The coolest Caribbean island is back – here are the best winter holidays to have there

A few weeks ago I arrived in Havana by sea, having crossed the Florida Straits from Key Largo in a friend’s boat. A port authority officer, perched high at the top of the city’s famous Fosca building, came on the radio, asking who we were and where we were from. When told, he welcomed us with a cheerful: “Bienvenidos a Cuba!”

The island is my home which, given it’s one of the last bastions of communism and is daggers drawn with its neighbouring United States, doesn’t come without its challenges. Yet as the dying sun caused Havana’s great buildings to glisten – the Morro castle, the  Capitolio, the Hotel Nacional – I felt the old surge of excitement that always rolls over me on the road in from the airport.

I was back in a place where people find a way to live against the odds, and where they enjoy the company of outsiders. A warm place, in every way, where a penned-in human spirit expresses itself in art and music. All in a country raw in landscape and roiled by history. 

“Just look at it,” my partner Camila will say when we have fallen under the shadow of a wonderful bit of architecture. “And it’s in the Caribbean!”

The past two years have been rough all along Cuba’s 780-mile length. For the first year of the pandemic, the government kept the virus out effectively, but the loss of tourism was devastating for an already moribund economy. Then, as queues formed for food and medicine, the government opened the airports.

The virus spiked, overwhelming the fabled healthcare system. Cuba’s scientists had, notably, created homegrown vaccines; that at least gave Cubans a moment of pride. More than 80 per cent of the population has now had at least one dose of either Soberana-2 (sovereign) or Abdala (the title of a patriotic poem).





Ruaridh Nicoll at home in Cuba

I spent the lockdowns yearning to travel the country’s long crocodile length. One of my favourite things to do is to rent a car and take random backroads. With one turning you can find yourself in the 1870s, pulling over for a farmer driving a speedy carretón (a horse and trap) or ponderous oxen, often named “Comandante” and “General”. (It’s always worth remembering they would prefer a tractor.)

It was unsettling, early in the pandemic, when the music died in Havana. The government turned off the lights at my favourite trova house, La Casa de la Bombilla Verde, and smothered the drums at Diablo Tun Tun. Havana seemed to retreat as an idea. But now it is back. Venues are reopening, and once again salsa, son, trova and, of course, reggaeton can be heard on the street corners.

Still, shortages continue. Visitors can help. If you have spare antibiotics, bring them. Vitamin tablets, too. Pack coffee and chocolate, both of which will be received with gratitude and offers of assistance. And bring euros, in cash. Inflation has taken hold of the peso.

It’s more than five years since Barack Obama offered hope of a detente in the long cold war between the US and Cuba. During that year, Cubans invested, repairing exquisite houses for rent, opening new bars and restaurants. The difficulties of getting materials here – plus the pandemic – has meant those places are only just coming of age now. They, like the whole country, are worth visiting. The antipathy between Cuba and the US may have resumed but as my boat trip showed, the welcome remains strong. 

With quarantine for new arrivals ending today, and a full reopening of international travel from November 15, it’s time to focus on the people and the good times in this most beautiful of islands.

10 things to do in Cuba this winter

1. Fiery festival 

Las Parrandas de Remedios, a festival in the small central Cuban town of the same name, dates back to the 18th century but has been growing ever more popular with visitors. Starting around December 16, it culminates on Christmas Eve in a terrifying firework competition between two barrios. Unique, it’s gratifyingly close to the beautiful beaches of Cayo Santa María (book through cubagrouptour.com). Shift to Havana for New Year and be surrounded by music and dance. I would suggest renting a beautiful house like Villa Flora (villaflora.com) so you have a sanctuary from the bedlam. Alternatively, cubaprivatetravel.com is excellent for alternative accommodation.





You won’t be short on things to see and do during Las Parrandas de Remedios


Credit: Alamy

2. Dive deep 

Lorena Gonzalez Casuso is a champion free-diver who is happy to teach visitors the basics of a sport that takes you where, she says, you are “surrounded by the blue”. The waters off Havana are magnificent and full of fish, although travel with her to María la Gorda or Playa Larga and it gets even better. Lorena is also a superb spear-fisher, if that’s your thing. Contact her through her Instagram (@loreoceancuba).  

