THIS IS A WORK IN PROGRESS. I lived in Cali when I was a little girl, but since I left so young, there is much I don't know. Every time I visit, I am met with insanely weird laws and idiosyncrasies that just baffle me. These are some of the ones that drive me nuts, just be aware of them for that time you do decide to visit.
Things You NEED to Know About Cali, Colombia
Dry Laws are on when there is an important Fútbol match: On 11/27 America was going to play Quindío at Estadio Olímpico Pascual Guerrero. I don't care about sports, I can't even name a player on any Colombian team. I had no idea that the teams were playing, but as soon as I walked out the door to head out to lunch I started noticing the red shirts. Grabbed a seat at a restaurant and ordered a beer. I was promptly told that because there was a match, there would be no alcohol served from 4am on Sunday until Monday at 6am. I asked if this was just in the area, but no...this is throughout the entire city. There's no beer, no wine, no alcohol at all on either on or off-premise establishments. Supermarkets have police officers at the door to make sure that no alcohol is sold. If you get caught (as a Colombian citizen) the fine is 2 monthly salaries - ouch!
Wine is Controlled by the City: Much like the PLCB in Pennsylvania and the CALJ in Canada, Cali's government gets to choose what wines can be sold in the city. This means that if your wine is not approved by the government, no liquor store or restaurant can sell your wine. This also means that the wine selection throughout Cali sucks ass. Seriously. The beer selection, is decent with a good amount of German & Belgium choices, so I guess there is that. Restaurant culture also stinks, but it is getting better slowly (these were what I thought of as the best restaurants in Cali).
Taxis charge extra on weekends, evenings, and holidays: I don't like taxis in Cali. They are old, smelly, bouncy, and the drivers always try to cheat you by either not putting on the meter or going a longer way than needed (suckers - I may sound like a Gringa, but I lived here and know the city...and I have no qualms cursing you out if needed). On top of this, there's an unwritten rule that on weekdays after 7pm, weekends, and holidays there is an extra charge of $2000 COP ($0.63 USD). Just stick with Uber, they're clean, safe and cheaper.
To Grab an Uber at the Airport, go to the 2nd Floor: Yup. The first floor is for taxis only, so when you arrive, go upstairs to the second floor to door 1. Your carriage will await you there. Also, if you are grabbing an Uber in the city, try to do so away from the Taxi Cue. Lastly, someone from your group should sit in the front seat. This way the police won't bother your uber driver.
No Des Papaya: Papayas are gorgeous, especially in Colombia; but this phrase means that you should not tempt thieves or it will be your fault you get robbed. While I feel this way of thinking needs to change, it is great advice. This means you should not pop our your brand new iPhone or wear an obviously expensive purse when you go shopping. It's a bit annoying, I exercise caution everywhere, but in Cali this is something you need to follow strictly. The city is not anywhere near as safe as Medellin (no issues with popping out my iPhone in places like Poblado or Provenza) or like Cartagena where I felt safe everywhere (even when I visited Bazurto Market). So until the situation changes, make sure to leave your papaya at home.
Winter means rain, lots of it: Winter in Colombia means rain, lots of it. Cali is considered a Tropical Savannah, this means it has very clearly delineated dry and wet seasons, this is usually between March & May and October & December. The rain usually happens in the afternoon and at night. The rain is super powerful, so unless you want to get soaked, you should stay indoors while it passes.
Guachiman: If you see an older man with a machete walking around the block, don't be concerned. He's there to take care of you. He is the Guachiman (watchman in Colombian Spanish). He is paid by the block or neighborhood to keep an eye on things and look for unsavory characters. If you are lost or need directions, he is your friend. Tip him $1000 COP for his assistance and he will be your friend for life.
Watch Out For 2 Men on Bikes: It is illegal in Cali, Colombia for two men to ride on a motorcycle together. This is because back in the day, this type of activity meant either thieves or killers, so if two men are caught on a motorcycle by the police, they will be stopped, ticketed, and if they are caught with contraband, they will be put to jail.
Pico y Placa: In Cali, private car owners can only drive their cars on designated days according to their license plates. This is apparently according to the number your plate ends on. Won't really affect you as a traveler, but interesting to know. I think it has something to do with pollution and overcowding.
All Purchases Require ID: This still freaks me out. Every time you buy something with a credit card, you will have to show some form of ID to the person at the register. If you are Colombian, they will ask for your Cedula, the equivalent of your Social Security card. If you are a foreigner, a passport or driver's license will do. This is actually something country-wide, so don't be surprised if this happens.