First, congrats on the coming wedding and all the best! I've been to Jamaica twice, both times for friend's weddings. Resort life is certainly different than non-resort life, but if you're with a good guide, I never felt uncomfortable off the resort. I love seeing the actual lifestyles when I go do these places. The resort itself will try to sell you on a number of excursions, which are often overpriced, but fun. The resort can likely tell you reliable companies that will cart you around with your own agenda. One day a group of us just hired a van to take us around to various portions of the island, which was my favorite day there. Beyond that, the resorts normally tell you tipping is included, but you'll still be tipping most likely. It's good to make friends with the bartenders fast if you're a drinker. Tip your maids though, they get paid dirt relative to any of the other resort workers. When you get off the plane, everyone will aggressively want to take your bag for you, to get a tip. It's pretty hectic when you first go through it. The shuttle you take from the airport will stop at a friend/family owned bar/restaurant in the countryside, so you can get a beer and go to the bathroom, and they can pull you aside one by one and offer to help you "party". When you get to the resort, many people will tell you to come talk to them if you want to "party". If you are traveling outside the resort, you will often see children run out and look for handouts, they'll chase you down the road. You would be cautioned to not do this. However, if you want, there are ways to help out. We didn't do this when we went to Jamaica, but we did when we went to the Dominican Republic, we took school materials to give to some local kids, and I would suppose it's much the same in Jamaica on these issues. We asked our guide for a good place to do this, and he let us know when the best time/location. He did tell us later that in the future, shoes are a real commodity in the villages, and if we wanted to do something like that in the future, shoes would be the way to go, even just old shoes you were going to throw away. There is plenty of good food and drink to be had for the week. Get a Cuban if you like cigars, but the "good deals" are because they're bad fakes. Scuba diving and snorkeling can be a ton of fun in the right areas. Dunns River Falls is the "big" thing to do, and it's an okay time. We did it as part of a whole excursion. It's a great time, have a blast!