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Excursion through Mexico and Central America. Where to end?

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Next winter in the month of January i am studying abroad for a short term program that ends around January 21-25th. I want to be on my way towards Argentina where i need to be March 1, 2010.
I want to travel overland hopefully wih a friend but possibly by myselft through Central and southern mexico, Guatemala, El Salvador, Honduras, Nicaragua and Costa Rica.

I hopefully am going on a separate trip to panama this summer so i want to fly out of San jose, costa rica into quito, ecuador. I would like to go to Colombia but i have somewhat conflicting reports about being able to fly into Colombia without a plane ticket out becuase of strict restritctions. Also i am somewhat concerned about safety in Colombia although i understand it has improved. I will then travel through south America to Argentina.

Anyway does anyone have advice is on about a 10-15day trek overland from Mexico City to San Jose, Costa Rica? Is this even possible? where should I stop? Are buses the way to go? How do i maximize my time?

Thanks!

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