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Starting the third 90 day period earlier than 6 months if I leave the country

10 years ago
I've been doing a lot of research on travelling for longer than 90 days. I understand that you can renew the visa after 90 days (and no sooner), and then after 6 months you have to leave the country and start the process over again.

If I were to leave the country after 5 months for a week or two, then return, does that mean I start a new 90 day period?

Also what do most people do about return flights in this situation? Will I have any problems flying into the country if my return flight is past the 90 days? I'm coming from Canada.

Thanks!

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