Having automated systems on planes, in trains, or in cars, would both be more efficient and be safer. Cars being able to talk to each other would dramatically reduce car crashes. Planes with automated pilots would cease pilot error due to fatigue. Automated trains would behave similar to electric circuits.
The transportation industry is already investing in driverless cars and pilotless aircraft. Without a doubt, these two ideas will soon be realized. Google is currently experimenting with a driverless car, and the technology exists to make such a thing widespread. A few more years will be necessary for testing and refining, though.
For one thing, the technology that would allow there to be driverless cars and pilotless aircraft is not there yet and needs a lot more development. For another thing, most people would be afraid of such things, and it is going to take a lot of time before it can be introduced on a mass scale.
I could see things headed that way, but I don't think it's feasible in the near future. As with anything new it would have to be tested immensely before it could be put into the mainstream. There would be many issues and kinks to be worked out before it was available to the general public.
The transportation industry is not likely to make the transition to driverless cars and pilotless aircraft in the near future. There are already cars that park themselves but I think we are far from achieving a driverless car and pilotless aircraft anytime soon. There still needs to be production of such vehicles and it may happen.