There isn't any direct land route from São Paulo to Colombia. Right now the easiest way to go from São Paulo to Colombia is leaving São Paulo, travel to Peru, ride trough Ecuador until you reach Colombia.
There's 2 main ways to make this route, crossing Bolivia (about 4500 kms from São Paulo to Lima) or going trough the Interoceanic Highway (about 5700 kms from São Paulo to Lima).
Is possible to arrive in Colombia trough Venezuela (you can leave São Paulo, ride all way up to Manaus and then enter Venezuela by the BR-174 and then cross to Colombia - about 7400 kms until you reach Bogota) but Venezuela right now is in the verge of a Civil War and the border between Venezuela and Colombia was closed not long ago and there's the risk to you when arrive in Venezuela be surprised with a new closing of the border between the 2 countries.
If I had to choose a route to arrive in Colombia right now I would choose the Interoceanic Highway route in a heartbeat.
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