This is how we'd do it. My rep would call me and throw out dates. We'd narrow it all down and decide. Then the client would go to the talent agencies in Dallas and cast "real people" as models for our shooting. We'd all hop on a charter and head down to the islands. Usually three model couples, a client representative, an agency representative, a make up person, a production assistant, my assistant and a gofer for the client. We'd hit the ground running and try to get as many set ups as we could in a seven day period.
One the evening before our last day in Jamaica we'd taken a break to savor a mixed drink and the sunset (we'd shoot the evening cabaret in an hour or so). That's when I looked up from the bar and saw our model walking along the beach, suffused by "magic hour" light and looking incredible. I grabbed the camera off my shoulder (I'm never without a camera---even if it looks dorky) snapped four frames and then the light changed. She found her boy friend and the serene look vanished. The moment was past. But I've always loved the image.
If you put down your camera you may miss the one unscripted moment that defines your idea of "vacation in paradise."