How to travel like a British celebrity in Cuba - the must-do’s

Prince Charles and the Duchess of Cornwall Camilla visited Cuba in march 2019 as the first members of the royal family to land in Havana after the 1959-revolution. The royal couple visited Old Havana, drove a classic car to the Lennon Park, and prepared their own mojitos at a local restaurant. Before them, Edward of Windsor, Winston Churchill, Paul McCartney and Mick Jagger also jumped at the opportunity of visiting Cuba.

What were they eager to see and what did they do? Read on to find out.

Edward and Wallis Simpson, Dukes of Windsor

Seventy years before his grand-nephew, Edward VIII (1894-1972) chose Cuba as a tropical oasis of discreet glamour with his wife, the American actress Wallis Simpson. The then Duke of Windsor was running from the uncomfortable limelight that followed his abdication on 1936 to marry Simpson. They travelled to Havana four times, between 1944 and 1955.

  • Presidential Suite at Hotel Nacional de Cuba

    Hotel National de Cuba

    The Caribbean island offered them music, sea views from their hotel balcony and an endless summer – he was usually photographed in light-coloured guayaberas (a loose shirt with stripped seams that is traditional to the island) and got to mingle with Havana’s élite society who invited the royal couple to frequent parties.

    The Hotel Nacional de Cuba, inaugurated in 1930 as Cuba’s most impressive hotel, hosted them all four times in the Presidential Suite that included a private entrance and diner, plus areas to receive guests.

Churchill – 21st birthday in 1895 and out-of-duty Prime Minister in 1946

Wiston Churchill in two different moments of his life

Winston Churchill visited Havana in 1895 and in 1946, in what his biographers describe as two very different moments in his career.

In 1895, young second lieutenant Winston travelled on his first trip outside northern Europe as a war correspondent with almost no experience, turned 21 in the midst of the second Cuban pro-independence war (1895-1898) and gained his first medal for bravery under fire while developing his notoriety in the press.

Fifty years and a month later, Prime Minister Churchill took two months off out of his busy agenda and accepted an invitation from a friend in Florida, United States. It was the beginning of 1946.

  • Havana – Hotel Inglaterra and Hotel Nacional

    Young Winston and his friend Reggie Barnes stayed at Hotel Inglaterra in November 1895, facing Havana’s lively Parque Central. The Inglaterra, founded in 1875, has always been a favourite among celebrities, including the Russian ballerina Anna Pavlova, the French actress Sarah Bernhardt, and the famous matador Luis Mazzantini.

    In February 1946 however, PM Churchill was invited to stay with his wife Clementine and his daughter Sarah at the glamorous Hotel Nacional de Cuba. With a matchless view over Havana’s malecón seadrive, the Nacional also worked as a headquarter for meetings he held with the island’s authorities, although he wasn’t on an official visit.

    Read more about our favourite high-end accommodations in our blog Where to stay in Cuba

  • Cigars: "they quietly improve my temper"

    Wiston Churchill posing with a Cuban cigar

    Churchill had a documented relationship with cigars, showing up repeatedly in public with a smoky one in his hand. But when he came to Cuba in 1946 luxury imports were forbidden in post-war England, so he received a lot of queries about the relaxation of the regulation for Cuban cigars to be exported to the sister island sooner rather than later.

    Read more about Cuba's famous cigars at our post on Cuba, Cigars and Churchill

    At the first informal dinner at Hotel Nacional de Cuba, he was given the present of 500 Romeo y Julieta cigars, his favourite brand. The room, fully packed with thousands of admirers and press correspondents, observed the PM’s expression of subtle joy when accepting the gift.

    He didn’t visit Pinar del Río, Cuba’s best cigar-producing region, but he was nonetheless named as its Favourite Son. He did though make a stop at a cigar factory in Havana and explained then that "I simply enjoy (cigars), they quietly improve my temper."

    Moreover, many historians quote that he bluntly specified: "Cuba will always be on my lips", and if you take a look at his most famous portraits, you can see that he was being serious.

    Don’t miss out on Pinar del Río’s famous tobacco lands like Churchill did and discover the best of Cuba including Viñales’ worldly-admired tobacco trails

  • Palacio Presidencial – now Museo de la Revolución

    Vintage american cars parked in front of Museo de la Revolucion in Havana

    On his 1946 trip, even when he wasn’t visiting in an official capacity, Churchill was taken to the Versailles-inspired Palacio Presidencial, where he had a twenty-minute talk with Cuban president Grau San Martín. Right outside the palace, an animated crowd cheered Churchill, and he felt compelled to salute them with a final "Viva la Perla de las Antillas!" (Long live the Pearl of the Antilles!).

    The now Museo de la Revolución is on most travellers’ bucket lists for Cuba, as it houses permanent exhibitions documenting the island’s independence struggles from the 19th century up to the present day. But the real trait lies in admiring its grandiose halls featuring yellow marbles, innumerable mirrors, and an elaborate chandelier brought here by New York’s Tiffany’s in 1923.

