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City Guesseris often substantially easier thanGeoGuessr. Sometimes you start a video and, immediately, there’s a license plate with “California” written across the top, or a sign that says “Tottenham Court Road Station”. GeoGuessr would often drop you on a country road with nothing but trees and weather to steer you, but City Guesser’s urban environments and moving videos give you so much more information to work with.
That’s not to say there’s no challenge at all. You can choose whether you want to tour cities only within a specific country or continent, but select “worldwide” or a region with languages other than your own, and suddenly all those shop signs are a lot less useful.
Walking in Tokyo Shibuya on a sunny day - 4KWatch on YouTube
Walking in Tokyo Shibuya on a sunny day - 4K

That said, it’s not the challenge that keeps me playing. City Guesser is part ofVirtualVacation.us, a website that lets you browse videos taken while walking, driving, or flying above locations all over the world. I already watch a lot of videos like that on YouTube channels such asNippon Wandering,TokyoStreetViewandSeoul Walker. You can find videos like these for every major city, and I imagine VirtualVacation.us is just acting as a wrapper for browsing them.
(The answer was Auckland, New Zealand and I was correct within a mile.)