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Month Stay In Oaxaca, Mexico

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Me and my boyfriend (both 21 yrs old) are planing a months vacation to Mexico. We plan to drive from Tucson, Arizona. We have plans to rent an Airbnd in Oaxaca for about a month and travel to Mexico city either on our way down or on our way back. We want to get the most out of it and are determined to hit all the best surrounding cities. So far we have heard everything from complete praises to absolute horror stories. I speak pretty ok spanish. So I am here to ask, how dangerous will it be? Is driving crazy? Do I need special insurance? normally when we travel to places in Mexico closer to the boarder we do just fine. How much money will we need for the month we are planning to stay? (keep in mind we are both very low maintenance, don't mind making do and truly want to enjoy the authentic experience rather than the luxury tourist version) Will a month be too long? What are the must sees?

Would really appreciate the help

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