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If you're thinking of taking a trip in North America, I personally reccomend Toronto.

Although it's not nearly as large as some US cities (which can also be taken as a plus), it's the largest city in Canada and has a very wide range of appealing qualities.

What I personally love most is the multiculturalism of this city. Toronto has a very large immigrant population, from all corners of the world. This allows for a nice variety in terms of entertainment, food selection, and the types of people you can meet around town.
 

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"Hands of Stone"
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I have, and will again. We (my wife and I) spent a one-week vacation there and had the time of our lives; highlighted by a day trip to Niagara Falls and dinner atop the CN tower.
 
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