If you get to the Woodward Dream Cruise or any other car show and you don't care for the lighting conditions or surroundings, get close.
Most of the cars at the Cruise are packed together pretty close. This can be troublesome because you may not alway have the background you want, or another car is reflecting in your subject car. During a nice summer day the sun is straight up, a challenging lighting situation to make good looking shots.
When either of these situations happen, of if you want to give yourself a project, get in close. Pick an interesting part of the car. It could be a shape, a texture or an interesting reflection. Remove all the other options and just look for details.
In the bright sun handholding may be fine. In lower light situations, a tripod or mono-pod will be necessary for sharp images.