spawns! 
Do you mind telling the name of the restaurant so us locals can see how close you were?
So…You ask the hostess how far it is to Boston Harbor (the harbor or the hotel?), when she tells you she doesn’t know, you question her as to how long she’s lived there (I’m sure they were perfectly pleasant questions, and didn’t come across as condescending at all.) So she has lived there for 32 years (but how long has she worked at the restaurant?)
Then you jump over to the waiter, and grill him for how long he’s lived there, and then two others. I’m guessing you weren’t asking as politely as you thought you were.
As others have said, the harbor is huge, seeing as though you were there on Fourth of July, and the fireworks (which are nationally televised) are shot out over a part of the harbor, where the Charles empties into it, there are plenty of road closures which could complicate giving directions.
So which part were you trying to get to? The touristy portion near the aquarium (which is one direction), the touristy portion new the Federal Courthouse, Bank Boston Pavillion and Harpoon Brewery (different direction) or looking at it from the Northend?
So, what was the name of the restaurant, and which part of the harbor did you want to see (or end up at)
This. I once asked a co-worker if she lived east or west off the street - the street that ran due east/west - our place of business was. As in, is the sun in your face or at your back both ways? Even when phrased that way, she couldn’t tell me.
That’s very confusing wording. Phrased that way, I can’t tell what you’re asking either. (“west off the street”? “both ways” of what?)
If the street she lives on runs due east & west, doesn’t she live on either the north or south side of the street?