Churchill’s Madeira: A Statesman’s Palette of Rest and Paint

Introduction

On a January morning in 1950, the normally quiet fishing village of Câmara de Lobos found itself at the centre of an unexpected media frenzy. Colourful fishing boats bobbed in the small harbour, the scent of poncha and fresh black scabbard fish filled the air and, on a terrace overlooking the bay, a stocky English gentleman set up an easel and lit a cigar. The visitor was Sir Winston Churchill, the wartime Prime Minister who had steered Britain through the bleak years of the Second World War. Less than five years after leaving Number 10, Churchill was on the Atlantic island of Madeira to recharge his spirit and work on his war memoirs. He also hoped to indulge his hobby of painting en plein air. Within a few hours he had immortalised the fishing harbour of Câmara de Lobos on canvas, an act that would forever tie his name to the village and spark a tourism legend.

Churchill’s connection to Madeira was brief yet significant. He visited the island twice, first as a young war correspondent in 1899 and again half a century later as a Nobel Prize‑winning elder statesman. Both visits reveal something about his character: the restless adventurer traversing the globe in search of stories, and the mature politician seeking tranquillity, good wine and the therapeutic joys of painting. This article traces Churchill’s Madeiran journeys—where he stayed, what he did and the lasting impact his presence had on the island—while blending historical facts with the wit and humour that coloured Churchill’s own life.

Did you know?!

This Article is part of our Self-Guided-Tour
“Câmara de Lobos Walking Tour”

Check out the Self-Guided-Tour

A youthful stopover (1899)

Winston Leonard Spencer Churchill’s first encounter with Madeira occurred when he was only twenty‑five. In October 1899 he boarded the Union‑Castle liner Dunottar Castle bound for Cape Town. The young adventurer was sailing to South Africa to cover the Boer War for the Morning Post and simultaneously seek a parliamentary seat. En route the liner called at the port of Funchal. In his autobiographical My Early Life, Churchill recalled that the voyage had been rough and that “we dropped completely out of the world” because ships at that time lacked wireless communication. He wrote a letter to his mother describing seasickness and complaining that he had been “grievously sick”. The stop in Madeira was brief; he did not set foot on the island for any length of time nor record impressions beyond his discomfort. Nevertheless, the experience introduced him to the mid‑Atlantic outpost that would later feature in his leisure plans.

During the ensuing fifty years Churchill’s life took him to battlefields, the halls of Parliament and the top echelons of world power. Madeira lingered in the back of his mind mainly through its wines. Churchill relished Madeira’s fortified vintages and once delighted guests by observing that a bottle they were drinking had been laid down while Marie Antoinette was still alive. In his History of the English‑Speaking Peoples he recounted the legend of the Duke of Clarence being drowned in a butt of Malmsey wine, remarking, “Why should it not be true? At any rate no one has attempted to prove any different tale”. The island thus existed for him as both a place of myth and a source of liquid pleasure.

Planning the great escape

After the Second World War, Churchill led the Conservative opposition while working on his multi‑volume memoir The Second World War. The strain of politics and writing weighed heavily on him. To recuperate, he sought a warm retreat where he could bathe, paint and enjoy flowers. On 19 November 1949, he sent a telegram to Bryce Nairn, the British consul in Madeira, asking about “warm, paintable, bathable, comfortable, flowery, hotels etc.”. Churchill wanted secrecy; he and Clement Attlee were engaged in political sparring at home, and he hoped to slip away unobserved. Nairn responded enthusiastically and recommended Reid’s Palace Hotel, a storied property perched above Funchal Bay.

The winter of 1949–50 proved the right moment for a break. Churchill planned to combine relaxation with work on The Hinge of Fate, the fourth volume of his memoirs, and to practise his painting. He assembled a party comprising his wife Clementine, his daughter Diana, literary assistant Colonel Bill Deakin, secretaries Jill Sturdee and Elizabeth Gilliatt, and two Special Branch detectives for security. The prospect of having the “Churchill circus” descend on Madeira excited local officials, hoteliers and wine merchants, who prepared to greet the famed statesman.

Arrival on a tropical New Year

On 1 January 1950 the Union‑Castle liner Durban Castle steamed into Funchal’s harbour. Crowds lined the pier to watch as Winston and Clementine Churchill disembarked, accompanied by Diana and the rest of the entourage. Photographs from the Madeira Photography Museum show local dignitaries flanking the British guests. Islanders, grateful for Britain’s wartime leadership and charmed by Churchill’s global reputation, gave him a hero’s welcome. The British politician later mused that although he had been honoured by many people for whom he had done something, he had “never in my whole life been greeted with such enthusiasm by people for whom I have never done anything”.

The Churchills were whisked up the hill to Reid’s Palace Hotel. The hotel, owned by the Blandy wine family, was already legendary for hosting aristocrats and celebrities since its opening in 1891. From their suite on the first floor—today known as the Churchill Suite—the visitors enjoyed panoramic views of Funchal and the Atlantic. Reid’s staff treated them like royalty; when Churchill and his wife entered the dining room, other guests stood and applauded. Complimentary bottles of Blandy’s Madeira wine awaited them. The aged statesman settled into a routine of dictating his memoirs in the mornings, strolling through the hotel gardens and reading on his balcony in the afternoons.

