Cover Page - USD ($)	12 Months Ended
	Dec. 31, 2022	Feb. 21, 2023	Jun. 30, 2022
Document Information [Line Items]
Document Type	10-K
Document Annual Report	true
Document Period End Date	Dec. 31, 2022
Current Fiscal Year End Date	--12-31
Document Transition Report	false
Entity File Number	1-8993
Entity Registrant Name	WHITE MOUNTAINS INSURANCE GROUP, LTD.
Entity Incorporation, State or Country Code	D0
Entity Tax Identification Number	94-2708455
Entity Address, Address Line One	23 South Main Street, Suite 3B
Entity Address, City or Town	Hanover,
Entity Address, State or Province	NH
Entity Address, Postal Zip Code	03755-2053
City Area Code	603
Local Phone Number	640-2200
Title of 12(b) Security	Common Shares, par value $1.00 per share
Entity Well-known Seasoned Issuer	Yes
Entity Voluntary Filers	No
Entity Current Reporting Status	Yes
Entity Interactive Data Current	Yes
Entity Filer Category	Large Accelerated Filer
Entity Small Business	false
Entity Emerging Growth Company	false
ICFR Auditor Attestation Flag	true
Entity Shell Company	false
Entity Public Float			$ 3,569,108,224
Entity Common Stock, Shares Outstanding (in shares)		2,567,527
Documents Incorporated by Reference	Portions of the Registrant’s Definitive Proxy Statement to be filed with the Securities and Exchange Commission (“SEC”) pursuant to Regulation 14A under the Securities Exchange Act of 1934, as amended (the “Exchange Act”), relating to the Registrant’s Annual General Meeting of Members scheduled to be held May 25, 2023 are incorporated by reference into Part III of this Form 10-K. With the exception of the portions of the Proxy Statement specifically incorporated herein by reference, the Proxy Statement is not deemed to be filed as part of this Form 10-K.
Entity Central Index Key	0000776867
Amendment Flag	false
Document Fiscal Year Focus	2022
Document Fiscal Period Focus	FY
New York Stock Exchange
Document Information [Line Items]
Trading Symbol	WTM
Security Exchange Name	NYSE