Other Investments - Schedule of Other Investments (Details) - USD ($) $ in Thousands	Dec. 31, 2019	Dec. 31, 2018
Investment Holdings, Other than Securities [Line Items]
Vessels, Net	$ 85,991	$ 50,125
Real estate, net	2,188	10,019
Other	28,588	14,858
Total other investments	137,472	75,002
Vessels, Accumulated Depreciation	3,817	898
Tiptree Insurance
Investment Holdings, Other than Securities [Line Items]
Vessels, Net	0	0
Real estate, net	2,188	10,019
Other	19,559	8,507
Total other investments	42,452	18,526
Tiptree Capital
Investment Holdings, Other than Securities [Line Items]
Vessels, Net	85,991	50,125
Real estate, net	0	0
Other	9,029	6,351
Total other investments	95,020	56,476
Corporate bonds, at fair value
Investment Holdings, Other than Securities [Line Items]
Other	20,705	0
Corporate bonds, at fair value | Tiptree Insurance
Investment Holdings, Other than Securities [Line Items]
Other	20,705	0
Corporate bonds, at fair value | Tiptree Capital
Investment Holdings, Other than Securities [Line Items]
Other	$ 0	$ 0