3. Country roads

It’s a great time for a road trip.  You will be welcomed with gratitude and alacrity as the first foreigners seen in two years. Journey Latin America (JLA) offers Trailblazer Cuba, a 10-day self-drive holiday, for £2,290 per person including international flights, excursions and pre-booked places to stay. If you prefer not to drive, JLA also offers a variety of guided tours (020 8747 8315; journeylatinamerica.co.uk). 

4. Happy hour

There are great new bars in Havana. Yarini (yarinihabana.com), named after a pimp who ran the old town barrio of San Isidro in the early 1900s, lit up inter-lockdown Havana. There is also Loft (Calle Oficios 402 e/ Luz y Acosta) which serves great Cuban cocktails, including the far too obscure Canchánchara in its traditional clay pot. But the place I’m most excited about, which will open in January, is Bleco. Set on Havana’s famed corniche, the Malecón, it is owned by one of Cuba’s most fabulous dancers, Lía Rodríguez (@liainside on Instagram) and has the city’s best barman, Wilson Hernández, making the drinks. It will be the place to party this winter.

5. Cuba by air 

While the roads in Cuba are better than you might imagine, the distances and potholes can be huge. Cuba Private Travel offers to lift you above all that. They will fly you to the island on an 18-seater twin prop from Cancún and then stop over in Havana, Cienfuegos, Baracoa, and Santiago, relaxing at the beach in Cayo Coco. This trip has the additional advantage of CPT’s brilliant owner Johnny Considine, who is my go-to for definitive advice on all the best places to stay – and should be yours, too. 





A sea of blue: enjoy the warm waters and powdery white sand of Cayo Coco


Credit: Getty

6. Chasing silver 

The finest natural environment in all of Cuba – and there’s a lot of competition – is Jardines de la Reina, a paradise archipelago off the south coast. It is a pre-eminent diving destination but is also the place to fly-fish for tarpon, bonefish and permit. You stay on a live-aboard boat for a week, hosted by Avalon (cubanfishingcenters.com). Having been left alone for two years, it will be particularly spectacular this winter. 

7. New casas on the rise 

Some of Havana’s most beautiful houses are being restored and turned into guest houses and home stays. The newest, and among the most beautiful, are JM7 and JM5 (jesusmaria7.com) with rooms looking out over Havana Bay. This is where Spanish treasure galleons once gathered before crossing the Atlantic. For elegance and to mainline into Havana’s rich theatrical life try Economía 156 (economia156.com), owned by Jazz Martinez-Gamboa, an actor and director, and his partner Stephen Bayly, former director of Britain’s National Film and Television School. Or take over all of Gardens’ four rooms (gardenshavana.com). Restored by Yunior Riveron, it is a real gem right in the middle of Old Havana’s liveliest barrio. For more suggestions of where to stay, see our guide to Havana’s best hotels





Experience an amazing home stay at Economía 156

8. All-inclusive or pay as you go  

Cuba has always been good for a getaway in an all-inclusive beach hotel. And right now, TUI is offering a seven-night stay at Varadero’s Royalton Hicacos from £840 per person in December, flying from Manchester. Personally, I prefer to pay as I go as the service is better. Royalton has just opened Mystique Casa Perla (mystiqueresorts.com), a rare boutique hotel on Varadero’s perfect white sand, which I haven’t yet visited. The best new spot is Kempinski’s resort on the gorgeous Playa Pilar in Cayo Guillermo (kempinski.com). I wrote about it last year just as it tried to open, but it was derailed by the pandemic. It will now open in January. 

9 A smoke with Big Toby 

There isn’t a more storied English expatriate in Havana than Toby Brocklehurst. Ask for a “Tobito” in one of the city’s many bars and you will be served a mojito in a pint glass. Meet him at the beach and you will be faced by a wobbly table set out with lobster and the finest grilled snapper, and by the big man himself pulling HP sauce and Gentleman’s Relish from a bag. But for the true Toby experience, accompany him on a tour of the tobacco fields of Vuelta Abajo, what he calls: “the Bordeaux of tobacco regions” (contact him at [email protected]).

