Luggage and bags:
Since we have been traveling by boat, we don't have any luggage. However when we fly, we take two carryon sized bags each. I check one of mine - I just don't carry any more than two small bags.
Clothing/Shoes/Weather Gear: A wide brimmed hat.
Toiletries and Medical Supplies: SUNSCREEN
Photo Equipment: I have always traveled with at least one camera. Now I have at least two. I have one digital and one film camera. (I still do not do well in a complete downpour or where I have to take a fast picture with a digital). At this site, photographs were forbidden indoors, and I had good luck with taking pictures through the windows. Bob is in the purple shirt walking away. I'm holding the camera down at chest level.
The website has some hints for travel picture taking.
Miscellaneous: Practice so that you can take pictures with your digital camera without using flash. Try taking pictures in a restaurant at home. Not only is a picture without a flash less intrusive (and more stealth like in this case where photos were forbidden), but the pictures are usually better because they are less washed out.
Photo Equipment: While in South Beach, keep your eyes open for Papparatzi, he'll snap you by surprise. Just kidding, guys. This gentleman was on photo assignment at SOBE from England. He was on his way to Key West. Bring your camera so you can take a piece of SOBE with you.