Latin America In Two Months. Sky high Andean cities, Caribbean beaches, rainforest villages, and more hours traveling by bus than I care to count. We’ve been ticking off the days for months now, and it’s finally almost here. On April 29th we will start our two month adventure through Latin America. To be fair, we are really only visiting six countries in Latin America, which is still probably a lot for two months, but we’re going for it. Starting as far south as Santiago, Chile (where we are currently living) and heading north until we reach Havana, Cuba. We’ll be sharing updates and pictures along the way here, so be sure to check back to see what we’re up to. But before it all starts, here is our (very) rough itinerary, plans, and expectations for the next two months.