Because I usually travel solo, I would have to say that Montego Bay in Jamaica was the scariest, even thoug I booked a ship excursion. The island itself (what I saw of it ) was beautiful, but the vendors really scared the daylights out of me!
As part of our tour, we stopped at a straw market. I managed to get cornered in a small shop (more like a tight little hut) by 4 women, each trying to dell me their items. one actually was attempting to braid my hair despite my protests. Once I got out, I ran back to the van and sat there until everyone else was ready to leave. several other women said the same thing happened to them, even when they were in pairs.
It left such an ugly feeling that I will NEVER go back to jamaica.....and if it is a stop on a cruise I want to go on, I will stay on the ship and enjoy the pool.