Our Dan in Havana

Apparently we’ve all got to rush to Cuba before Fidel Castro snuffs it, the US embargo is lifted and the Americans turn the place into a theme park. ‘But you might not like it,’ warns my friend Simon, who used to live in Havana. ‘If you’re after luxury boutique hotels and world-class food, you’ll be disappointed.’ As it transpires he is half right. True, the food and the accommodation aren’t exactly five-star, but in spite of this, Cuba turns out to be the trip of a lifetime.

Cuban tourism is booming right now and looks set to continue to do so after Fidel has gone. For the first time since the glorious revolution/Communist takeover* (*delete according to your political leanings), Cuba is flirting with capitalism. Raúl Castro, who took over from his ailing brother in 2006 and was voted in again as president earlier this year, has introduced a series of progressive new laws, including ones that allow Cubans to set up businesses such as paladares (small restaurants) and casa particulares (B&Bs) in their houses.

Staying and eating in these pop-up and pot-luck family-run places is the way to experience Cuba, rather than cutting yourself off in a characterless all-inclusive beach resort. We now know this, having kicked off our trip with two days at a thoroughly underwhelming all-inclusive at a beach called Cayo Santa Maria, a couple of hours’ drive from Havana, full of fat Canadians getting fatter. Maybe Simon was right. But once we arrived in the town of Trinidad, I thought: ‘OK, now I get it.’

Trinidad is a living museum of exquisitely preserved, sun-bleached, pastel colonial buildings built along narrow cobblestone streets lined with vintage cars and grizzled old dudes in hats impassively strumming battered guitars. The town ballooned on the spoils of sugar and is now the Pictionary definition of faded splendour. Photographers rave about the quality of the light at sundown. It’s like a film set.

The first casa particular we called at was full. No problem: the smiley owner ushered us around the corner to introduce us to her sister Dailyn and her husband Rolando. We had a comfortable, if basic, en suite in their family home for £16 a night. That first evening we feasted on lobster and bottles of Cristal — the local beer, not the bling champagne — before hitting the nearby bars for Cuban ron and son (rum and live music).

The following day we toddled down the cobbles to take our pick of the classic cars that earn their upkeep as taxis. An emerald green 1950s Buick took us the 15 minutes down the road to Playa Ancón, a palm-fringed, white-sand beach. We returned that evening almost as red as the lobster we ate for dinner again. (Well, it was so cheap!)

Next stop was Cienfuegos, the ‘Pearl of the South’, considered Cuba’s cleanest and most beautiful city. We’d called ahead and managed to get a modern split-level suite at a guesthouse called Bella Perla Marina for a bargain £30 a night. Call the legendary Waldo and tell him I sent you.

Having walked Cienfuegos’ grand and spacious boulevards, we headed to Hotel La Unión for lunch and a swim (£6.50 to lie poolside for non-residents). At sunset we had a mojito on the rooftop bar overlooking the bay, before taking a bicycle taxi down Paseo del Prado, Cuba’s longest street — lined with parading couples, men fishing for their supper and kids learning to box.

We had a couple of days in the capital before flying home and spent them ticking off the Havana bucket list: a mojito at La Bodeguita del Medio and a daiquiri at El Floridita — the writer Ernest Hemingway’s two favourite drinks in his two favourite bars; a night at Buena Vista Social Club; a waterside stroll at sunset along the Malecón. We even found a couple of spectacular restaurants — notably the tiny Paladar Doña Eutimia and La Guarida, Cuba’s finest diner.

At Hotel Santa Isabel, a splendid colonial mansion on one of the most impressive squares in the old town, we were offered an upgrade to a suite that had sun streaming in through stained-glass French windows overlooking the Plaza de Armas. Sold. As I sat on the balcony reading The Old Man and the Sea, mojito in hand, a street band came to serenade us from the square below in exchange for a couple of coins. Basking in the evening sun, drinking it all in, I remember saying to my wife: ‘I’m so perfectly happy right now, I wish I could bottle this feeling.’

We’ve since tried, via a souvenir bottle of premium Havana Club rum and Buena Vista Social Club on Spotify. Close but no Montecristo.

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Virgin Atlantic flies direct from Gatwick to Havana twice a week from £670 return (virgin-atlantic.com). Cuba isn’t the easiest place to organise travel and you’ll need to book transfers, good restaurants and hotels ahead. AudleyTravel.com took care of all Dan’s arrangements, though currently it does not book casas as it cannot guarantee the quality.