Havana is an enchanting and captivating city, with the twists and turns of its compelling history and rich culture laid bare in the surprising diversity of its architecture and kaleidoscope of citizens. Nowhere is there uniformity, with the hotchpotch of buildings and people presenting a different set of stop-and-stare images on every street. Policemen on military service lean against Soviet-era Brutalist office blocks; adherents of Santería, dressed all in white, stroll past Neo-Gothic churches; queues of smart, elderly socialites form outside Art Deco theatres; and taxi drivers in baseball caps tout rides in their fifty-year-old Buicks and Chevrolets in front of Neoclassical shop fronts. In the centre especially, almost every street seems to have an intriguing story to tell, whether one of colonial grandeur, bygone glamour, economic hardship or revolutionary change – and sometimes all of these, wrapped up in just one block.

The past and the present are closely interwoven all over this sprawling metropolis, with tenement buildings moulded from the mansions of imperial counts, 1950s department store signs hanging over entrances to community centres and government agencies occupying eighteenth-century convents. An infectious vitality pervades every neighbourhood, as life in Havana unfolds unselfconsciously and in plain view: front doors are left open, washing is hung out on balconies, domino players sit at tables on the kerb, conversations are shouted between buildings and families watch TV in exposed street-side living rooms. Even in the most touristy parts of the city, which double up as residential neighbourhoods, the locals make their presence felt.

Havana’s diverse districts mark distinct eras in the capital’s evolution. What was once contained within seventeenth-century city walls now forms the most captivating section of harbourside Habana Vieja, the old city, and the capital’s tourist centre. Soldered on to Habana Vieja is gritty, lively Centro Habana, often bypassed by visitors on their way to more tourist-friendly parts of town but home to the most striking and idiosyncratic section of Havana’s oceanfront promenade, the Malecón. Sharing the Malecón with Centro Habana is Vedado, heart of the city borough of Plaza, its attractive, leafy, open plan neighbourhoods blessed with most of the city’s abundant theatres, cabarets, nightclubs and cinemas. From here you could walk the couple of kilometres to the vast and famous Plaza de la Revolución, with giant monuments to two icons of the Cuban struggle for independence, Che Guevara and José Martí. Beyond Vedado to the west, on the other side of the Río Almendares, Miramar ushers in another change in the urban landscape. Modelled on mid-twentieth-century Miami, this part of the city comes into its own at night, with some of Havana’s most sophisticated restaurants and best music venues scattered around the leafy streets.

Brief history

Havana’s success and riches were founded on the strength and position of its harbour – the largest natural port in the Caribbean. However, the original San Cristóbal de la Habana settlement, established on July 25, 1515, St Christopher’s Day, was actually founded at modern-day Batabanó, on the south coast of what is now Mayabeque province. It wasn’t until November 25, 1519, that the city was relocated to the banks of the large bay known as the Bahía de la Habana.

Port, bridge and gateway

The early settlement began to ripple out into what is now Habana Vieja, with the first streets established down on the waterfront between the present-day Plaza de Armas and Plaza de San Francisco. However, it was with the discovery of a deep, navigable channel through the treacherous shallow waters between Cuba and the Bahamas that Havana really took off as a major city, becoming a bridge between Spain and the New World thanks to its strategic location on the newly established trade routes.

As the Spanish conquistadors plundered the treasures of the Americas, Havana became the meeting point for the Spanish fleet on its way back across the Atlantic. For several months of the year, ships returning from all over the Americas laden with precious cargoes would slowly gather at the port until a force strong enough to deter possible pirate attacks in the Caribbean had been assembled. An infrastructure of brothels, inns and gambling houses sprang up to cater for the seamen, and the port itself became a target for frequent attacks by buccaneers.

Fortification and free trade

In 1558, after consolidating shipping operations by making Havana the only Cuban port authorized to engage in commerce, Spain started a long period of fortification with the construction of the first stone fort in the Americas, the impressive Castillo de la Real Fuerza. Work started on the Castillo de San Salvador de la Punta and the formidable Castillo de Los Tres Reyes del Morro in 1589 and was finally completed in 1630. Three years later a protective wall began to be built around the city, and was completed in 1740.

Assaults on the city persisted, however, and in 1762 Havana fell to the British. The free trade that the port enjoyed during its brief eleven months of occupation – the British swapped Havana for Florida – kick-started the island’s sugar trade; previously restricted to supplying Spain, it was now open to the rest of the world. Spain wisely kept British trade policies intact and the consequential influx of wealthy Spanish sugar families propelled Havana into a new age of affluence.

The building booms

The nineteenth century was a period of growth, when some of the most beautiful buildings around Habana Vieja were constructed and the city enjoyed a new-found elegance. At the same time, crime and political corruption were reaching new heights, causing many of the new bourgeoisie to abandon the old city to the poor and to start colonizing what is now Vedado. By the 1860s the framework of the new suburbs stretching west and south was in place.

In 1902, after the Wars of Independence, North American influence and money flowed into the city, and the first half of the twentieth century saw tower blocks, hotels and glorious Art Deco palaces like the Edificio Bacardí built as the tourist industry boomed. Gambling flourished, run by American gangsters like Meyer Lansky, who aimed to turn Havana into a Caribbean Las Vegas.

Equality, decay and rebirth

The Revolution put an abrupt end to all this decadence, and throughout the 1960s the new regime cleaned the streets of crime and prostitution, laying the basis for a socialist capital. Fine houses, abandoned by owners fleeing to the US, were left in the hands of servants, and previously exclusive neighbourhoods changed face overnight. With the emphasis on improving conditions in the countryside, city development was haphazard and the post-Revolution years saw many fine buildings crumble while residential overcrowding increased, prompting Fidel Castro to take action. Happily, since the 1990s there have been steady improvements, with redevelopment work recapturing some of the former glory, especially in the worst-affected areas of Habana Vieja.

Today there is a growing prosperity in Havana, evident from fancy restaurants full of locals, increasingly well-appointed houses, and new cars on the roads. Although many of its citizens still live in poverty on a minimum of resources, new housing developments springing up on the city’s outskirts and improvements in travel infrastructure speak of important social investment and the efforts made to address the city’s increasing inequalities.

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