A boat trailer and a method of backing up a boat on a trailer. The boat trailer includes a trailer back-up system having a first image capture device, a second image capture device, and a transmitter. The first image capture device is mounted on a left guide pole of the trailer in a rear-facing direction, and the second image capture device is mounted on a right guide pole of the trailer in a rear-facing direction. The transmitter is in communication with each of the first image capture device and the second image capture device and configured to transmit live video images from the first image capture device and from the second image capture device to a display device. The method includes moving the trailer with a boat loaded on the trailer in a rearward direction and capturing, in real-time, a first view and a second view.