Japan
How many people speak English: 10%
What it's like as an English speaker: The Japanese learn to read English in school but their conversational skills often lack. When in doubt, write it out. All you need to get around is to show people your destination in Romanized writing or in kanji. Most taxis have GPS and if you give them the address or show them the Japanese address on your phone, they'll get you there. Most places these days have English menus on hand, with pictures galore. At every turn, you'll find Japanese people who feel apologetic for not being able to speak better English, and who go the extra kilometric mile to help you out.
English signage now abounds on the streets of Tokyo, Osaka, Kyoto, and in train stations everywhere. If you need help, ask the station master or policemen stationed at huts in front of every station and they'll happily guide you, sometimes even accompany you. I recently had an Osaka train station employee walk me from the station exit to the gym I was looking for after he decided my Kanto Japanese was the equivalent of not really understanding Japanese. (Osaka and Tokyo have different dialects.) Tokyo also rocks a government-made app, "Tokyo Handy Guide," that offers maps and sightseeing functions.
What Japan has to offer: Visiting Japan is like stepping into a neatly made time machine. You can jump to the future in the robot restaurant, or explore the past in the beautiful temples of Kyoto or the Art Deco mansions of the imperial family at Tokyo's Teien Art Museum. Gaze upon Tokyo's landscape of neon from 52 floors up in the observatory of the Mori Art Museum or lose yourself in the mystical inner gardens of Meiji Jingu shrine. Now that the absurd dancing-after-midnight ban is over, you can enjoy the club scene until 4am, or if you luck out, head to a fancy "love hotel" and experience the wonders of body sonic and in-room vending machines that will melt your mind. The really classy ones have rental costumes -- from both the ancient past and the future.
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