Luggage and bags:
In these times, we suggest you take only one carry-on and one "personal item" per person. Avoiding the hassle of baggage claim, customs and lost luggage is more than worth having to wear an outfit more than once, especially in such a laid-back environment.
Clothing/Shoes/Weather Gear: Swim shoes... sea urchin danger.
Toiletries and Medical Supplies: Rolling papers.
Miscellaneous: Make sure your cell provider serves Jamaica (most don't). Calls to/from Jamaica are very expensive.
Luggage and bags:
Bring a waterproof beach bag if you are going out on the water, things get wet when you are out on boats
Clothing/Shoes/Weather Gear: If you are planning on visiting any of the falls or wading out into the water (lots of sea urchins-ouch!), a pair of aqua shoes is a good investment.
If you are staying at an all inclusive, you should pack at least a nice pair of pants (men) and a skirt/sundress (women) if you plan on going to the reservation only restaurants.
A hat is also a good idea, the part on my head always burns and then peels
Sunglasses, bathing suit, sandals, tshirt
Toiletries and Medical Supplies: Sunscreen!!!! The sun is very intense in Jamaica, I get burnt if I'm out for even 15 minutes. Aloe is a good thing to have if you get burned.
Unless you are in a high end resort, don't assume they will have all the necessary toiletries. Our all inclusive had bath gel, shampoo, bar soap and lotion, no conditioner.
Camping/Beach/Outdoor Gear: Snorkel gear, most resorts will have it but it's nice to use your own mask and snorkel
Miscellaneous: I do a lot of reading on beach vacations, all the magazines I've not had the time to read or maybe that 700 page book that I've been meaning to tackle
If you are at an AI, bring along a water bottle or mug otherwise you'll be drinking out of tiny plastic cups or buying a mug at the resort.
Extra plastic bags come in handy for carrying home wet bathing suits or for packing a snack for excursions that leave before breakfast opens or a snack for the plane trip home
Bring lots of small bills for tips
Bring a water proof camera if you do any of the falls. You can get them away from tourist sites fairly cheap but if you try to buy them at a resort, etc. you might as well take out a loan.
Camping/Beach/Outdoor Gear: Reef shoes are a must have. Whether it be for getting around the beaches/reefs or scaling a set of falls.
Miscellaneous: Take as much cash as you'll need! I came a little short (thanks to a Chicago trip) and it took almost two days to get to an ATM.
Luggage and bags:
One (large, checked) suitcase with clothes, one (carry on) with camera and accessories, and something to tote stuff to the beach in.
Clothing/Shoes/Weather Gear: Bathing suits, shorts, and maybe one nice outfit to wear to Martinos or the Starlight grill.
Toiletries and Medical Supplies: Sunscreen, burn relief, headache relief (definitely not the place you want a headache), ear medicine (vinegar, peroxide, and alcohol mixture) if you are a diver.
Photo Equipment: I brought as much as I could stand. I started to bring only a small digital, but I am glad I changed my mind. I ended up bringing 2 SLRs and a digital, as well as Frank's underwater camera. On our jungle safari, I had one SLR with bw film, one with color, and interchangeable lenses, one wide, one zoom. I got some great shots being able to switch like that! This year when we go back I have added an underwater cover for my digital, so I hope to get some fish life to add to my album. PS BUY BATTERIES AND FILM IN THE STATES they are much cheaper at home!
Camping/Beach/Outdoor Gear: Hat & Sunglasses. No need for towels they were in great supply.
Miscellaneous: Bring A LARGE INSULATED CUP! Beverages come in smaller glasses and mean more trips from the beach to the bar. We filled ours full of ice and the great sweet tea most days, but many used their large cups as mini-kegs if you know what I mean!