Money Tesla takes the top 2 spots: The 25 most expensive cars to insure June 29, 2019 Michael B. Sauter, 24/7 Wall Street Comments Off on Tesla takes the top 2 spots: The 25 most expensive cars to insure Those feeling as if they are paying more for car insurance are not wrong. Car insurance premiums rose by more than 20% between 2011 and 2018.