I’d go with a city that has relatively little international tourism, and few multinational corporations with operations in the area. My nominees would be second-tier cities in South America (Cordoba, Valparaiso, Manaus, Cucuta and the like), regional centers in Russia (Novosibirsk, Yekaterinburg, Samara, Omsk and so on) and the surrounding Stans, and Pyongyang beyond the confines of an organized tour.
Even in a city with a lot of international business, you’re going to have trouble if there isn’t also a lot of tourism. When I was in Osaka (a lot of stuff there, but not as much a tourist destination as Tokyo or Kyoto) I could find English-speaking staff at the hotel, but not so much at even the larger department stores and non-business restaurants. OTOH, there were many businesses that seemed to cater to Koreans, as Osaka is apparently a gateway to S. Korea.
There is, however, no shortage of giggling schoolgirls who will cheerfully say “Hello” when you pass them on the street. Unfortunately for me, that seemed to be where everyone’s proficiency in English ends.
It could be worse, though. My parents went to Hungary while it was still Communist. Not only was there virtually no one who spoke English outside of Budapest, but when my father tried to converse in Hungarian (fluent, but rusty and heavily accented) he said people actually seemed afraid to talk to him. He ended up getting most of his directions from the local rendőrség
(police) – who all seemed most interested in talking to him.
Probably the small, out of the way cities in any country will be the most difficult for tourists to communicate with the locals.
I hope your friend used this as a learning experience and will not go to another country and expect them to speak English (except places like England and others where English is their official language) in the future. My fiance is going to learn this lesson the hard way as well unfortunately. We are going to Finland in November (not even Helsinki or anything but up into the center part of the country) and I’ve been studying the language but he just keeps saying that people there will speak a lot of English so he isn’t worried. I think he is going to be very hungry and lost all the time if I’m not around to help him out but we shall see who is right.
For Japan it is important to note written English is taught in all schools. They are not all taught to speak English. When interacting with the younger Japanese it is convenient to have a notepad handy. What your saying may make no sense to them but if you write it down for them they understand it completely.
To me Japan is the most English friendly countries to visit(other then those that are English speaking of course)
European countries are in general easy to communicate in. Most people I deal with even if they don’t speak English speak 2 or 3 languages with Latin bases. There is a lot of common ground to work with, a few key words can convey most messages.
My world travels have yet to take me anywhere I consider English unfriendly. People commonly complain about France but that’s not my experience and I feel those people complaining have more basic issues.
In France it isn’t hard to find English speakers. If you come off as a jerk though few of those people will admit they speak English so not to have to deal with you.
A simple thing you can do in a foreign country to not offend people is be able to ask if they speak English in their language. If you ask in English even if they do speak English you are conveying the message “I’ve come to your country and can’t even be bothered to attempt your language”
OK? 
I’m simply saying that you often hear people trot out that joke when they want to show how stupid Americans are, that they don’t even know a second language, when in reality most Americans don’t have the *need *to speak a second language. The United States is larger than all of Western Europe.
I’m curious to know if English-speaking Australians commonly know more than one language, or if that joke would apply to them just as easily.
Montreal
From some quickie research, Australians are just as monolingual as Americans.
“In Australia only 12% of Year 12 students study a foreign language.”
http://blogs.crikey.com.au/fullysic/2010/05/28/the-broken-record-australians-are-too-monolingual/
http://www.languageonthemove.com/blog/2010/02/03/monolingual-mindset-in-the-lucky-country/
http://www.griffith.edu.au/australian-strategy-asian-language-proficiency/report/skills-shortfall
Still, despite all the similarities in culture and lifestyles, Australians, along with Canadians, New Zealanders and Anglo South Africans, usually get a pass from the accusations of negative cultural traits Americans are so often burdened with. When was the last time you saw a thread where people pile on loud Australians, fat Afrikaaners, or bland Canadian cuisine?
One of Montreal’s main universities, right in the heart of downtown, teaches only in English. There are many, many restaurants and, especially, pubs that are predominantly English. I lived in Montreal, and my French never got much better than it was when I arrived, because I didn’t have to use it very much. Montreal is way down on the list of major international cities that are difficult for English-speakers.
?? Have you BEEN to Montreal? Everyone speaks English. Well, maybe not everyone, but you can’t swing a dead cat without hitting an English speaker.
Was this Delta/Northwest from New York to Moscow direct for $496 last summer/autumn? You should have gone! Hardly anyone spoke English, but who cares? The only difficult time I had was when the train lady was asking me what I wanted for dinner. I had no idea what she was asking, and no one in my berth spoke English, so it was awkward for a few minutes. But eventually someone recalled the word “fish”, and that was that.
