Author and blogger Roosh V has published an e-book about looking for women in Colombia. He has spent more time there than I have, and has more and more varied experience; I can only comment on the portion I have experience with but all his advice seems very sound.
First, the part most guys are more likely to be interested in and actually do- short trips to Colombia to meet women you have already had contact with over the internet. Finding a woman who has a decent knowledge of English is unlikely, so to do this you will have to learn at least basic conversational Spanish. If you’re emailing you can get a lot of help with online translators and dictionaries but to actually go you’ll have to be able to talk about some basic things. There are a number of websites for this, www.latinamericancupid.com, www.colombiancupid.com, www.amigos.com, and www.amolatino.com among others. Women on these will all be very flaky but most men who go on these never go to Colombia or Latin America so you can’t blame them. Knowing some Spanish and having an actual date for going will help a lot.
The other option is marriage agencies, which charge more or less depending on what services you get. I have used them but I don’t know that they are necessarily worth the money or that much better than working on you own. They will provide translators who can help you through some initial conversations but of course at some point you’ll be on your own with the woman. They might do some basic screening but they can’t really protect you from scammers.
Many of these women are only looking for a free meal or a guy to send them some money. If you meet a woman, take her to a nice restaurant, and she says “Thanks, bye!” and jumps in a cab well at least you had a chance to practice Spanish with a pretty woman. I have had women come out and tell me they were looking for a visa. I have had women ask me, after meeting them and having a phone/email relationship they didn’t believe was going anywhere, ask me, “Can you at least help me get a visa?”, not understanding the only way you can do that is by being married or engaged.
The other common scam is just to ask you for money. If a woman you haven’t met asks you for money, obviously that’s a no go. Some guys obviously do it though, I suspect the aunt of one of my girlfriends sent her son to college and English school on such donations. More likely after you have met her she will ask you for large or small amounts- large if she is dumb, small if she is more sophisticated about it. She understands that $200 is not that much to you, and if she can come up with some sob story about some financial emergency or ongoing need you may give it to her. In a country where the minimum wage is $400 a month and most working people make that or little more, it’s a lot of money to her. If she can get a few guys to do it, she’s doing well.
If you are just going to meet women for the first time a hostel is probably fine to save money. Some are very noisy though so try to find out what kind of crowd they have. In Medellin the Black Sheep is very nice. Come with an unlocked GSM phone, per Roosh, and get a sim card, and you’re in business. (I bought a prepaid phone there but it is a real pain.) In Medellin you can get these from a kiosk on the ground floor of the Monterrey mall in the center, otherwise just ask around.
I have not been to Cali. I have been to Bogota twice for about five days each. Bogota is a stupendously ugly place. Huge, grim, appalling. Even most of the upper-class neighborhoods are pretty grim. The first thing I noticed was the lack of trees. Only a few of the upper-class neighborhoods (Alto Chapinero, Usaquen) have trees. It’s usually cloudy, usually chilly, and often raining, which considering it’s in the mountains at over 8000 feet is not surprising. The women have more Indian ancestry than in Medellin and are not quite as pretty on average. Nonetheless, because of its size it offers a lot more options than Medellin and I may go there again.
Medellin is a much more pleasant and pretty place. It does indeed have lots of pretty women. Many of these women are upper-class however and not going to be interested in a middle-aged gringo. Is Medellin overrun by foreigners? You hear that a lot, but while you will see a few close to the hostels, and in certain bars or maybe in Parque Lleras, otherwise they are rare. When you consider the small number of women who are serious prospects against the number of gringo suitors, it may be a little picked over. Again this argues in favor of Bogota.
The sexual marketplace is way different there. First the male/female ratio is quite skewed, and this is not just a pitch by the marriage agencies, I have observed it myself. A typical Colombian family seems to be four children, three girls and one boy. I have been at family gatherings where women significantly outnumbered the men in all age groups.
The pump-and-dump alpha male is not an exciting new addition to the culture there, he’s been a way of life for centuries, and plenty of women don’t care for him. Economic life there is a horrible grind- jobs are very hard to get, and if you can get a job it is probably low paid and you will be worked to death. Life for the upper class in Latin America is great- they have money, power and privilege above even what the rich have here. For anybody below that life is pretty difficult.
As a result a nice guy with a job is a pretty good deal to a lot of Colombian women. It’s a bit weird, going from a place where you are invisible to a place where you are treated well and valued. The downfalls are there but the upside is good. For a lot of guys this is the best option by a wide margin.