Travel Icon: Old Havana

Modern-day Cuba remains a clash of Spanish, American and communist cultures, and nowhere demonstrates that better than Habana Vieja

6 mins

I first plied the haunting streets of Habana Vieja in November 1997 during the post-Soviet economic meltdown that the Cubans euphemistically call the ‘Special Period’. Frozen in time, the city was like nowhere else I had ever visited.

Happy Havana 

Household washing fluttered from mildewed colonial buildings, craggy-faced men slapped down dominoes amid the omnipresent fug of cigar smoke, and snippets of soulful son music drifted out from cavernous houses to fill the streets and squares of the animated colonial core. If the Cubans were feeling despondent after three decades of shortages and rationing, they certainly weren’t showing it.

Ten years later and not much has changed, bar a shift in power between the Castro brothers and a greater number of inquisitive tourists wandering around in Che Guevara T-shirts. Cuba remains suspended in a dusty pre-revolutionary time warp, an intoxicating mélange of Jurassic American cars and infectious Caribbean rhythms that grab you by the heartstrings and lure you sensuously into their fold.

Coloured by 500 years of rollercoaster history, Habana Vieja lies at the centre of the modern day Cuban conundrum. It’s a small yet wonderfully seductive urban quarter that juxtaposes the gritty reality of daily city life with one of the best-preserved Unesco World Heritage sites in the Americas.

But beyond the resplendent architecture and small, quirky museums lies a neighbourhood of rare complexity that embraces life with a dynamic joie de vivre and is endowed with an ebullient Caribbean culture that can be peeled off serendipitously, layer by layer.

In context: a brief history

Inaugurated in 1514 as the most westerly of Cuba’s seven pioneer settlements, Havana was moved to its present site in 1519 when the saintly Friar Bartomolé de las Casas  conducted a solemn mass under a ceiba tree in present day Plaza de Armas.

Stealing the mantle of Cuban capital from Santiago in 1607 due to its strategic position on the lucrative Atlantic trade routes, the city quickly became a haven for sabre-brandishing pirates such as Jacques de Sores, who sacked the burgeoning settlement in 1555.

In response, the Spanish built an extensive network of forts such as ‘La Cabana’ (left) around the harbour, making Havana the best-protected city in the Caribbean. The Cuban capital grew rich on the sugar boom of the 1820s when wealthy landowners built their glittering abodes in the salubrious streets and squares of the Old Town -– but the prosperity didn’t last.

From 1850 onwards the city’s hub and money migrated west to the former forest reserve of Vedado, and Habana Vieja fell into a spiralling decline that continued unchecked for more than a century.

Help arrived in the 1970s when influential City Historian Eusebio Leal initiated an ambitious reconstruction campaign that by 1982 had attracted the interest of Unesco. For the past three decades Habana Vieja’s rich history, fossilised since the revolution, has been painstakingly pieced back together, brick by brick.


For 11 months in 1762-3, Havana was occupied by the British who wrested it from Spanish control after a 44-day siege. Spain regained the city at the Treaty of Paris in 1763 in exchange for the then Spanish colony of Florida.

How to do it: Amble around Old Havana

Covering an area of just 4.5 sq km, Habana Vieja’s compact urban grid is perfect for walking.

Start on the quarter’s main artery, Calle Obispo, a narrow, traffic-free thoroughfare that leads from Centro Habana to the leafy confines of  Plaza de Armas near the harbour.
At the street’s western end you’ll find El Floridita bar , a one-time Hemingway hangout where the author once – allegedly – sank 13 double daiquiris in one sitting. Attempting to emulate him today could prove costly given that the cocktails now sell for an astronomical CUC$6 (£3.15).

Ply Obispo in the daytime and you’ll encounter tourists, cigar hustlers, over-zealous waiters and earnest grandmothers clutching their ration books. Come back at dusk and you’ll hear seductive Cuban music emanating out of every other doorway.