The Moscow Metro was incredibly easy to navigate. Cyrillic words aren’t difficult to recognize and remember, even if you have no idea what they mean or how to pronounce them. It was no more difficult than taking the subway in New York or DC.
Seconding Japan. Although I know it asks for cities, from what I’ve seen and heard from others, it’s pretty tough to find people who can speak English at a conversational level with the exception of those majoring in it, business people, or airline stewardesses. Their educational system does a poor job with teaching it. Most people know a few English words that are peppered in magazines, but that’s about it. I’ve even heard English words used in a way that wouldn’t seem right to a native speaker (such as “handy” literally meaning an object that is small enough to be held in your hand, as opposed to the meaning convenient or useful. That was a tough one explaining to my students.) I will give them credit that they know that their English is bad and are extremely polite and try their best to help you out anyway.
Next time, go for it! You’d be surprised how well you can get around on sign language, smiles, and a couple words. Seriously, I know people who live in freaking China for years without learning a word of the language. People spend months backpacking around Southeast Asia without knowing Lao and Vietnamese. Trust me, you’ll get the swing of things just fine.
Moscow is easy. Learning to read the characters comes to you really quickly. Once you get outside the city it gets harder.
Japan was far more difficult where I couldn’t read many of the signs. At least the subway had Latin characters, but I was lost otherwise.
I’m not an expert on Finland or anything, but in my experience most Scandinavians speak English. Sometimes they speak English so beautifully that it’s actually embarrassing in a way, listening to someone be more eloquent than you in your own language.
Like I say, I don’t know central Finland, so I could well be wrong, but there is a fair chance he will be vindicated.
I agree with Kyla that Eastern Europe can be tricky when you speak only English. There might be a couple of main streets filled with tourist shops/attractions and staffed with English speakers, but in many cities as soon as you leave that area there can be a real dearth of English. Travelling around there also made me realize that even though I don’t actually speak French or Italian or Spanish, I can often at least partially interpret signs and whatnot just from the few words we have been exposed to (being Canadian I have a large food item vocabulary in French, because all food is labelled in French and English), and by guessing at words that are similar in English. Once I hit Eastern Europe though, all bets were off. The language is so different that there is no way to puzzle out meaning.
I wouldn’t really call them English unfriendly though, and I agree with kenner116* that not knowing the language shouldn’t turn you off going somewhere. I’ve gotten by in several foreign cities with only a couple of words (I usually try to learn ‘hello’ and ‘thank you’ - they might think I’m an idiot, but at least I’m a polite idiot), and a combination of miming and guessing. It got ridiculous in some cases, and I ended up doing ‘Marcel Marceau orders a sandwich’, but it all worked out.
*ETA: and even sven, who snuck in while I was posting!
I know people who live in Montreal who don’t speak a word of French.
I know it feels lame to walk around with your guidebook in hand, but it really does make things easier, because then you can point to the address of your destination to passersby. The last time I was in a country where I REALLY could not communicate with anyone was when I was in Albania in 2008. (I’d been to some other countries where I seriously don’t speak the language, like Turkey, but I’d stayed on the tourist trail, which made things relatively easy. Albania doesn’t have a tourist trail.) Most of my Eastern European traveling had been in places in the Balkans where they speak South Slavic languages, and I do fine with that, but I felt incredibly out of my element in Albania, where they also don’t have very many street signs, so even knowing the address isn’t all that helpful.
Basically, I walked around with my Lonely Planet Western Balkans in hand and showed the address of the places I was going to people. I had strangers walk blocks out of their way to lead me to restaurants. I’ve found that most people enjoy helping tourists out. (To be fair, Albanians also LOVE Americans, which probably didn’t hurt.)
Sana’a, Yemen is fairly Arabic-only, though you do get a few Ethiopians who can get by in Italian.
I actually bought into that way back in my youth. As an undergrad at my university, it was “common knowledge” that all Europeans were multilingual. Then I spent some time in Europe and was amazed at how many spoke only their native tongue.
Istanbul. You could find an English-speaker in a pinch, but many, many Turks know no English or have only the basics. This was good for developing my Turkish skills, as I HAD to learn it to survive, and even today I know the Turkish words for most basic stuff around me, how to ask where something is, how to order food, introduce myself, etc.
really? I met a BUNCH of Turks that spoke English in Istanbul. Some of them worked in the tourist industry (I was a tourist), but some of them were just random people. One was this guy I met…I don’t even remember where, but he was just a student, and he introduced me to several of his friends. They all spoke passable English.
I guess that wasn’t representative of the population at large?