Fleet in a dream may signify any type of transportation. It could indicate that you need to make changes to your lifestyle and the way you manage your life and time. You may want to use more public transport or get rid of the stress of owning a car altogether.
Dreaming about a fleet represents the feeling of being free and unconstrained, which could be both exhilarating and fearful at the same time. A fleet may also represent feelings of being lost, confused or abandoned by others. If you dreamed about seeing fleets on ocean waves, it would mean that you have these types of feelings about yourself.