Where is the worst place you have ever gone on vacation?
For me it was Cancún. It was the "place to go" when I was a youngin, so I gave it a try. I ended up hating every day of being there. I am not much of a beach guy and prefer to wander versus being stuck at a resort for an entire week. Many of the "Americans" down there seemed to be first/second generation Eastern European types that were very rude to the hotel and restaurant staff. You could drink as much beer as you wanted for free, but to keep costs down, there were only like four brands of beer served. The only American one was Coors Light. The resort would not let you bring girls you met at the night clubs back to your room because of the all-inclusive thing. The Mexican police had a thing for arresting gringos late at night who appeared drunk, were caught urinating, or were drinking beer on the street, which is illegal there. I would buy a 40 ouncer of Sol at 7/11 each night and chug it as I walked to the night clubs with my head on a swivel looking for the policia to roll up on me. You also have taxis constantly rolling up on you and asking you if you want "company". They then take out a portfolio of pictures of naked women to show you, which are all local prostitutes. I assume they get a referral cut if they take you to one of the hooker's pads. The women in the Yucatan are more indigenous looking than northern Mexico. The only good-looking women were the güera types from Cuidad de Mexico and a small fraction of American women on vacation. On the beach, I constantly had to shoo away Mexicans trying to sell me everything from blankets, pinatas, and sombreros to cocaine, ecstasy, and marijuana. When you reject the drugs, they then think they can at least get you to buy some Cuban cigars. Also, the weather was miserably hot and humid. I would never go back.
I have asked this question to several people at work, and they all said the same place: Jamaica. One was robbed in Jamaica. Others complained how Jamaica is so ghetto and everyone wants to sell you marijuana. Another person told me how a woman at her hotel got raped by a Jamaican guy who climbed over the fence into their resort. Ya Mon!
Bonus question: Have you ever gone on vacation somewhere that you thought would suck, but ended up having a great time?
I didn't particularly care for Cancun either. However, I went to Puerto Rico for a week several years ago and found the people to be warm and caring. When I was walking around the marketplace in Cancun, a shop vendor wanted to discuss politics and Donald Trump with me. No way I was going to engage in that discussion, but in Puerto Rico, everyone strongly identified themselves with the USA. Try San Juan, I bet you will like it.