Hello All! Very interesting thread here. I have only been to Cozumel, Jamaica, Grand Cayman and St Maarten/Martin. Jamaica is the only stop that involved anything less than complete comfort from a safety point of view, however nothing serious. It is indeed one of the prettiest islands geographically, and one of the most mature politcally speaking. In Ocho Rios we took a river tubing expedition (off of the Carnival Triumph) and it was great fun. We drove up into the coastal mountains on a disintegrating road, and the scenery was spectacular. The White River was beautiful, and is part of their drinking water system, which meant it was very clean. The staff at the tubing establishment were very friendly, their only exaggeration being how "dangerous" the river was--it was pretty tame! The terminus of the raft ride was a little clearing with a "jerk shack--free samples", and we got a free beer or soda. We contracted with the tour drivers to take us to Dunn's River falls and pick us up at a later time--they were quite amenable and prompt.
Dunn's River Falls is pretty, but a lot of tourist-y activity goes on. You are best not to follow the signs that point to the exit, but go out the way you come in. The exit is blocked by about 500 vendors, who all want a piece of you. We had got sucked into buying "custom carved" fertility statues for $30.00 US. Albeit it from a friendly, charming fellow, but he had our names carved into them before we knew what was happening.. We were not interested in anything else other than a pound of Blue Mountain coffee, and several of the vendors pulled the "you disrespect me, mon" when we said no to buying. With 900,000 inhabitants, and probably 800,000 affected directly by the tourist industry, it certainly limits their options and you may understand why the "hard sell" is so important to them.
No problems in Cozumel or Grand Cayman, GC is more British than Britain.
St Maarten/Martin is my favourite island so far. No hassles, great shopping, friendly, well-educated people and beautiful scenery and beaches. You get offered pot, but a simple "no" will dissuade them from bothering you. We rented a van for three days and drove around the island several times. A little exciting, but worth the money. It seems everyone on the Dutch side speaks English, a little less so on the French side. We had a super time there during the week we spent in January.
An observation: As a Canadian, I have found that frequently the treatment I receive becomes more positive when I reveal I am Canadian and not American. I am not tarring everyone with the same brush, as I believe that the bulk of Americans are great people. However, I have encountered the stereotypical American on vacation who looks down on anyone who isn't from the US of A, finding them a little substandard. It is easy to see why someone from a country like Jamaica would be resentful (and perhaps rude) to someone who obviously looks down on them. How would you like to owe your livelihood to someone who looks down their nose at you?
As many of the respondees here have stated, there are plenty of parts of town in major US (or yes, even Canadian) cities that you would feel just as uncomfortable in at night than somewhere in the Caribbean!
Thanks for all the introspection and sharing, Tim T