A Rolls‑Royce to Câmara de Lobos

Within a few days the call of the canvas became irresistible. Churchill had brought dozens of paint tubes and was eager to capture the island’s light. On 5 January 1950—some sources state the 8th—he set out to find the perfect vista. The Leacock family, prominent wine merchants, supplied a grey Rolls‑Royce with driver to transport him and his equipment to Câmara de Lobos, a fishing village about seven kilometres west of Funchal. The road wound along banana‑covered slopes and vine terraces. Locals later joked about the spectacle of a stately limousine manoeuvring over cobbled tracks more accustomed to donkey carts.

Câmara de Lobos, whose name means “Chamber of the Sea Wolves” because early sailors saw monk seals lounging on its rocks, instantly enchanted Churchill. Colourful xavelhas (traditional fishing boats) were pulled up on the beach. Small white houses clung to the hillsides, and fishermen mended nets or drank poncha in the taverns. On the eastern side of the harbour stood the Espírito Santo viewpoint, a terrace overlooking the entire bay. Churchill chose this spot, set up his easel, donned his sun hat, lit his cigar and began sketching. Photographs taken by local photographer Raul Perestrello show him concentrating on the canvas while a detective holds an umbrella to shade him. His equipment appears almost comically excessive, with scores of paint tubes scattered on the table—a reminder that the great man travelled with every possible pigment.

The “Fishing Port of Madeira”

The result of this session was an oil painting entitled “Fishing Port of Madeira (Câmara de Lobos)”. The painting portrays boats with blue and red hulls floating before a sleepy village under steep hills. A dramatic escarpment rises behind white cottages with terracotta roofs and green shutters. The work conveys Churchill’s admiration for simple communities and his fondness for Mediterranean light. He later presented the painting to his son Randolph; it passed through the family and remains a cherished heirloom.

Churchill produced more than 500 paintings over his lifetime, most depicting scenes in England, France or Morocco. Madeira provided a new palette with lush greens, turquoise waters and dramatic cliffs. Painting, which he had taken up in middle age to combat depression, offered him a “joy ride in a paint‑box” and revived his spirits after the stresses of war. Although he never achieved professional acclaim, he exhibited under the pseudonym “Charles Morin” and donated works to charity. The Madeira canvas thus belongs to a personal narrative of art as therapy.

A holiday cut short

Churchill’s idyll did not last. On 10 January 1950 news reached him that Prime Minister Clement Attlee had called a general election for 23 February. With Parliament dissolved and the Conservative Party scrambling to prepare, Churchill felt duty bound to return to London. He reluctantly packed up his paints, leaving one finished canvas behind. On 12 January 1950 he boarded an Aquila Airways flying boat and departed from Madeira. He telegraphed Clementine, who stayed on with Diana, complaining that back home there would be “nothing but toil and moil”. The islanders showered him with gifts of Madeira wine to take back to England.

Statues, hotels and storytelling

After Churchill’s departure, the spot where he painted became a pilgrimage point. Locals renamed the Espírito Santo terrace the Winston Churchill Viewpoint in 1963. A bronze statue of the statesman with easel and cigar now sits on the platform; visitors pose next to an empty chair designed for selfies. Below the viewpoint, a restaurant called “Churchill Restaurante” displays a plaque marking the place where he set up his easel.

In later decades, entrepreneurs capitalised on the story. A boutique hotel opened on the site of Câmara de Lobos’ former fish market in 2019 and was christened the Pestana Churchill Bay Pousada. It features a sculpture of Churchill and reproductions of his painting, ensuring that guests learn the story as soon as they check in. Local guides lead visitors through the village’s narrow lanes, pointing out murals made from recycled cans, bars where poncha is crafted and the viewpoint where Churchill painted, weaving tales of a Rolls‑Royce on cobbles and a British leader charmed by a fishing community.

Promoting a legendary hotel and tasting local flavours

Churchill’s 1950 holiday carried an unexpected mission: he was effectively a walking advertisement.  In the early days of January that year, Reid’s Palace Hotel had only just reopened after the privations of the Second World War.  The managers seized upon the idea of inviting Britain’s most famous politician to help relaunch the grand old property.  As travel writer Ingrid from Travel Potpourri later recounted, no one quite knows how the hotel learned of Churchill’s southern escape, but staff raced to prepare for him and even borrowed furniture from wealthy Madeiran families to furnish his room.  Churchill’s presence generated press coverage that money could never have bought; photographs of him sipping tea on the terrace and strolling through the subtropical gardens appeared in newspapers across Europe.  He spent nearly two weeks at Reid’s, painting in the mornings and dictating his memoirs in the afternoons, and would have stayed longer if a snap general election had not recalled him to London.  His short stay nonetheless restored the hotel’s reputation as the place to be for royalty and celebrities.

