We planned our route around many factors, and are still constantly tweaking it for the best possible experience. We're striving to create a route that prioritizes safety, sightseeing opportunities, points of interest, best practices, and staying with those who have opened their home to us. All distance calculations are underestimates (because they're based on drawing straight lines along the route), but should give a good idea as to the length of the trip. Check out the country links for route details about each country. In general we're sticking to the Pan-American Highway where possible, using the details on Wikipedia (PAH Overview, PAH in North America, and PAH in South America. Please feel free to comment on the route, suggest changes, point out places of interest on and off the route, and help us make the most of the trip! Thanks!
We're still working out the details on the route, and will continue to make minor modifications up to our departure date and along the way, but here's a preliminary outline that will give you an idea of where we're headed. Click on the map for a closer look.

Most of the maps were taken as a screen shot from RunThere.com, an exercise route calculator most likely not meant for this purpose. :) For the few countries Google Maps does not yet show highways for, maps from Mapquest are displayed.
Click on the map for a closer look.
Distance: 1,549+ miles Planned Stops: Palm Springs, California Beaches, Redwood Forest Why this route?
The coastal route will be a nice alternative to the I-5 straight shot, and we get to see the Redwood Forest.
Going through Tuscon will allow us to drop into Mexico at the least dangerous main entry.
The next stop on our route is Mexico.

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Distance: 2,109+ miles Planned Stops: Puerto Vallarta, Mazatlan Why this route?
Coming in through Tuscon (border-town is Nogales) is currently the safest main entry to Mexico because of the drug activity in Juarez/El Paso and Tiajuana. We'll get a full tank of gas just before leaving the States, and shred south to get out of the border area as quick as possible. The Pacific Route is supposed to be quite a beautiful drive, and I'm really looking forward to it!
The next stop on our route is Guatemala.
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Distance: 239+ Miles Planned Stops: Why this route?
Following the Pan-American Highway (PAH)
The next stop on our route is El Salvador.
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Distance: 171+ Miles Planned Stops: Why this route?
Following the Pan-American Highway (PAH)
The next stop on our route is Honduras.
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Distance: 83+ Miles Planned Stops: Why this route?
Just following the PAH, unfortunately the route through Honduras is brief.
The next stop on our route is Nicaragua.
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Distance: 226+ Miles Planned Stops: Why this route?
Following the Pan-American Highway (PAH).
The next stop on our route is Costa Rica.
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Distance: 343+ Miles Planned Stops: Why this route?
Following the Pan-American Highway (PAH)
The next stop on our route is Panama.
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Distance: 350+ Miles on land, another 350+ on a boat (5-day trip) Planned Stops: Colon or Portobelo
Why this route?
For social, political, and practicality reasons, there is no road between Panama and Colombia. The 'Darien Gap,' as it's called, stretches for about 60 miles between Central and South America and is inhabited by natives, guerillas, and dangerous terrain and circumstances. The best way to get between these two countries is by plane or by boat. Boating is much more of an experience, as we will get to tour the San Blas Islands - basically a paradise inhabited by natives. It usually takes about 5 days to make the trip from Colon or Portobelo, Panama to Cartagena, Colombia, plus any time we spend waiting for a boat to take us (some travelers have reported waiting weeks).
We're also considering taking a plane from Panama City to Quito, Ecuador, if the political situation in Columbia turns unfavorable. We'll make that decision closer to our departure time.
The next stop on our route is Colombia.
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Distance: 954+ Miles Planned Stops: Why this route?
Coming into port at the popular tourist city of Cartegena, we'll make our way south, through Medellin, over to Bogota, then south to Ecuador. According to the US Department of State travel advisory, the coastal town 35 miles west of Cali is still considered violent, so, unless conditions improve, we plan to avoid Cali by going straight from Bogota through Neiva to Popayan, rejoining the PAH there.
As with most countries, but especially in Colombia, we will be traveling by daylight only and will avoid rural areas as much as possible.
The next stop on our route is Ecuador.
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Distance: 515+ Miles Planned Stops: Why this route?
Following the Pan-American Highway.
The next stop on our route is Peru.
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Distance: 2000+ Miles Planned Stops: Machu Picchu (Incan Ruins north of Cuzco) Why this route?
Following the Pan-American Highway, except for a detour to see Machu Picchu.
The next stop on our route is Chile.
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Distance: 2097+ Miles Planned Stops: Santiago Why this route?
Following the Pan-American Highway, except for a short detour to visit Santiago. Then we'll cut across the Andes into Argentina before we get too far south.
The next stop on our route is Argentina.
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Distance: 2020+ Miles to Tierra del Fuego, plus 2492+ Miles back up to Buenos Aires
Planned Stops: Ushuaia (the southern-most city in South America), Possibly Iguazu Falls (Corner of Argentina, Paraguay, and Brasil)
Why this route?
The PAH stops in Buenos Aires before it follows Argentina NR-3 down to Ushuaia, but we'll take a shortcut south, since we're coming back up to Buenos Aires to fly home.