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North America is the world's third largest continent. Although most people think of North America as a region that only consists of the United States, Canada and Mexico; North America is actually made up of twenty three different countries, including Greenland, the Caribbean and all seven Central American countries.
Unless you have years to travel (we are jealous) it is probably better to break up travel to North America into several separate trips. A trip to the United States alone could take you a few months to see the main travel destinations. So, start with the country that interests you the most. While you are in that country, work through your new found friends and family and ask them advice on where to go for your next North American adventure. You can then use this system to travel around North America as you work your way around the North American continent.