The legend of Churchill also inspired modern entrepreneurs.  When the municipality converted the old fish market into the Pestana Churchill Bay Pousada in 2019, the intention was not simply to add another boutique hotel but to weave a narrative around the man with the cigar.  The Pousada’s manager, Célia Marques, told the magazine Essential Madeira that travellers are increasingly seeking smaller, more intimate properties and that the hotel’s terrace overlooking the fishing boats captures exactly the view Churchill painted.  Sculptures and reproductions of his canvas adorn the lobby and many of the fifty‑seven rooms, and the bar serves cocktails with names like “The Statesman”.  This purposeful storytelling has helped ensure that visitors associate Câmara de Lobos with art, history and hospitality.

Yet the village’s culinary scene remains anchored in traditions far older than Churchill.  According to Essential Madeira, the fishermen’s drink poncha originated in Câmara de Lobos; sailors mixed sugar‑cane rum, honey and citrus juice to ward off the chill of Atlantic mornings.  The concoction spread across the island and today is sold in lively bars such as Agrela, where bartenders still whip it in a wooden muddler and serve it with a plate of fried catfish, known locally as the “codfish of Câmara de Lobos”.  In 1985 another drink, Nikita, was invented at the Farol Verde pub when the owner experimented with pineapple ice‑cream, beer and white wine; the cocktail took its name from an Elton John song popular at the time.  These drinks add a light‑hearted twist to the narrative: while Churchill may not have downed poncha or Nikita during his painting session, modern visitors can toast to him with both.

Strolling through the village reveals further layers of history.  Câmara de Lobos is one of Madeira’s earliest settlements; it was founded in the 1420s on lands granted to explorer João Gonçalves Zarco.  The mother church bears Zarco’s coat of arms, and nearby the Press Museum—housed in the basement of a contemporary library—displays nineteenth‑century printing presses.  Bars now fill the waterfront where grocery stores once stood, a transformation chronicled by Juvenal Fernandes, the octogenarian proprietor of Barbearia Eva.  In an interview with Essential Madeira, he reminisced that when he was a boy the bay was lined with shops selling salt cod and barrels of wine.  Today the same spaces serve poncha and Nikita to tourists, but the barber insists the “street continues bustling”.  His century‑old barbershop, decorated with antique furniture and watched over by two parrots that greet customers with a cheeky “Olá!”, offers a humorous contrast to the sleek Pousada and reinforces the theme that modern tourism coexists with enduring local life.

Reflections on art and leisure

Churchill often joked that painting and writing were the only occupations in which he could lose himself entirely. After the disastrous Gallipoli campaign in 1915 forced his resignation as First Lord of the Admiralty, he took up painting as therapy. Art historians describe his style as impressionistic, favouring bold colours and loose brushstrokes. He preferred to work outdoors in warm climates and light similar to Madeira’s. During his stay he composed letters about seeking “paintable” scenes and requested additional tubes of paint upon returning to London. This small island thus became part of his lifelong search for light and colour.

Wine and hospitality also figured prominently. At Reid’s Palace he sampled aged Sercial, Bual and Malmsey wines and visited the Madeira Wine Lodge, a 17th‑century monastery now housing the Madeira Wine Company. Letters displayed there include his notes thanking the company for gifts of wine. He joked about the Duke of Clarence being drowned in a butt of Malmsey and acknowledged the islanders’ generosity when he returned to campaign. Local lore holds that he tasted poncha, the fishermen’s cocktail of sugar‑cane rum, honey and citrus, although there is no record of him drinking heavily on that January afternoon.

Legacy and memory

Although Churchill spent less than two weeks on Madeira, his visit left an indelible mark on the island’s cultural landscape. His painting became an emblem of Câmara de Lobos and appears on postcards, hotel wallpapers and guidebook covers. The viewpoint and Pousada ensure that his name remains synonymous with the village. Tour guides recount his astonished remark about being greeted with such warmth, emphasising the reciprocal affection between the statesman and the villagers.

For Madeira, the Churchill connection bridges local tradition with international recognition. It highlights the charm of small communities, the therapeutic value of art and the enduring appeal of island landscapes. It also reminds visitors that even world leaders need respite, and that a few days with a paintbrush and a glass of Madeira can create memories that last generations. Standing at the Winston Churchill Viewpoint, gazing over the same harbour he painted, one can almost smell the mix of oil paint and salt air, hear fishermen chatting and feel the rustle of banana leaves.

Conclusion

Sir Winston Churchill’s visits to Madeira bookend an extraordinary life. The first, in 1899, was a fleeting stopover that left little impression beyond a bout of seasickness and a taste of Madeira wine. The second, fifty years later, was a joyous escape for an ageing statesman seeking warmth, beauty and a break from politics. During those twelve days he wrote sections of his war memoirs, soaked in the sun at Reid’s Palace, sipped vintage wine and—most famously—painted the bay of Câmara de Lobos. His painting captured not only a scene but also the spirit of a community, and in doing so he unwittingly sparked a tourism legacy.

While Churchill never returned to Madeira, the island has never forgotten him. The bronze statue above the harbour, the hotel that bears his name and the stories told by guides and bartenders all testify to the power of a single visit. For modern travellers, retracing Churchill’s steps offers more than just a brush with history. It provides a window into the interplay between place and person, the healing power of art and the timeless charm of a sun‑drenched Atlantic island.