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After a few times of trying this out, you can now see some of the places I have been. Considering that all of these places are within the M25 (the motorway which surrounds London) and taken at specific times, it is not unconceivable that I have not in fact been to all of these places. You could easily state that you are say, on the corner of East 14th and 3rd in New York and twenty minutes later be by the Flat Iron Building at 5th on Broadway. Because these are timed carefully, it makes it even more plausible that I am in fact at these places, when I am not.
Please read the disclaimer! You can find this and more, including the explanation - as well as the pro's and con's of using spoofed geolocation on the ZDNet iGeneration blog.