In 1982, while working as chief foreign feature writer for "The Sunday Times", Winchester was on location for the invasion of the Falkland Islands by Argentine forces. Suspected of being a spy, Winchester was held for three months as a prisoner in Ushuaia, Tierra del Fuego. He wrote about this event in his book, "Prison Diary", published in 1983 and also in "", published in 1985. That same year, he shifted to working as a freelance writer and travelled to Hong Kong. When Condé Nast re-branded "Signature" magazine as "Condé Nast Traveler", Winchester was appointed its Asia-Pacific Editor. Over the following fifteen years he contributed to a number of travel publications including "Traveler", "National Geographic" and "Smithsonian" magazine.