10 Rum punch-up 

Rum, another great Cuban speciality, is having its moment. Havana Club (havana-club.com) is the most famous, but others are fighting for their place. We who live here invariably reach for Santiago de Cuba (ronsantiagodecuba.com), which has recently rebranded and added an eight-year-old to its portfolio. Its website offers recipe ideas. If spiced rum is your thing, well, God help you, but Black Tears (blacktears.com) is the new pirate on the block, its name taken from the beautiful song Lagrimas Negras. Most sophisticated though is Eminente (eminente.com), from luxury brand LVMH. They have even opened a Cuban hotel in Paris to celebrate their new drink, just in case you can’t make it all the way here (hoteleminente.com).


Perfect packages for Cuba

Its image may be fixed – a cocktail of sun, salsa and Spanish architecture – but Cuba is a country of surprising size, breadth and variety. In fact, it is the largest island in the Caribbean (the third largest, Jamaica, would fit into it 10 times over); a feat of geography that makes it a plausible playground for all manner of exciting escapes. Chris Leadbeater shares the best holidays to book now.

For the full picture

Few destinations are more romantic than Havana on a sweltering evening – music seeping from doorways, mojitos sipped in leafy courtyards. Cuba’s capital is an unmissable part of the experience – and yet, just one of many essentials. Last Frontiers (01296 653000; lastfrontiers.com) offers three nights in the city in its 15-day “Historical Cuba” tour – but the route also flits to southern rival Santiago, and the province of Granma that neighbours it. The tour calls on Trinidad (the country’s “third” city) too – which, as well as enjoying a glorious south-coast location, is a salsa hotspot. From £5,180 per person, flights included.





No trip to Havana is complete without sampling its famous rum


Credit: Getty

For a suntan

As with any Caribbean island, Cuba is a wonderful option for a getaway which involves a beach and nothing but a beach. The majority of its resorts are dotted along its north coast – most famously Varadero, which occupies a sliver of a peninsula, 100 miles east of Havana. If the range of accommodation isn’t huge – the template is an unpretentious four-star with a large pool in front – then that doesn’t diminish the scope for relaxation. A seven-night break to the (four-star) Blau Varadero hotel, flying in directly from Manchester on December 13, starts at £908 per person via Tui (020 3451 2688; tui.co.uk). 

For a sunset

The majority of holidays to Cuba tend to cram in a lot (see above) or very little (also see above), but a middle ground can be found. Tropical Sky (01342 395 461; tropicalsky.co.uk) ventures into it with its “Classic Western Cuba” package – a potted seven-night itinerary which begins in Havana, but rather than heading east and south, wanders west. This means Pinar del Rio, the rural province which makes up the left-hand tip of the island – gazing into the sunset in a blur of small fincas, splashing waterfalls, Santeria shrines and mist-shrouded mountains. From £1,759 per person, including flights.





The picturesque Pinar del Rio


Credit: Getty

For sport

While Cuba’s tropical climate dictates that it could never be described as “Alpine”, it has enough peaks and troughs to make it a challenge for cyclists (its tallest summit, Pico Turquino, tips its hat at 6,476ft). Exodus Travels (0203 993 4514; exodus.co.uk) runs a “Cycling Cuba” group holiday which explores the country over 15 days, tackling its loftiest mountain range (the southerly Sierra Maestra), and pedalling the north coast in Las Tunas province. Three editions are planned for 2022, from £3,599 per person, with flights.

For a family escape

Cuba’s affable weather and splendid scenery means it can also underpin a holiday with children. Journey Latin America (020 3131 7959; journeylatinamerica.co.uk) sells a 15-day “Family Cuba” trip that ticks off Havana, Trinidad and Pinar del Rio, and throws in salsa lessons and cycling excursions before it finally slumps onto the sand at Cayo Santa María. From £3,076 per person (flights extra).