I enjoyed every minute of Jamaica.
Upon arrival in a somewhat hot unconditioned airport, it already set the mood for my trip. Within five minutes of picking up baggage and finding our hotel shuttle bus (although we had more than enough offers for a taxi), we found someone (actually we had been approached by two people already) whom offered to sell us some grass.
Who could pass? Happens that person was our shuttle driver. Hilariously with a shuttle full of people, he pulls over for a minute, does a pickup, and hands it over (quietly of course).
It felt very free, although of course illegal. Theres a sense of chill in Jamaica.
I wouldn't advise for it or against it. The last thing you want is trouble, however, if it feels right...
We also traveled to Dunn's River Fall in Ochos Rios on a given day, unfortunately, I was terribly hung over at 9 in the morning, and puked on the bus the way there. Partly due to the fact that the driving was ridiculously scary—high speeds, rocky roads. I felt like I was on a roller coaster. The driver was kind enough to have me sit up front with him to avoid motion sickness. So, yes, watch for crazy driving, also Dunn's River was pretty ridiculous, and a waste of a day. It was like a shallow waterfall, and lots of markets selling the same things. It wasn't anything special however maybe a family would enjoy it.
So, in short a lot of drinking and grass goes a long way. Jamaica is a must-go, I fell in love the moment I stepped on the island. The people are very relaxed, chill, it makes you take a step back and relax.
Couple of tips:
Always bargain well for a price and don't let the pressure to buy something come into play. A simple "no" is all that's needed.
Otherwise relax, no worries, mon.