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20 days beginning in Nicaragua

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If I have 20 days and am going to be flying into Nicaragua with the hopes of traveling north (up to Guatemala) what is a reasonable estimate for where I should fly out of? Will I comfortably be able to be in Guatemala in 20 days (and not have missed TOO much) or should I fly out of a closer country?

I intend on meeting up with my friends in Nicaragua and assume they will have already spent a week in Nicaragua by the time I arrive and then moving up along with them.

Any tips/ideas/clarification would be wonderful!