Sherwood grew up in Lexington, Kentucky and earned a degree in economics from Yale University. Sherwood learned about shipping first in the U.S. Navy, spending three years as a cargo officer, and then working for U.S. Lines and CTI for six years.
In 1965, Sherwood founded Bermuda based, New York Stock Exchange listed, London headquartered shipping company Sea Containers Ltd with initial capital of $100,000. Over forty years Sherwood expanded Sea Containers from a supplier of leased cargo containers, into various shipping companies, as well as expanding the company into luxury hotels and railway trains, including the Venice-Simplon Orient Express and the Great North Eastern Railway franchise from London, England to Edinburgh, Scotland.
- James B. Sherwood, Ivan Fallon: Orient Express: A Personal Journey (2012) ISBN 9781849541879
- Latest Ferry News - November 2005 Archived October 10, 2006, at the Wayback Machine.
- Sea Containers Ltd. - Company History Funding Universe
- Grice, Elizabeth (27 April 2012). "James Sherwood interview: the man who relaunched the Orient-Express". The Daily Telegraph. London.
- Sunday Times Rich List 2004 - James Sherwood Times Online
- Sherwood to hand over helm at Sea Containers Telegraph, 8 December 2002
- "Dr Shirley Sherwood to Guest Curate Botanical ArtExhibition". Orient Express. 18 January 2005. Retrieved 25 March 2010.