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During the Second World War, Portugal remained neutral – but that neutrality turned the country into a very active stage for discreet meetings, behind-the-scenes manoeuvring, refugees in transit and spies from both sides of the conflict. Estoril, with its hotels, bars and casino, was at the centre of that world. It is no surprise, then, that Ian Fleming stayed at the Palácio in 1941, in a period that would help feed the creation of James Bond.
It is precisely this imaginary – somewhere between cinema, espionage, royalty and war – that serves as the starting point for Shadows & Spies: A Classic Film & Writing Retreat at Palácio Estoril, organised by the Milford Writing Institute in collaboration with film historian John DiLeo. The retreat takes place from 8 to 14 November 2026, at Palácio Estoril Hotel, and is designed for curious travellers, fans of classic cinema, history and writing, with a group limited to 30 participants and an application process through the Milford Writing Institute.
The idea is simple, but good: at night, participants watch classic Hollywood films shot in or inspired by Portugal; the following day, they head out to visit places connected to what they saw on screen. In other words, cinema stops being confined to a room and becomes a map. The list includes titles such as On Her Majesty’s Secret Service, partly filmed at Palácio Estoril, The Conspirators, described by the organisation as a kind of unofficial “sequel” to Casablanca, 36 Hours, Lisbon, The Boys from Brazil and Casino Royale.
Along the way, there will be conversations about 1940s Estoril, Portugal’s role as a transit point for refugees during the war and the movements of spies that made the region fertile ground for unlikely stories. The programme also includes visits to several well-known settings: Praia do Guincho, Fortaleza do Guincho, Sintra, Pena Palace, Belém, Jerónimos Monastery, Belém Tower, Lisbon and, of course, Casino Estoril. The week ends with a vesper martini, baccarat and the casino as the backdrop.
Writing is part of the plan too, of course. Throughout the week, participants will record their impressions of the films, places and experiences of the retreat. Those texts will then be developed with Richard C. Morais, founder of the Milford Writing Institute, and John DiLeo, and brought together in a digital magazine called Shadows & Spies: Classic Films and History in Portugal. All participants receive a byline as correspondents for the publication, and the best piece will be recognised with the first Cascais & Estoril Classic-Film Writing Award.
The prize includes, among other things, two return flights to Lisbon, two nights at Palácio Estoril Hotel and a private dinner with Bernardo Corrêa de Barros, president of Turismo de Cascais. The retreat itself costs €5300 or US$6100 per person in a single room, and €4950 or US$5700 per person in a double room, including accommodation, meals included in the programme, activities, excursions, transport during the week, workshops, editorial guidance and preparation of the digital magazine.
Palácio Estoril Hotel, Estoril. 8-14 Nov 2026. Maximum group of 30 participants. Applications through the Milford Writing Institute