Stephen grew up in England and graduated from Jesus College, Oxford in 1992 with a degree in history, securing a job with the Baltic Observer in Riga, Latvia, as assistant business editor. This included some reporting and led to his first travel piece, a classic entitled "Saaremaa Karma".

In 1995, after a year organising exhibitions in Vietnam and Myanmar for an eccentric Chinese millionaire, he returned to journalism, working for Basis Point, a Hong Kong-based financial news provider. After three years in Hong Kong, he spent two years running the Singapore office before taking a break in 1999 to travel around the world: the trip took in Zimbabwe, South Africa, Australia, New Zealand, the South Pacific and South America, and ended in Jordan and Israel.

In 2000 Stephen returned to Hong Kong and Basis Point, where he became Asia-Pacific Bureau Chief after the company was acquired by a New York-based subsidiary of Reuters, the following year.

After a couple of years commuting between an elegant 1920s villa in the former French Concession district of Shanghai, and cramped apartments in Hong Kong, he moved to Taipei, Taiwan in 2003. He spent three years in the city, half of that time dedicated to writing and researching the first Rough Guide to Taiwan. 

In 2006, after 12 years in Asia, Stephen moved to New York, and helped update the Rough Guide to Spain (chapters on Old Castile, Euskal Herria, Aragon and Catalunya) and the Rough Guide to Mexico (Veracruz and Chiapas & Tabasco). He also wrote sixteen pieces for the “ultimate travel experience” series – 25s – to mark the 25^th anniversary of Rough Guides, and researched miscellanies for the Islands, Wonders of the World, France and Italy books.

In 2007 he started researching the first Rough Guide to Puerto Rico, due to publish in the second half of 2008. He currently lives in New York’s West Village, in an apartment almost as tiny as his first place in Hong Kong.