City slicker in Havana

Why visit?

Havana, the most captivating city in the Caribbean, has any number of treats to offer visitors. Exquisitely dilapidated streets; mighty forts; iconic hotels, from the colonial to the uncompromisingly modernist; a pulsating street life; fleets of classic cars – in various states of disrepair; dough-soft beaches lapped by turquoise waters; the world's tastiest rum and finest cigars; virtuoso musicians jamming on every corner and in every unassuming bar; a vibrant art scene; and warm, good-humoured, highly educated locals who know how to laugh and live in the moment despite the pressures of everyday life in this land of shortages and hardship.

To know this city, even just to pass through it, is to love it, and now, more than any other moment, is the time to visit.

Having just celebrated 50 years of Revolution, Cuba is like the ship that is sailing off into the sunset – except that its Fidel-shaped anchor is still dragging in the sand. With succession of power having passed to Raul Castro, the communist status quo is intact for now (despite pragmatic Raul's subtle loosening of the reins, and the prospect of President Obama lifting the travel ban on American tourists to Cuba). But once Raul goes, it's anyone's guess as to what will happen on the island.

Cuba is at a tipping point. Obama has already lifted restrictions on Cuban-Americans travelling to the country (who were promptly blamed by Fidel for introducing swine flu). Go now, before millions of Americans head for what to them is still a tantalisingly prohibited island, while you can still drive with the wind in your hair through blissfully empty highways, with no advertising in sight, just the occasional rousing revolutionary slogan.

Don't miss ...

... a walking tour of Old Havana. The Unesco-protected slice of the city, which is banked by the waters of the port, is being restored to its former glory.

... La Plaza de la Revolucion. Its vast concrete wastelands are flanked by faceless government buildings, but it's notable for the Jose Marti memorial (Cuba's hero of independence) and a bronze statue of Che Guevara.

... El Morro, the pirate-proof fortress that dominates the north-eastern side of the harbour and has great views over the crumbling tower blocks of the Malecon.

... Real Fabrica de Tabacos Partagas. The best-run museum in Havana is the working tobacco factory behind the Capitolio Building, which offers English-speaking tours (open 9am-11am, 12.30pm-2.30pm, Monday to Friday; buy tickets from the Saratoga, Parque Central or Telegrafo Hotels).

... a visit to the Piano Bar del Hotel Florida, at Calle Obispo, where local salseros strut their stuff on the tiny dance floor to a live band every night of the week.

What's new

Central Havana:

Wedged between semi-salubrious Vedado and Old Havana, Centro Habana, with its dilapidated streets and not a blade of grass in sight, is often bypassed by newcomers but offers an insight into the daily lives of Habaneros. Galiano, Neptuno, Dragones and San Lazaro are streets which are good for watching kids playing on scooters fashioned from bits of wood; women in curlers chewing the fat, and bicycle taxi-boys commenting on every woman who passes by. El Malecon, the famous seaside walk, is lined with decaying buildings that are now slowly being refurbished. This is a focal point; at dusk it is thick with lovers taking the salty air. Watch rumba dancers on Sundays, between noon and 3pm, at Callejon de Hammel entre Hospital y Aramburu, a luridly painted alleyway that's become a shrine to African-Cuban culture. You can also party at Cuba's cult music hall. La Casa de La Musica, at Galiano entre Neptuno y Concordia, is where legendary bands such as los Van Van and Bamboleo play weekly.

Don Cangrejo:

This long-standing seafood restaurant in swanky (in Cuban terms) Miramar is enjoying a renaissance because its kidney-shaped pool and gardens, splashed by the ocean, have become the place for the new generation of monied, bohemian young Cubans to sway to nueva trova on Friday and Saturday nights. Expect bands such as Ocha y su grupo or David Torrens – book ahead to guarantee a table.

Details: Ave 1, between 16 & 18, Miramar (00 53 7 204 4169).

Latin American Film Festival:

This new festival, based in the Hotel Nacional, runs from 3 to 13 December and will showcase both Latin and non-Latin films. There's a host of related parties and events, some held in the romantic gardens of this iconic gambling hotel, once controlled by the mafia.

Details: habanafilmfestival.com

Peña del Grupo Moncada, Jardines de 1830:

Set in gardens facing the sea, this stunning club has been resurrected as one of the hottest salsa spots in town for Sunday night dancing between 6pm and 11pm. There's a vibrant local crowd with just the right amount of tourists and normally a fair amount of group bumping and grinding led by Grupo Moncada and its dancing band of brothers. Like enforced aerobics, but more fun. Details: Malecon, esquina 20 (00 53 7 838 3091)

El Sauce

For a low-key place to listen to live music and chat to friends (a rarity in this noise-addicted town). El Sauce (pronounced Souw-say) is the new kid on the block for Havana hipsters. The al-fresco venue is based in an old mansion in the Playa district and has a changing roster of up-and-coming artistes such as Raul Paz. Drink a slow daquiri under the stars, enjoying lazy table service; don't bother to show up until 9pm, when it gets going.

Details: Corner of Calle 90 & Calle 30, Playa (00 53 7 204 7114)

Hotel Saratoga:

Still the only decent boutique hotel in Cuba, it remains recommendable for the quality of the food in its street-level restaurant, mezzanine bar and rooftop bar and restaurant; standard of service; access to decent cultural tours through its in-house travel agency, San Cristobal; rooftop pool with awesome views; spacious bedrooms with quality bathrooms; and jolly, efficient staff.

Details: Prado 603, Esquina Dragones (00 53 7 866 4317; hotel- saratoga.com).

Insider's secret

Alexy Soto Canizares, artist and teacher:

"Ten CUC [the Cuban pesos which are convertible for tourists] in a taxi from town should get you to the white-sand beaches of the Playas del Este. By far the most fun of these is Santa Maria del Mar – just ask the taxi driver to drop you off outside the hotel Tropicoco. Here you can eat lobster from a beach shack, drink mojitos till the sun goes down, listen to live music, have a massage, swim in transparent waters, walk along the beach and, who knows, maybe pick up a new Cuban love interest. I call it 'the beach of the mix' because it's so amusing to watch Cubans and locals interacting."

How to get there

Four nights in Havana costs from £739 per person, based on two sharing, with Virgin Holidays + Hip Hotels (0844 573 2460; vhiphotels.co.uk). The package includes return flights with Virgin Atlantic from London Gatwick, private transfers, and accommodation at Hotel Saratoga.

Further information: Cuban Tourist Board (020-7240 6655; travel2cuba.co.uk).