Clothing/Shoes/Weather Gear Shorts, sandals, a swimsuit or 2, polarized sunglasses if you have them and a hat.
Toiletries and Medical Supplies Sunscreen...SPF 30+
Chicken repellant, if you can find some. ;-)
Photo Equipment Polarized lense for the water shots.
Miscellaneous Make sure to have Polarized sun glasses...the water looks Soooo much better without the glare that the Polarization cuts down.
Clothing/Shoes/Weather Gear A sexy bikini definitely is standard attire indoor and outdoor a lot of the times in Key West. The men wore their swimwear around the clock, it seemed. All you need is a t-shirt and flip flops. Ahh! The life....!!!
Luggage and bags Carry some clothes in you carry on bag, especially when travelling from a colder climate. Airlines are notorious for not getting bags onto planes from Miami to Key West, and you won't want to be lounging around in jeans when you get there. The good news: planes often come in only an hour or two apart and the airline delivers luggage.
Clothing/Shoes/Weather Gear Bring more bathing suits than you think you need, and don't go too heavy on the formal wear. Almost every restaurant in key west accepts diners in shorts and nice short-sleeved shirts. Also, bring water shoes if you're squeamish about rocks or plantlife on the ocean floor.
Photo Equipment Film is expensive in key west, so bring your own. If you must buy more, go to the Eckerd on Simonton, not one of the souveneir shops on Duval.
Clothing/Shoes/Weather Gear I'll just tell you what NOT to bring. No long sleeve shirts, pants, boots, sweaters, coats, or thermal underwear. In fact you can leave the socks home too. Swimwear, four pairs of shorts, five T-shirts, and all the undies you'll need for the time you'll be here and that's about it. Oh, and sunglasses.
Clothing/Shoes/Weather Gear Cruise
Toiletries and Medical Supplies Hey, don't forget the dramamine or whatever sea sickness medicine works for you.
Camping/Beach/Outdoor Gear Oh, and don't forget you bathing suit. Although Lisa is seasick, she is still looking good in her bathing suit. So remember that!
Luggage and bags Bring a backpack to carry your stuff especially if your on a scooter.
Clothing/Shoes/Weather Gear Thongs, a bathing suit, sunglasses
Toiletries and Medical Supplies Sunscreen, lotion, lip balm.