Luggage and bags:
Once you make it you never have to do it again! The less you pack, the less you carry.
Clothing/Shoes/Weather Gear: It is HOT! Key West is very casual!
Toiletries and Medical Supplies: SUNBLOCK, (48SPF) SHOULD DO IT!
You will STILL tan!
Photo Equipment: You will need lots of batteries and a laptop to download to is always nice.
Camping/Beach/Outdoor Gear: You can camp on the beach in some places!
Luggage and bags:
You can go with the expensive stuff or you can use good old trustworthy ziplock bags (if you puff them up with air...they float!). Someone will convince you to go snorkelling or kayaking and no one likes wet cigarettes, lost keys, or a sunken wallet (except divers).
Clothing/Shoes/Weather Gear: bring 1 set of real clothes in case you want to go out for a nice evening; bring flip flops, tank tops, and shorts, in case you don't.
Toiletries and Medical Supplies: If you get bit by a sea anemone, pee on the sting. Really. Old Bahamian remedy. It will loosen the micro-stingers and they will fall out.
Bring aloe. Bring neosporin. Be careful of fire ants and crazy bugs that are seasonal to the tropics.
Photo Equipment: Waterproof camera, obviously. Oh, but you may think you'll never need a flash. How about when your friend passes out in a bowl of pretzels and you get the locals to pose with him at the bar? You'll want that one with a flash...
Camping/Beach/Outdoor Gear: Bring a sleeping bag. You never know who's house (or beach) you may get to stay at.
Miscellaneous: Beer googles and an extra liver couldn't hurt. Some big, heavy duty plastic bags are always useful when you have wet clothes that need to get packed with the dry ones. It happens.
No matter how much you get out in the sun where you live, bring a hat, long sleeved shirt (if you are going fishing) and sunscreen . . . I am a sun worshiper, but the sun here is like nothing I have ever experienced
Toiletries and Medical Supplies: Sunscreen
Camping/Beach/Outdoor Gear: Cool, casual to dressy-casual clothing . . . If it makes you happier, go ahead and bring one really dressy outfit . . . I bet you won't use it
Toiletries and Medical Supplies: Sunscreen everything! If your going to be out on a boat all day it might be a good idea to take some motion sickness stuff. I dont normally get ill from that, but I did this time and it kinda puts a damper on your day.
Photo Equipment: Underwater cameras!!!
Wear comfortable clothes! It's warm in Key West so I recommend shorts, t-shirts, sandals (or tennis shoes), a hat, and sunglasses
Toiletries and Medical Supplies: Sunblock and Lip Balm
Photo Equipment: Do not forget your camera! If you are going scuba diving or snorkeling, get an underwater camera so you can remember how beautiful the reefs are!