1. Mercedes-Benz S65 AMG Cabriolet: $3,835

Costing more than three times what it takes to cover a Honda Odyssey to insure, the top open-top version of the top-of-the line Mercedes-Benz S-Class is, well, over the top with its hand-built 6.0-liter twin-turbo V12 engine under the hood. It’s $250,000 base sticker price alone would warrant outrageous premiums.