I made that trip by bus. Crossed at Ipiales. The bus ride is VERY long. Try to get a nicer bus.
We got held up when we close to the border on the Ecuador side. We stopped and waited and waited. People got of the bus and were walking around and smoking on the highway. I thought perhaps there was a wreck or the ubiquitous rockslide. So after a long while, I asked, "Does anyone know whats going on?
The old lady sitting next to me says very loudly, "It's the BLACKS! They're blocking the bridge! They're no good!" So I'm in back, and a nicely dressed black guy that strikes me as being a gringo turns round and looks at me. And I just shrugged like, "This ain't my fault!"
So after three hours of sitting, the chief of police finally convinces the protesters to go home. And we made it to the border. I stayed in a hotel in the little town on the Ecuador side before crossing. Don't remember the name, but the people were really nice and I may have stayed another night if my 90 day tourist stamp wasn't expiring.
I get a taxi to the Colombian border the next morning. The aduanas stamped me in with no trouble. I said I wanted 90 days in Colombia, and the officer just said, Welcome to my country, sir.
I got my bag and crossed into Colombia, and my first experience was to get a taxi shakedown. The guy told me it was $5 to get from the border to the bus station. I get in and we get to the station which wasn't very far. You can walk it. Then he tells me it's $15. So I say, "Bullf+cking sh1t, cabron! You're getting 5 dollars like you said!"
He insists that it's $15 and I end up giving him $15. I hadn't spent enough time in Colombia to know how things work, and that's what they take advantage of. Ipiales is a little town and I figure the chief of police surely knows this cabbie. And whose fault will it be if he says I ripped him off? So I figure I don't want to be in trouble in Colombia my first 15 minutes over 10 bucks. If I had it to do over, I would have chucked 5 dollars into the front seat and said, "F+ck you very much, marica. Call the damn policia, ladron!" And then I'd have got out. But I didn't know the dealio at the time.
Then I get into a little camioneta, and this driver is OUT OF HIS MIND! We're passing other cars around blind corners through the mountains the entire way. So take some vodka for that ride. I was wishing I'd had a drink.
I stayed one night in Popayan. The people were nice to me, but I wasn't impressed enough to stay. I saw a guy pooping on the sidewalk. It's very industrial and as a whitey Gringo, I felt like people were constantly watching me. Perhaps they just didn't see many gringos and found me interesting, but I didn't feel comfortable. So I left the next morning.
I had to change buses in Cali to get to Medellin. I walked outside, felt the blast of heat in my face and was like, "Nope, no Cali for me." And then I went to get on my bus. I couldn't find my bus, so this 20 year oldish kid helped me and carried my bag to the bus. I was worried that he was going to take my stuff or something, but he was fine. I tipped him a couple of dollars which he needed for his ticket to go where he wanted to go.
But that trip up from the border would have been stellar if not for the crazy ass driver in that little van. Holy cow. An then there were soldiers on the roofs of the little towns we passed through. And it's a lot of desert in Southern Colombia. Very hot bus ride. The bus will stop and soldiers will get on and stand in front of the bus, and the bus will let them off at their trucks.
So, it's a very exciting journey! Get ready!