We LOVE Montego Bay and Jamaica. As others have said, the trick is to get outside of the dock area, which can be a very depressing. On our last trip, we hired a taxi driver for the day (negotiate the rate BEFORE you start out). We went rafting on the Martha Brae River (a GREAT excursion-I highly recommend it!) and Barry, our taxi driver, was waiting when we were finished. He then proceeded to take us on a tour all over the island, telling us stories that the average tourist would never hear. He is a native of the island and very proud of it and has fantastic stories to tell about the history and such. He took us to pick up his daughter at school then took us to the home he was building for a bite to eat and to meet the rest of his family. They were so gracious and happy to have us visit them and the views of the port area from his homesite on a hillside were spectacular. We have always found the majority of people in Jamaica to be very kind and very anxious to leave you with a good impression of their homeland, as they count on tourists for their livelihood.
Whatever you do, be sure to get out and see the island and don't just stay in the port area. Jamaica is a beautiful place and what you see when you get off the ship is not a fair representation of what it has to offer.
Kathy