    Watch our exclusive Q&A’s with Sir Cliff Richard when he visited this Museum. Check his personal tips for a Cuba holiday on our highlighted stories at Instagram @cubadirectholidays

  • Sun-kissed Varadero beach

    Turquoise waters and powdery sands in Varadero beach

    After three days in hectic Havana, Churchill and his family went for two days to Varadero beach, 87 miles to the east of the capital, where they enjoyed a sea-and-sand resort, which allowed them to relax while enjoying greater privacy.

    A 13-mile-long peninsula with white sands and clear sparkling waters, Varadero is Cuba's top beach destination. Regularly paired with Havana and Trinidad as part of our combo holidays, Varadero is a paradisiacal place to unwind after a busy spell of sightseeing.

Paul McCartney – impromptu visit in January 2000

Paul McCartney with locals during his trip to Cuba in January 2000

Although there are many overlapped testimonials regarding the ex-Beatle’s visit to Cuba, something is for sure: no one expected his private air-plane to land in Santiago de Cuba’s airport on a normal day of January 2000. He asked for permission to descend on a short visit, and no one could believe it once the plane landed and a hat-and-glasses McCartney said Hello to the locals.

  • City touring Santiago de Cuba

    Paul came accompanied by his girlfriend Heather Mills and two of his sons, and the whole group toured the city centre of Santiago, admiring the Parque Céspedes, the city’s Cathedral, the Moncada barracks, and the historic site at the San Juan hill.

    Founded in 1515, Santiago de Cuba is the heart of Cuba’s Caribbean culture, mixing the roots of African influence with Spanish colonialism like no other city in Cuba. It also boasts of the Sierra Maestra’s verdant mountains, intertwined with rivers and hidden communities.

  • Playing at Casa de la Trova Pepe Sánchez

    A curious McCartney was also spotted in the famous Casa de la Trova Pepe Sánchez, a lively music centre in the heart of the city, where he partook with the local musicians effortlessly playing the Cuban clave (leading rhythm) as if he were part of the band.

    Before leaving, he and his family bought a handful of CD’s, including some of Benny Moré and of the Grammy-awarded Eliades Ochoa. His sons got a selection of popular Cuban bands like Los Van Van, the Orquesta Aragón, Adalberto Álvarez y su Son and the NG, la Banda.

  • Castillo de San Pedro de la Roca

    Note written in Spanish by Paul McCartney during his visit to Santiago de Cuba in January 2000

    Finally, the McCartney’s had lunch at Castillo de San Pedro de La Roca, a 17th-century fortress with fantastic views over the Santiago bay. There’s a rather creepy statue of the ex-Beatle here today, a great spot to take a bizarre selfie. However, it does look like the family had a great time eating mixed vegetable omelettes, pineapple juice, local beer and chocolate ice-cream.

    Read more about Cuba's culinary highlights in our blog Unmissable Drinks and Dishes in Cuba

Mick Jagger – rolling in Havana in 2015 and 2016

The legendary rock star came on a paparazzi-free trip to Havana with his sons in October 2015, in what many newspapers described as the preparations for the historic concert the Rolling Stones gave for free in Havana on March 2016.

Documented in Havana Moon, the show was the biggest act to play Cuba since its 1959 revolution, and happened just three days after US President Barack Obama came on an also historic visit.

In his social media feed, Jagger posted a photo wondering around Old Havana with a light blue shirt and a messy hair, and captioned it with a simple "On a break in Cuba".

  • Music lead the way

    While on his first short break in Havana, Mick stayed at Meliá Habana hotel, and visited the Fábrica de Arte Cubano, the multifarious cultural centre hosted by Cuban musician X Alfonso. He was also spotted cruising through the streets in a classic American car and visiting music record studios with fellow local artists.

  • Dancing at a nightclub in the city

    The leading voice of the Rolling Stones accepted the selfie with the workers at Sangri La, a nightclub in Havana where he was seen dancing the night out as only he knows, with swag movements and true joyfulness.

    For a detailed overview of Havana’s nightlife scene, read more in our blogs Havana's 9 Dreamiest Rooftop Bars and Queer Cuba: The Ultimate Guide For LGBT+ Travellers

  • Enjoying the food scene too

    Following in the steps of the crème de la crème who had visited Cuba before, Mick Jagger ate at La Guarida, a restaurant housed in one of the featured locations in Cuba’s Oscar-nominated film "Fresa y Chocolate". Famous for its impeccable service and tasty meals, La Guarida has welcomed everyone from Beyoncé and Jay Z, to Robert de Niro, Jon Bon Jovi, and the late Karl Lagerfeld.

Feeling like a celeb already? You can do Cuba too! Start planning your tailor-made trip with our Cuban travel experts. For more information and advice, feel free to call our team or through our Contact Us form. With more holiday experts of Cuban origin than any other British tour operator, our specialists really do know Cuba inside out.