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“I’ve lived in Cuba on and off for over 20 years now...

I've watched the winds of change gather, blow and sometimes disappear – only to come back again. So when I'm (frequently) asked about my favourite things here: from where to stay, what to do – even who to hang out with – the answers always come thick and fast! 

In many ways, I still love all the touristy stuff: the cars, the music, and the beaches. But I also have a deep appreciation for the beautiful new experiences and places to stay that have popped up over the last decade, created from the blood, sweat and tears of ordinary Cubans who have an entrepreneurial mind-set and a resourcefulness to see their ideas through from start to finish.

As a visitor, I’d first get myself checked into a nice hotel in Havana.

​My current favourite is probably Gran Hotel Manzana Kempinski La Haban, carved out of a handsome neoclassical turn-of-the-century shopping arcade, opposite the Gran Teatro de Habana and sitting side-by- side with the gorgeous Cuban wing of the National Fine Arts Museum – which is unmissable, by the way. It has the biggest rooms with high, vaulted ceilings, the best breakfast, the best spa, and a panoramic rooftop pool. 

If I wanted privacy and a sense of place though, I'd gravitate towards Havana's boutique collection of mid-century villas, colonial homes, pretty penthouses and old town pied-à-terres.

Of the latter, my current crush is Casa Plaza Vieja: looking straight out onto the famous square, it has a lovely rooftop and stunning interiors by two French interior design doyennes who also happen to own it.

Alternatively, I’d check into Malecon 663 (another icon of French taste), created by local Habanera Sandra, who comes by way of Marseilles. Sandra does a lovely sunset experience with cocktails, DJs and jazz musicians on her chic rooftop; and also supports local Cuban artisans by selling their hand-made jewellery and soaps.​

I’m drawn to hoteliers outside of Havana who support other local businesses as well – like atmospheric guesthouse Mogotearte in Viñales, run by Luis, a local politician (who recently had fragments of a meteorite land on his front patio!); and Santa Clara's Suite Florencia, a Cuban/Italian-run private vintage-styled guesthouse which also sells local pieces.​

For a first-time visit, you can’t go wrong starting your stay with a great day out in one of Havana’s ubiquitous classic cars.

There are roughly 60,000 on Cuba's roads, accounting for about a tenth of the nation’s cars. For a population of 11 million, it’s a low car-to-person ratio (and if it weren’t for the crater-sized potholes, pricey car rentals, lack of road signs and sleeping dogs, driving in Cuba would be a dream). So these treasured collectible cars – a metaphor for the Cuban national character – have a whole lot of stage presence and neatly tell tales of the island’s recent history.

Shortly after coming to power in 1959, Fidel Castro’s government stopped imports on both foreign cars and their parts. Then the USA signed a commercial embargo blocking the sale of all American-made goods to Cuba. The bloqueo, as the Cubans call it, prevented all exports aside from food and medical supplies, so the flow of American-built cars, bikes, and trucks was well and truly stemmed. So from that moment on, the car scene here was cryogenically frozen, and over the ensuing decades, cars already here were passed like family jewels down through the generations.​

To this day, they glide around the island like props in a 1950s feature film.

They're one of the island's most pronounced visual reminders of the 'time warp' that it's inhabited since the Revolution (it's somewhat ironic that these iconic Cuban classics are, of course, mainly American).

Dodges, Studebakers, Chevys, Hudsons, Buicks, Fords, Oldsmobiles, Pontiacs, DeSotos and Chryslers are a standard sight; while American trucks dating back to 1929 still chug along the dusty country roads.​

​Next, if you have any whiff of literary interest, I'd dive head-first into Ernest Hemingway's story.

In Havana it's easy to follow in his footsteps on a historical tour of 'his' Cuba. Visit Finca Vigía, his old farm – preserved as if in aspic – on the outskirts of town; explore Cojímar where a monument was erected in his memory; visit the Floridita Bar where he downed many daiquiris, and more.

