On a pitch black night, treading carefully along a road from our hotel on the outskirts of a small town in western Cuba, we finally saw the flashing torchlight. It was our pre-arranged rendezvous and the torchbearer was our guide to a private house where we would engage in an illegal transaction.

What kind of nefarious activity could a small group of British tourists be up to in Viñales – a UNESCO World Heritage site? Arranging the smuggling of Cubans to Miami? Plotting against the Revolution?

Er... not quite. We were just on our way to get a delicious evening meal at an unofficial restaurant in the town. But this was something that would, if the authorities found out about it, land the proprietors a hefty fine, and possibly jail time. In the end, everything went smoothly and we enjoyed a tapas meal of lobster, prawns, chicken, pork, and a very tasty black bean soup (along with beers and mojitos) for only 15 pesos (about £9) each.

In a country where doctors earn around £15 per month it is a sad, but inevitable, fact that many Cubans are forced to engage in black market activity just to make a living. And although Havana has plenty of officially-sanctioned private restaurants (known as "paladares") offering decent grub, in many towns outside of the capital such establishments are few and far between, which means private homes have developed a neat sideline in cooking for tourists.

Viñales is a valley where many kinds of crops, particularly tobacco, are grown using agricultural methods that have not changed for hundreds of years. My girlfriend and I were there in order to see the spectacular views of the rocky outcrops that won the valley its World Heritage status. We also explored the Caverna Santo Tomás (Cuba's longest cave system), toured the valley on horseback and visited a tobacco farm – where we saw how tobacco leaves are grown, harvested and dried out before they are shipped to Cuba's famous cigar factories.

How we travelled from Havana to Viñales and back was something of a bonus. Our tour guide had managed to arrange transport in three 1950s-era taxis – two Chevrolets and a Pontiac.

"But this was something that would, if the authorities found out about it, land the proprietors a hefty fine, and possibly jail time."

Before Viñales, our tour had taken us (by minibus) to the town of Trinidad on Cuba's south coast. Trinidad, another World Heritage site that was founded in 1514, is very much geared towards tourists. It boasts several restored old buildings, has plenty of museums, a few decent paladares and bars, and is not far from the Playa Ancon – a sandy beach where you can enjoy the sun, swim and snorkel.

In this town we took part in another underground activity, although this time it was perfectly legal. And it was well worth experiencing the Discoteca Ayala – a nightclub that has been installed within a network of caves set in one of the hills that oversee Trinidad. After paying a fee of around £2, we descended several steps into a hollowed-out passageway that eventually led us to a huge chamber where tourists and Cubans alike were dancing to Modern Salsa and Reggaeton beats. Unlike any discotheque I had ever visited, this was a true 'Cavern Club' where everyone else seemed to dance well, although any concern about my own lack of dancing prowess was soon overcome with a few well-mixed mojitos.

Having finished our organised tour, we spent a week in Havana itself, where we made sure we ate at La Guarida. Long regarded as Havana's best paladar, it has been visited by the Queen of Spain and featured in the internationally-acclaimed 1994 Cuban movie 'Strawberry and Chocolate'. Here, a gourmet three-course meal for two, complete with a bottle of Argentine wine, aperitifs and coffee, will leave you with plenty of change from a hundred pounds (try that at a top West End restaurant!).

In the day, Havana occupies your time with its many museums, its Havana Vieja old town district and a wonderful seafront walk along the Malecón seawall (although walking along this wall when the sea is rough can lead to a drenching!). In particular, art lovers will adore the Museo Nacional de Bellas Artes, which houses a wide collection of art from the 16 th Century to the present day, and the Museo de la Revolución, a must for history buffs and a chance to see the Granma: the yacht used to transport Fidel Castro and Ernesto 'Che' Guevara from Mexico to Cuba in 1956 so they could begin the Cuban Revolution.

By night, Havana offers much more. We took in the Ballet Nacional de Cuba at the city's Gran Teatro – the Western Hemisphere's oldest operating theatre. And, since we were in town for New Year's Eve we decided to celebrate at a nightclub where Cuba's biggest Modern Salsa act, Los Van Van, was performing.

"Any concern about my own lack of dancing prowess was soon overcome with a few well-mixed mojitos."

Of course, no visit to Havana is complete without a trip to the Tropicana Nightclub, which was founded in 1939. Hundreds of dancers perform during the Tropicana's famous 'Paradise Under the Stars' cabaret show, although the night we chose to go we saw more rain than stars. A bottle of rum kept us warm enough, though!

Cuba is an unusual, often contradictory, country and a fortnight there is certainly not enough to fully appreciate the place. We plan to return.

Jon flew to Havana with Virgin

Tips:

- Take plenty of pounds or euros to change into 'convertible pesos'. Only a few hotels will take credit cards, and a hefty commission always accompanies credit card payments.

- Do not take dollars. Dollars can be converted but, due to the ongoing squabbles between the US and Cuba, this will be at a very unattractive rate of exchange.

- Get your jabs done: Hep A, Typhoid and Tetanus.

- Travel around the island is difficult and the little public transport that does exist is unreliable. A good way around this problem is to take a tour organised with a reputable business before you arrive in Cuba.

- If going outside of Havana, take plenty of insect repellent.

- Cubans see politics as a risky topic to talk about, so avoiding the subject with locals will save you, and them, much embarrassment.

By Jon Mainwaring