Good places to drink and dance include the clammy La Dichosa , the riotous Lluvia de Oro and the congenial Café Paris . Follow the sounds and take your pick. In contrast to other Spanish colonial capitals, Havana grew up around four separate squares, each infused with its own unique flavour and function. Carry on down Calle Obispo and you’ll reach Plaza de Armas  ­– the oldest of the quartet – which hosts a book market, a city museum and the sturdy Castillo de la Real Fuerza , the oldest stone fort in the Americas, which today hosts an excellent ceramics museum.

Divert north along Calle Tacón to photogenic Plaza de la Catedral  and enjoy a light lunch al fresco at the famed Restaurante El Patio while admiring the impressive frontage of Havana cathedral, a building Cuban novelist Alejo Carpentier described
as ‘music turned to stone’.

Next, track back south along Calle Mercaderes past rows of old shops recently restored to their former splendour by Eusebio Leal, Havana’s renowned City Historian and the director of the restoration programme of the Old Town. Look out in particular for Marco Polo, a spice and herb store, and La Casa del Habano , a respected cigar outlet hidden inside the splendid Condes de Villanueva Hotel.

Turn left on Calle Amargua to breezy Plaza de San Francisco  for peek-a-boo glimpses of the harbour before heading a couple of blocks to the south-west for Plaza Vieja, Habana Vieja’s most architecturally eclectic square, with buildings ranging from the Mudéjar Museo de Naipes to the Gaudíesque Palacio Cueto.

Then, to get a feel for Havana’s gritty docks district – the birthplace of rumba – sink a beer in the sea-faring Dos Hermanos bar (Calle Sol) before dipping into the illuminating Museo de Ron for rum exhibits, spontaneous dancing lessons and a glass of Cuba’s potent national drink.

For an alternative view of Habana Vieja, drop south to Calle Luz and left on to Calle Compostela through a vibrant working-class community of more than 70,000 people who live in one of the most densely populated areas in the Americas. One of many social projects funded by tourist money, the Iglesia y Convento de Nuestra Senora de Belen  is a beguiling baroque church/convent dating from 1718 that is now a convalescent home for Habana Vieja’s senior residents.

Head south from here and turn right on to Leonor Pérez and you’ll end up at the Casa Natal de José Martí, a small museum dedicated to Cuba’s national hero. Now, back-track to your favourite-looking bar and get read for a party, Cuban style.

While you're there: Tackling the main draws

Plaza de la Catedral A triumph of Cuban baroque architecture crowned by the gorgeous Catedral de San Cristóbal de la Habana, this intimate plaza requires two visits; one during the daytime and one at night, when the winking orange lanterns and decorative 18th-century facades lend the square a distinctly ethereal quality.

Hotel Ambos Mundos (153 Obispo) If you’re intent on bagging just one Hemingway sight in Havana, try ordering your daiquiri in the downstairs bar of this classic pastel-pink hotel, where the rum-happy ‘Ernesto’ was a well-known barfly in the late 1930s. The airy lobby showcases an excellent pianist while, upstairs on the fifth floor, you can peer inside room 511 where Papa purportedly penned For Whom the Bell Tolls.

Museo de la Ciudad (Plaza de Armas; admission CUC$3/£1.60) A classic chronology of Havana history is displayed in this former colonial governor’s palace that dominates Plaza de Armas. Avoid the tip-hungry guides and saunter from room to room at your own pace.

Edificio Bacardi (Av de las Misiones) The Bacardi rum family, synonymous with Cuba until the early 1960s, commissioned the construction of this fine art deco building as an office block in the 1920s. Embellished with Capellania marble and multi-coloured bricks, the structure is considered to be one of the finest examples of the style in Latin America.

Fortaleza de San Carlos de la Cabaña (Morro-Cabaña Military Park; admission CUC$4/£2.10 day;CUC$6/£3.15 night) Situated on the other side of the harbour, but included in the Unesco listing, this formidable 18th-century fort is the largest of its kind in the Americas. There’s a theatrical ‘shooting the cannon’ ceremony nightly at 8.30pm.

