Go now: Havana, Cuba

The city of Cadillacs, cocktails and the Castros has smartened itself up for its quincentennial celebrations, but hasn’t lost an iota of its raggedy charm. Hemingway would still feel right at home

As the city gears up to mark its 500th year, here’s why it’s time get lost in long Havana nights

Five hundred years of stories saturate the sultry streets of Havana, and yet, this one-time playground for hedonistic high-lifers remains full of surprises. You may still spot the odd vintage Cadillac on the streets, but change is stirring.

Last year’s presidential handover served up the latest twist to the national drama, signalling the end of the Castro brothers’ decadeslong hold over the position. And with significant restorations to landmarks complete for Havana’s quincentennial celebrations, it’s a fitting time to join the party.

A stroll down Paseo del Prado is a great way to introduce yourself to the Habaneros’ way of life. Hazy afternoons along this promenade often stumble into long nights, and hours can be lost prowling through the bustling weekend art market.

Wander off track into Old Havana to discover some of the city’s most impressive sights: the art deco Bacardi Building and the Gran Teatro de La Habana, where prima ballerinas often perform to stagestruck guests. You’ll also spot the white-domed El Capitolio, the renovated seat of Cuba’s national assembly and one-time scene of a diamond heist. A replica of the jewel (since recovered) is embedded inside the main hall floor.

Much of the city’s charm rests within its centuries-old colonial plazas. Admire Havana Cathedral, once described as “music turned to stone”, before pausing to sample the best mojito in town (according to Havanaphile Ernest Hemingway) at La Bodeguita del Medio bar.

Keep walking and you’ll find Plaza de Armas, the city’s oldest square, peppered with secondhand booksellers. Swing by the Museo de la Ciudad, too, for a history of Havana inside a former colonial governor’s palace. Then, take in the mish-mash of Cuban baroque and art nouveau façades at Plaza Vieja, before winding through the harbour-facing Plaza de San Francisco, where a fountain of lions proudly holds court. Then follow your ears and spend your evening – and night – somewhere where the salsa is live and the crowd is livelier, and maybe find a story twist of your own.