 Nyorai kupfuurira kweiyi ndima - Muna 1982, apo aishanda somunyori mukuru wezvinhu zvokumwe zveThe Sunday Times, Winchester akanga ari panzvimbo yokupinda muFalkland Islandsnemauto eArgentina. Achifungidzirwa kuva musori, Winchester akachengetwa kwemwedzi mitatu somusungwa muUshuaia, Tierra del Fuego. Akanyora pamusoro pechiitiko ichi mubhuku rake, Prison Diary, rakabudiswa muna 1983 uyewo mu, rakabudiswa muna 1985. Gore iroro, akachinja kushanda somunyori akazvimirira uye akaenda kuHong Kong. Apo Condé Nast akashandura Signature magazini se Condé Nast Traveler, Winchester akagadzwa mupepeti weAsia-Pacific. Kwemakore gumi nemashanu akatevera, akabudisa mabhuku akawanda anotaura nezvenzendo, anosanganisira Traveler, National Geographic, uye magazini inonzi Smithsonian. 