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Segment Reporting - Summary of the Schedule of the Company's gross written premiums based on the location of the insured risk (Details) - USD ($)
$ in Millions
12 Months Ended
Dec. 31, 2017
Dec. 31, 2016
Dec. 31, 2015
Segment Reporting Information [Line Items]      
Gross written premiums $ 3,360.9 $ 3,147.0 $ 2,997.3
Australia/Asia      
Segment Reporting Information [Line Items]      
Gross written premiums 167.3 140.5 140.0
Caribbean      
Segment Reporting Information [Line Items]      
Gross written premiums 17.6 14.3 20.3
Europe      
Segment Reporting Information [Line Items]      
Gross written premiums 94.5 109.7 113.6
United Kingdom      
Segment Reporting Information [Line Items]      
Gross written premiums 258.3 231.4 223.6
United States & Canada      
Segment Reporting Information [Line Items]      
Gross written premiums 1,729.3 1,597.0 1,479.5
Worldwide excluding United States      
Segment Reporting Information [Line Items]      
Gross written premiums 88.1 90.7 107.2
Worldwide including United States      
Segment Reporting Information [Line Items]      
Gross written premiums 868.6 837.2 793.6
Others      
Segment Reporting Information [Line Items]      
Gross written premiums $ 137.2 $ 126.2 $ 119.5