We found a huge difference in price between the excursions offered by the resort we stayed in, and the cars/vans/minibuses waiting on the road just outside the resort. Just asked the driver what we should see, also what we wanted to see, and for CAD$20. he spent 6 1/2 hours with us! I think there were 26 of us, maybe 28. Good day for him, good day for us.
We had thought to take him for lunch, but obviously he's got contacts on the island. He took us to a reasonably priced restaurant, lunch was less than $10/person, and because he brought us there, he got his lunch for free!

We stayed in a resort near Fallmouth, but I'm sure drivers with vehicles will be found just outside most, if not all, resort in Jamaica.

You've received some good input. Dunn's River Falls would be at the top of my list, BUT the water is chilly and the rocks are slippery. If you like history, Rose Hall Great House (reputedly haunted) is nice. Rafting on one of the rivers might be enjoyable, while a visit to a coffee plantation or Appleton's Rum to see the production process may interest.

We've been to Jamaica twice and are heading back in the near future. The people seem to be the happiest we have encountered on our travels, but the cautionary note about the crime potential should not be ignored. I ran into the same issue of wanting to be paid for taking a photo of an individual, but honestly I can't fault those folks since their standard of living is so much lower than ours.

Love Jamaica. Took several trips there. While staying in Montego Bay my wife and I hired a local guy to give us a look at what the tourist do not normally see. We had a rental car and this fellow took us to Dunn River Falls but then after that we ventured up into the hills and we saw the real beauty of the island. I took some photos of school children that probably have never seen white people. This photo has won me several awards.

Be careful with talking photos in the public market in Montego Bay. I was shooting a lady who was carrying a load of bananas on her head and she came over to me and demanded $$ as she told me I was going to make a lot of money with those photos. She obviously does not understand vacation photos vs commercial photos. But never the less just be careful.

A trip to Negril is almost mandatory, The sand there is almost like sugar. The people are friendly and the coast line is awesome. Rent a boat with a local and they will take you around to the caves the pirates use back in the day. Ricks Café is a local bar and grill that host the cliff divers and the best sunset on the island.

Take a lot of photos and share with us on the return...

Also ..... From Montego Bay you can go to Negril along the coast to see the light house. If you go to Dunns River Falls, you'll be in Ocho Rios. The drive on A3 towards Kingston thru' mid island is nice and there are many photo ops. You can also go along the eastern coast towards Port Antonio. Along the way you can get to the Blue Mountain area. We had to turn back on that road to the mountain due to a mud slide. Continuing on, you can get to the Blue Lagoon area for a neat raft trip down the river. Not a whole lot to see in Kingston, possibly Bob Marley Museum if you're interested and Port Royal.

If you happen to drive, be very very careful esp. around towns. In case of a fender bender you may want to be judicious about if and where to stop. Our rental car was rear ended by some kids in Ocho Rios (just some very minor stuff) and we got out to get the driver info etc. and drove to the police station to file a report and was informed by the police that stopping was ill advised due to the high crime esp. after dark. Fortunately our CC covered the damages.

Have fun, it's a beautiful island.