5. Mercedes S550 convertible
- Average cost to insure: $3,502
The S550 convertible is a member of the S-Class family, but its beautiful bodywork has little in common with the stately sedans. A luxury drop top, the S550 features virtually every safety and tech feature Mercedes has to offer. Its twin-turbo V8s and available V12 are no slouches either. In “base” S550 trim, the massive convertible can go from zero to 60 in just 4.9 seconds. That combination of speed, luxury, and its relatively recent debut (it’s a new model for 2017) makes the S550 a handful to insure. If you’re thinking about buying one, expect to pay around $3,502 a year for insurance.
4. Maserati Quattroporte GTS
- Average cost to insure: $3,547 a year
For the past 55 years, the Maserati Quattroporte has been one of the most striking sedans in the world. Even if its name is laughably bland — it literally means “four doors” in Italian — and its styling has been hit or miss over the years, its sumptuous interior and glorious V8 engine has always made it an irrational favorite among the well-heeled. But Maseratis are notorious for reliability problems. Mechanical failures and a lot of speed (the current car is available with a 523-horsepower V8) make them a headache to cover. Owners spend an average $3,547 a year insuring their Quattroportes.
3. Mercedes-AMG S63 4Matic convertible
- Average cost to insure: $3,624
Take all the reasons why the aforementioned S550 was expensive to insure, and add to it the romper-stomper style of driving that the S63 convertible invites. In the hands of AMG, the S-Class convertible becomes a 577-horsepower, 2.5 ton rocket that can scramble from zero to 60 in 3.7 seconds. Is it any surprise that the S63’s combination of high-end luxury and world-class speed makes it expensive to insure? Buyers can expect to pay an average $3,624 a year for the privilege.
2. Dodge Viper GTS
- Average cost to insure: $3,779
After 25 years as one of world’s most outrageous car the Viper is gone after 2017, and it doesn’t look like it’s coming back. For its final year, the Viper was powered by a 645-horsepower V-10, tucked away under its long, sinuous, largely hand-formed hood. The car’s tendency to oversteer, as well as its number of expensive parts and dwindling parts supply, makes taking care of a damaged Viper a handful for insurance companies. Owners pay an average $3,779 a year on insurance.
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Mercedes-AMG S65 convertible
- Average cost to insure: $3,835
When it comes to expensive-to-insure cars, Mercedes is king. And the S65 has all the red flags that have already been highlighted by its stablemates on the list. Convertible? Check. Tuned by AMG? Check. Ridiculously expensive and brutally fast? Thanks to its $255,000-and-up price tag and 621-horsepower twin-turbo V12 engine, check. Owning the fastest and most exclusive convertible Mercedes makes doesn’t come cheap. As for insurance, that’s at least another $3,835 a year on average.