I had friends who at the end of their stay there were stopped and robbed by the police on their way back to the airport.
Most Americans aren't aware of the fact that on these largely poverty-stricken Caribbean islands our customary rules of behavior and social niceties are not ordinarily on display; one must be ready for a much more rough and tumble experience than usual. I would be as likely chance trying to acquire a coin here as to walk around with a fat neon wallet sticking out of my back pocket.
They were in a rental car. Previously, they had rather adventurously, and to my way of thinking somewhat unadvisedly, driven all over the island without experiencing any problems and/or trouble, but at the end their luck simply, and just perhaps inevitably, ran out. It had suddenly become a matter of "all your money or jail". And when you're victimized by the police, what other authority can you possibly turn to? You keep your mouth shut, your head down, and get on the flight home...and consider yourself lucky at that.
This is how life works; one person has this kind of experience, another sees and remembers something entirely different. After my own multiple visits to both Jamaica and St. Lucia I took away the opposite impression; that the Jamaicans were barely tolerable while the St. Lucians were just fine. Go figure.
Having worked in the Retail and now wholesale side of the food business for over 50 years, one learns quickly about dealing with the public. I have been and still visit cities and areas of such here in the states that concern me more than those in other countries. Let's face it crime can happen just as fast in high dollar neighborhood as a ghetto. Having worked in a retail store that who knows what walks through the front door,one always needs to be aware of their surroundings. If you are the type of person who believes that you're in a safe place or location you need a wake up call. No nothing that puts you in harm's way ,just to be realistic to what may be around you. The time I have spent in retail stores has always taught me to have eyes in the back of my head. Most of all it's common sense.... I still do store visits in retail food stores from high rent areas to ghetto areas. Being street smart is not a college course.... nothing I ever learned in college could of made me street savy. One must always practice to expect the unexpected. You can't go through life in fear,but you can be aware your surroundings. One other note I did spend a good many years at the block.... as a meat cutter....
I have been to many, many seaports around the world. If you are going ashore in a place like Jamaica, hire yourself a good short pilot. That is a local who can serve as an all purpose bodyguard and guide. In Peru and Chile many of them were deaf and dumb, which cut out the language barrier. If you are looking for coins, get him to take you to antique shops, junk shops, pawn shops, etc. a bit off the beaten path, and ask about coins. Many of those type shops will have a cigar box with odds and ends which can often be bought quite cheaply. I got several coins from the 1700s that way. I bet there could be some old pirate type coins found there in the Caribbean, A? Beware of fakes goes without saying. Don't flash a roll, be ready to haggle, maybe take a friend along, and make sure your shore pilot is not going to roll you.
My friend, you are both very brave and dare I say have also been very lucky. My sole experience with just such a local guide for hire happened back in the summer of 1966 in the old city of Granada, the former capital of what had once been Moorish Spain. This particularly underhanded but eminently smooth-talking gent gradually ended up leading us on what slowly but surely became clear was in reality an almost interminably long wild goose chase from the beginning, and once we had finally caught onto his exceedingly tedious and increasingly annoying little scheme his originally promising employment with us was summarily terminated (though not with extreme prejudice, mind you). The problem with trying to cover all the angles from the get-go is that if indeed you can't trust the very person you have hired to guide and guard you, then the enterprise in its entirety, and usually sooner rather than later, begins to fall apart at its "touristic" seams.
On a side story, we decided to go down to Tijuana a few years ago. My wife wanted to find a particular piece of burnished pottery and I wanted to buy an old silver one peso. Unfortunately, it took till the end of the day and then I found three shops that had coins (overpriced) but I bought one anyway in the "Kentucky Gift Shop". On the way to get a taxi, one of the street vendors was selling sets of devalued coins glued on cardboard, so I had to buy one...fun!
Many years ago my then teenage son and I were strolling past some open air stores in Playa del Carmen (just south of Cancun) when the shopkeeper of a little bric-a-brac haven leaned out and hailed us with a hearty "Welcome, K-mart shoppers!" How could we NOT accept that invitation!
Yeah the last thing I want is to hire a person I don't know to show me around a city,country ,or where ever I don't know. That just sounds like poppycock! Like everything else in life you research and read.... Then you decide who ,what and where you're going to venture.... I've always been my own scout.....at 63 just about 64 ....I must of been doing something right! Having traveled through out Mexico,Central and South America, every land fall in the Caribbean but 1. Major cities in this country ....in sections most wouldn't go... Never even considered a body guard tour guide ..... no need just know what you're getting into before you leave the front porch.
My wife and I stayed at a resort in Negril about 10 years ago. We had a fantastic time. They treated us like royalty! Went into Negril one day shipping. Other than cigars and t-shirts we didnt see much to buy. The open markets were fun to see. The people were great. Very friendly and we had no probelms at all. I think you'll have a great time.