5 alternative Havana highs

1. Iglesia y Monasterio de San Francisco de Asis (Plaza de San Francisco)

Most travellers gravitate towards this eye-catching baroque church to admire its zealous religious paintings, but come back after dark and you can enjoy refined classical music concerts in the church’s old nave two or three times a week.

2. Casa de la Obra Pía (158 Obrapía)

A richly decorated former aristocratic home, this residence today serves as a workshop and sales outlet for a local sewing and embroidery cooperative.

3. Secondhand book market (Plaza de Armas)

With a famously high literacy rate, the Cubans are voracious readers. Check out what’s on offer at this daily outdoor market.

4. Backstreet wandering

To unmask Habana Vieja’s true Cuban spirit, wander a block or two to the south of touristy Calle Obispo on Calles Obrapía or Lamparilla where museums and souvenir stalls are replaced by ration shops, asthmatic Buicks and young kids playing baseball in the street.

5. Taller Experimental de Gráfica (6 Callejón de Chorro)

Cutting-edge Cuban artwork is displayed (and sold) in this buzzing workshop, which confirms the country’s status as a pioneer in the field of Latin American painting
and printmaking.

Planning your trip

When to go

You can see most of the sights in Habana Vieja in three days, but if you want to get a good take on the whole city, bank on five days to a week. Cuba’s peak tourist season runs from early December to late March. The upside of travelling at this time is the weather, which is sunny (but not too hot) and free from the threat of hurricanes. The downside is that prices are higher and crowds heavier.

Getting there

Most travellers to Cuba arrive at José Martí International Airport, a 40-minute, CUC$20 (£10.60) taxi ride from Habana Vieja. From the UK there are direct flights with Virgin
and Cubana airlines. Alternatively, fly with Iberia via Madrid or Air France via Paris.

All travellers to Cuba are required to purchase and fill out a tourist card, which must be handed in at immigration on landing. Cards are normally provided by the travel agency/airline you book through and are valid for 30 days, but check ahead.

Getting around

If you’re staying in a hotel in Vedado or Playa you can grab a taxi to Habana Vieja for CUC$5-10 (£2.60-£5.30). Once there, the quarter is best negotiated on foot, although
a horse and carriage tour from the Plaza de San Francisco can be arranged for approximately CUC$30 (£16) per hour.

City information

The best source of on-the-ground information is at Infotur at 358 Calle Obispo , which sells excellent maps. For personalised city tours call by San Cristóbal Agencia de Viajes in Plaza de San Francisco. Its specialised Social Programs (CUC$10/£5.30) and Architecture (CUC$19/£10) tours are highly recommended.

Where to stay

Habana Vieja offers over a dozen meticulously restored colonial-era hotels run by Habaguanex, a company affiliated to the City Historian’s Office; prices range from the CUC$65 (£34) per night El Mesón de la Flota  to the exquisite CUC$240 (£127) per night Hotel Santa Isabel.

To really get under the skin of the city, you can opt to stay in a casa particular, a bona fide Cuban home where a family pays tax and is permitted to let out a maximum of two rooms to foreigners. There are dozens of casa particulars dotted around the Old Town and nightly room rates rarely exceed CUC$35 (£18.50). Find the best options on

Issues: what the future holds

Long free from the creeping tentacles of Western commercialisation, Cuba’s and Havana’s uniqueness is largely a result of the isolationist policies pursued by its long-standing president, Fidel Castro. But with the octogenarian leader sidelined by a recent bout of diverticular disease, the future of Cuba and its idiosyncratic culture hangs precariously in the balance.

In numbers:

95,400 Approximate population of Habana Vieja

900+ Number of buildings of historical importance in the Old town

81 Age of Fidel Castro

1862 year Bacardi set up his first rum distillery

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