Caption: Actress and model Margaux Hemingway at her grandfather, Ernest Hemingway's, house, February 1978 in Havana, Cuba. The house, known as Finca Vigía, has since been turned into a museum.

“A mind that is stretched by a new experience can never go back to its old dimensions.” So says Oliver Wendell Holmes Jr., one of the most talked about justices who sat in the US Supreme Court.

Exploring the unknown broadens your perspective and opens your eyes to a different side of the world. It is this reason that travellers are advised to seek out lesser-known places – of which, one of them is Havana.    

Popularised in pop culture by films like The Godfather II, Dirty Dancing: Havana Nights and The Fate Of The Furious, the city also makes a prominent appearance in music, most recently in a song by Camila Cabello.

Aptly named Havana, the hit single by the American singer-songwriter went on to become the biggest song of 2018, played 888 million times on Spotify and streamed 2.6 billion times worldwide.  

In October 2019, Havana joined UNESCO’s Creative Cities Network due to its legendary creativity in music. What makes Cuban music so unique is its combination of genres from the likes of folk, son and rumba, which has in turn, contributed to the development of jazz and salsa.

Explore Havana The Hemingway Way

Famed novelist Ernest Hemingway wrote his world-renowned novel, The Old Man And The Sea, in Cuba. Having fallen in love with the country, Hemingway eventually became a permanent figure in Havana.

He often stayed at a farmhouse called Finca Vigia, located east of the city. Even today, many of the places frequented by Hemingway (affectionately known as “Papa” by the locals) remain open as a tribute to the Pulitzer and Nobel Prize recipient.

From daiquiris at El Floridita to mojitos at La Bodeguita, Papa Hemingway’s legacy in Havana carries on. Visit Room 511 on the 5th floor of Hotel Ambos Mundos in Old Havana, which he frequently stayed in before moving into Finca Vigia, now a museum, preserved just the way it was when he left Havana after Cuba’s 1959 revolution.

Cabaret Tropicana was also one of Hemingway’s favourite evening entertainment spots – the open-air cabaret has been wowing crowds for over 80 years, drawing notable guests from the likes of Marlon Brando, Elizabeth Taylor, John F. Kennedy and more.

Shot on location, the 2016 film Papa Hemingway In Cuba (given a scathing 12% score by Rotten Tomatoes) showcases even more of Havana’s beauty. Our recommendation? Stay for the sights, but skip the script. 

Immerse Yourself In The Culture-Rich Vedado Quarter

Once notorious as a Mafia-run district, Vedado is now home to the city’s affluent residents. Built in the shape of a grid, Vedado means “forbidden” in Spanish, but has since evolved into an easily-navigable and enjoyable walking experience for visitors.

Along the way, take in the array of interesting buildings, boasting a mixture of neoclassical, art deco, colonial and more – some remain as residential homes, while a number have been converted into state offices or embassies.

But what might be of interest to music lovers are the ones that have since become key players in the nightlife and culinary scene, like La Escencia, Piano Bar Delirio Habanero, PaZillo and Los Naranjos. Drop by to feast your ears on live performances while you sip on Cuban cocktails and enjoy some local nibbles.

Make your trip to Vedado worthwhile by checking out Fabrica De Arte Cubano (which translates into Cuban Art Factory), dubbed as one of the world’s 100 greatest places by Time magazine.

This cooking oil factory-turned-community creative hub brings together a mishmash of art and culture, from galleries to performance art to concerts and beyond. With so many programmes lined up daily, you’ll be spoilt for choice.

Also in Vedado (set atop a hill) is the famed Hotel Nacional. It was once a tropical paradise, favoured by the who’s who in showbiz and society. Ernest Hemingway (more on him below), Rita Hayworth, Frank Sinatra, Ava Gardner, Winston Churchhill and Yuri Gagarin, to name a few, have spent time here. The hotel even served as Fidel Castro’s headquarters for aerial defense during the Cuban Missile Crisis in 1962.

Combine Leisure And Learning Into One Trip

Make the most out of your upcoming trip to Havana by signing up for a music-related course at one of the many schools available. One of the most reputable institutions is Havana Music School.

It offers anything from one-day percussion workshops to weekly intensive courses for learners of varying levels. If you’re looking to jam with other professionals, book a “Musical Ensembles” slot, which allows you to play your preferred instrument alongside three other Cuban musicians

If something more intimate is what you have in mind, try staying at a casa particular (private home, similar to an Airbnb even before it was known as such) belonging to a local musician, where you can trade stories and get a first-hand insight into their lives.

You’ll definitely find no shortage of places to stay in. Run by husband-and-wife professional musicians Alex and Lindiana, Casa De Musicos comes with glowing reviews from music and culture lovers from all around the world.

The duo performs in a band called Lindiana Y Mantra, with Lindiana as lead vocals and Alex playing the saxophone.

Dine In A Restaurant Owned By A Famed Music Video Director

What do 1990s artists like A-Teens, Dr Alban, Lumidee and The Rasmus have in common that could have the trail ending up in Havana? Well, all of them have had their music videos directed by Michel Miglis, a Swedish audiovisual producer, who also directed a feature-length film dedicated to the rose of reggaeton in Cuba, entitled El Medico: A Cubaton Story.

Touted as Cuba’s first Scandinavian restaurant, Casa Miglis is an amalgamation of Miglis’ Swedish-Greek heritage with his Cuban wife’s culture – as is evident from its menu. At Casa Miglis, you can simultaneously feast on Grandma’s Swedish Meatballs, Souvlaki (Greek-style barbecued pork), Cuban Seafood casserole and Scandinavian shrimp toast.

The bar decor is as eccentric as the food – think wooden-backed chairs suspended mid-air on a wall, holding anything from liquor bottles to patrons enjoying their late-night drinks. If you’re lucky, you might even spot a few local celebrities or even Miglis himself!

Enjoy The Colourful Celebrations Of Pride

When the sun goes down, the stars come out. And by “stars”, we mean quite literally. Havana’s thriving drag scene is a far cry from the first few decades after the Revolution, which deemed these events as illegal. Today, inclusiveness is big in Havana, as can be seen from the number of clubs, bars and spaces where all are welcome.

Don’t forget to check out Cabaret Las Vegas between Central Havana and Vedado, where the city’s top drag queens or “transformistas”, Imperio and Margot, have regular weekly performances.

Cafe Cantante Mi Habana also hosts Proyecto Divino, which offers an extensive drag show, complete with dancers. What makes this unique is that the event, held on Saturdays, has the full support of the Cuban National Center For Sex Education, and is officially recognised by the Cuban authorities as a LGBTQ+ friendly space.

Lose Yourself In The Music And Movement

The weeklong Havana Jazz Festival (which took place in January) saw jazz fans coming together to enjoy live music from the industry’s top performers. But if you missed it, don't fret. There are still plenty of music-related events to enjoy in the city.

Experience an evening at La Zorra Y El Cuervo, a top jazz bar in Havana, accessible via a red telephone booth on ground level. If your passion lies in dancing, you might also want to spend the wee hours of the morning at a salsa club like Casa De La Musica.

If not, try your hand at a salsa or rumba class and pick up some basic hip-swaying moves. You can even make way to Callejon De Hamel on a Sunday, where the brightly-coloured alleyways by Cuban artist Salvador Gonzales Escalona become the backdrop for neighbourhood rumba parties.

Cover Image: David Hume Kennerly via Getty Images

Writer | Michelle Tan

Underneath her RBF, Michelle is actually a friendly raccoon. Loves collecting ugly things, changing her hair colour, and dinosaurs (not necessarily in that order).