There are insurance policies out there aimed specifically at young drivers (for example, Footman James' Classic Car Young Enthusiasts Policy). These typically offer a 5-10 per cent discount, but depend on various criteria being met. Some common examples of hoops to jump through are that the car has to be over 30 years old, a member of a selected car club, and that the insured driver must have access to another car. To find out about these policies, you'll need to pick up the phone and get some quotes - only then will you know if it's something you can afford. As for fitting a telematics 'black box' that collects driving data, these are generally only fitted to cars under 20 years old.