Here’s a little gem from the web that tests your ability to locate yourself within the world - the GeoGuessr Challenge!
This game drops you onto a random point on the earth - a city, a beach, a road in the middle of nowhere - using Google StreetView and makes you guess where are in the world. You have 5 rounds and get points the closer you are to the true location.
As a simple tip, try looking for elements unique to a certain place: the terrain, writings on signs or roads, car models, or even the people. You can usually walk or pan around by clicking and dragging, and zoom in and out using the mousewheel.
Play the game here: http://geoguessr.com/