Travel light! Jamaica is a hot, tropical country and you shouldn't need much clothing. My motto is: if you can't take your main bag as a carry-on onto an aircraft, you've packed too much for a one-week visit. This depends on where you stay, however. The fancier the resort, the more you may need fancy clothes.
A duffel bag with zippered pockets is handiest, though small suitcases are also good. Garment bags are ideal if you plan on staying at one resort. It's best to avoid back packs with external metal straps. Make sure your luggage is padlocked before parting with it, and don't leave anything of value in external pockets. Theft from baggage at the Montego Bay airport is high. A small daypack is also handy.
Loose-fitting lightweight cotton clothing is best because it allows air flow in the hot humid climate. Tight clothing tends to make you sweat more and can get uncomfortable, as will synthetics like nylon. T-shirts and tank tops are the perfect wear for out-doors and are best worn untucked, allowing air to circulate. You are going to sweat!
White is the best color for reflecting the sun's rays, but gets dirty quickly. A long-sleeved shirt and long pants are useful in case you get a sunburn. You'll also need long pants for the more upscale discos and restaurants.
Don't forget one or two pairs of shorts, which can be your normaldaywear, and swimwear, which should be restricted to the beach. Dress more modestly in towns. This is particularly true of conservative Kingston, where women may attract unwanted attention commensurate with the amount of flesh they expose. Topless bathing even a birth-day suit) is allowed at some resort hotels and on the beach in Negril, but elsewhere is frowned upon and may even result in hostility from shocked locals.
A light sweater might prove handy at night - you'll certainly need one in the upland areas.
Some hotels require casual evening wear at dinner. Several of the ritzier hotels even require jackets (and ties in winter) for men, and elegant dresses for women while dining. Such hotels do not allow shorts or jeans in the dinning room. Elsewhere, however, fancy togs are taken more as a statement of the wearer's insecurities or snootiness. They also mark you as wealthy, leaving you more open to potential robbery or higher prices when bargaining for souvenirs.
Speaking of money its good idea to carry your cash in a money-belt beneath your clothing.
You'll get by with a pair of sneakers, sandals, or flip-flops (thongs), and a pair of lightweight casual shoes for evening wear. In the interest of conservation and for personal safety, you should refrain from walking on coral, but elasticated canvas and rubber 'reef walking' shoes are ideal for wading.
If you plan on hiking, prepare for variable weather conditions. Rain can fall at any time of year, especially in mountainous areas. Pack a waterproof jacket, a sweater, and ideally, a lightweight rain jacket. At lower altitudes, lightweight cotton clothing will suffice.
Toiletries and Supplies
You should bring all toiletries with you. but you don't need to overdo it. For example, you may find an excess of make-up is uncomfortable in the humid tropical heat. At a minimum, your basic kit should include toothpaste, toothbrush, dental floss, deodorant, shampoo, skin creams, make-up, tampons, contraceptives and a basic health kit.
Outside of villas, hotels resorts and medium size hotels, few hotels in Jamaica provide complementary toiletries. Don't forget a washcloth. Unless you are staying at an upscale hotel, consider bringing a beach towel. Better yet, buy one in Jamaica. You can also buy any toiletry you may need in Jamaica, although at higher prices in the hotels gift shop. Go to a local supermarket or grocery.
Don't forget a spare pair of sunglasses or contact lenses, and any medicines you may require. Pharmacies should be able to fill any prescriptions you require. Many drugs that are available by prescription only in the USA can be bought over the counter in Jamaica.
A flashlight is useful in the event of a electrical black-out (very common), or to find your way along unlit streets or paths at night. I also consider a Swiss Army knife is essential.
Other essentials include resealable plastic bags (handy for toiletries), a small laundry bag (for dirty underwear and wet clothes), a fold-up umbrella (which will also prove a handy parasol), plus a hat for shade (or buy a straw hat in Jamaica).
Its better to bring items such as laundry detergent, notepads, pencils and batteries with you; they are available in the major towns but don't rely on finding them when you want to buy them.
Self-service, coin operated laundries are as rare as the Mauritian dodo. Drop-off laundries are more widely available in major resort towns in Negril, Montego Bay, Kingston, Port Antonio and Ocho Rios Jamaica. Elsewhere local women may offer to clean your clothes.
Most hotels - though not all - can arrange next-day or two-day laundry. Usually they will send your clothes to be washed. For the better hotels, this will be to a professional laundrette. For more modest establishments, expect your laundry to be washed in a river and beaten over rocks (don't expect your clothes to be ironed....an additional charge).
Many establishments that advertise 'dry cleaning' don't use a chemical treatment. Often this means that your garment will be hand-washed in cold water. Be sure to check.