On pilgrimage with Simon Caldwell, Master of The Keys

Where would you go?

To Paraguay to visit the missions of La Santísima Trinidad de Paraná and Jesús de Tavarangue and whatever remains of the other missions founded by the Jesuits in the 17th and 18th centuries to rescue the Guaraní Indians from the lethal clutches of colonial slave traders. I would make this pilgrimage not on foot, but as far as possible on horseback – preferably on a Mangalarga Marchador, a breed developed by Brazilian ranchers using Arab, thoroughbred and American saddlebred bloodlines.

Would you make any special stops?

I would like to visit the Marian shrine of Caacupé, which Pope Francis declared a minor basilica after he said Mass there in 2015. Our Lady is revered there as "Our Lady of Miracles" following several inexplicable healings at her intercession. The shrine is one of the most popular and important pilgrimage destinations in South America.

Whom would you take?

A small group of fellow riders since horses, as herd animals, prefer company. I hope it might include Donna Tartt, the bestselling American author famous especially for The Secret History and The Goldfinch. I was fascinated to discover recently that she is a Catholic convert who in an essay called "The Spirit and Writing in a Secular World" – published 25 years ago in The Novel, Spirituality and Modern Culture, edited by Paul Fiddes – confessed that "faith is vital in the process of making my work and in the reasons I am driven to make it". I would love to know more.

You can transplant your favourite pub, bar or restaurant onto the route. What is it?

‍Because I like so many pubs I can't choose a favourite, but I'll plump on this occasion for Ye Olde Cheshire Cheese, the Fleet Street drinking hole frequented by GK Chesterton, Charles Dickens, Samuel Johnson, PG Wodehouse, Sir Arthur Conan Doyle, Alfred Tennyson and Mark Twain and generations of England's finest journalists. To my mind, it is one of the most atmospheric pubs in London. I particularly like Polly, the African grey parrot that lived in the pub for 40 years, and now sits stuffed behind the main bar.

Camp under the stars or find a church hall to sleep in?

Definitely camp under the stars. Gazing into the celestial void is somehow a spiritual experience, reminding me often of the times when my father would walk us to midnight Mass in the Christmases of my childhood and I would hurry along with my head up, mesmerised by the night sky. Stars were painted inside the domes of our Romanesque parish church, indicating Almighty God as the Creator of the universe who is infinite in all perfections.

Which books would you take with you?

I would take A Vanished Arcadia by RB Cunninghame Graham, the Scottish traveller and writer deeply admired by Joseph Conrad, which records the activities of the Jesuits in Paraguay between 1607 and 1767. Cunninghame Graham did not view Christianity favourably, and his prejudices come through in this work, yet he can only marvel at the sheer heroism of the Jesuits. The story of a single episode of violent resistance in this period inspired the 1986 film The Mission by Roland Joffé. Interestingly, A Vanished Arcadia identifies the man at arms as an Irish Jesuit called Thaddeus Ennis rather than Spanish Captain Rodrigo Mendoza, the role played by Robert De Niro in the movie.

What spiritual text would you ponder as you walked?

The Canticle of Creatures of St Francis of Assisi is the obvious choice for a pilgrimage by horseback through striking countryside.

What's your go-to prayer?

After Communion I often offer St John Henry Newman's incredibly beautiful prayer to the Sacred (and Eucharistic) Heart of Jesus, which concludes with the words: "Make my heart beat with your heart. Purify it of all that it is earthly, all that is proud and sensual, all that is hard and cruel, of all perversity, of all disorder, of all deadness. So fill my heart with you, that neither the events of the day nor the circumstances of the time may have power to ruffle it; but that in your love and your fear it may have peace."

What's the singalong to keep everyone's spirits up?

Moving from the sublime to the ridiculous, I'm going to have to say it would probably be "You're The One For Me, Fatty", by the brilliant and more-sinned-against-than-sinning Morrissey. I can't lie. I love this stuff. I'd sing it to my horse.

You're allowed one luxury – what is it?

A pair of binoculars so I can get closer to wildlife. I can lose myself for hours by simply watching birds.

What would you miss most about ordinary life?

My phone. But I'd make a point of leaving it behind. It has become a ball and chain and I'd be glad to be rid of it for a couple of weeks. A period of absence would be a difficult but refreshing interlude of detox – but I know full well that I will be hooked once more to my handset the instant I return to the rigours of 21st-century postmodernity. One can't help but sometimes wonder if life was much better before we all became addicted to digital disruption.

‍Photo: View of the facade of the Virgin of Miracles Basilica in Caacupe, 50 kilometres east of Asuncion, Paraguay, 7 December 2019. (Photo by NORBERTO DUARTE/AFP via Getty Images.)

Simon Caldwell is a journalist and novelist who has recently begun a three-year term as the Master of The Keys, the Catholic Writers' Guild founded by the circle of GK Chesterton. He is the author of The Beast of Bethulia Park (2022) and Lady Mabel's Gold (2025), both published by Gracewin.

This article appears in the September 2025 edition of the Catholic Herald. To subscribe to our thought-provoking magazine and have independent, high-calibre and counter-cultural Catholic journalism delivered to your door anywhere in the world click HERE.