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.
Although valued with a net worth of £60million in the 2004 Sunday Times Rich List, as Sea Containers hit financial troubles, he resigned as Co-Chief Executive Officer from each of his companies in 2006.. He continued as a Director of Orient Express Hotels Ltd until retiring on 9 June 2011. He is now designated as Founder and Chairman Emeritus.
- 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.