Of course, the best way to do it is with those who have some serious insider knowledge, like my guide Nelson, who only does Hemingway tours; and Valerie Hemingway, Papa's old assistant and the former wife of one of his sons, whom she actually met at the writer's funeral.

​The key to Havana is also music and dance.

Plug into the social scene by catching a band at Vedado’s Fabrica de Arte (FAC), a multi-arts space carved out of an old factory, and currently the city’s hottest nightspot.

Hear top jazz musicians late at night in basement bar El Zorro y El Cuervo; solo violinists in the exquisite Iglesia de San Francisco de Paula, famous for its classic Sunday recitals; or see live salsa at iconic Casa de la Musica, which has a downtown outpost in Centro Habana and a suburban outpost in the Playa municipality. It’s full of hustlers, but it’s frenetic, energetic, and fun.​

​Food-wise, Cuba's rich cuisine has evolved out of the island’s emigrant history, melding Spanish, African, Chinese, Arab and indigenous influences, amongst others.

Yet many visitors to Cuba complain of having eaten badly. There are various reasons for this – terrible food shortages and patchy supply to restaurants being one – but it is possible to eat extremely well here.

Get a handle on the whys and wherefores of the complicated food scene, and sign up to a food tour; my favourite right now being the one led by Raulito, charismatic owner of the lovely Havana paladar (private restaurant) Grados. He'll take you to talk to restaurateurs, to small organic farms and small-holdings, and to visit the famous organoponicos – organic city farms to discover how sustainability works within the Cuban context. Then, follow in the footsteps of Prince Charles and Camilla during their recent visit, and have a cocktail-making class with Diana, the owner of Jíbaro AlaMesa, one of my favourite private restaurants in Old Havana.​

​I'm a sucker for nature too, and go mad for bird-watching in Sierra del Rosario, a mountain range in western Cuba's Pinar del Río and Artemisa provinces.

Also in this area I love Viñales village in the spectacularly beautiful, UNESCO-protected valley of the same name. Here, my favourite thing is horse-riding (I grew up on a farm in County Cork, Ireland, so I still fancy myself as a bit of a horse-whisperer!). The horses may be smaller and a little more standoffish, but they are much loved and valued in Cuban culture (and the only transportation in many rural settings). 

My other favourite activity? Climbing mogotes – limestone peaks that fill the valley (it's not for the faint-hearted). Trinidad meanwhile is eternally popular, and undeniably atmospheric; and swimming beneath waterfalls in the nearby Escambray Mountain Range sublime.

There are many other amazing places too. I love Baracoa for its utter beauty, and amazingly quiet way of life; Santiago de Cuba, Cuba's second city, particularly for its vibrant, magnetic August carnival – hot and sweaty, but worth it; and Pinares de Mayari, for the utter lack of tourists and unexpected, almost Alpine scenery. Other curious provincial outposts have also attracted my attention lately – like Sagua La Grande, a once-rich sugar town with fascinating architecture and appealing atmosphere; and nearby Isabela de Sagua, a wind-blown coastal fishing village with eccentric seafood cafés set on overwater stilts.​

​They do say it's in the strangest of places that you'll come across the most interesting people...

...and Cuba often delivers: intelligent, educated locals devoted to their home, with perfect English and full of incredible anecdotes. They often make the best guides, so I'm always on the lookout. And it's this incredible, never-ending resource of human intelligence and charm that, above anything else really, keeps me calling this place home.

Featured Hotels

  • Gran Hotel Manzana Kempinski La Haban Havana

    One of the most beloved buildings in the historic heart of UNESCO-crowned Old Havana, and on the best street in the entire city, Kempinski have taken the storied Manzana de Gómez building – once Cuba’s first European-style shopping arcade – and turned it into an absolute showstopper of a hotel.

    Call us on 01244 567 000 to start planning your next holiday.

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