3-Day Havana itinerary – Explore The City Of Decaying Grandeur

Under the crumbling buildings, Havana pulses to swinging music and clinking cocktails. A city with a modern edge and a fascinating history. Here’s our 3-day Havana itinerary.

On first glance, you could be forgiven for thinking Havana is frozen in time. Buildings of prior colonial masters crumble into varying states of decay. Vintage cars from bygone eras rumble down battered lanes. Weary and weathered, any attempt at civic maintenance was abandoned long ago.

Yet, within the old laneways, Havana feels like a young city. A town rejuvenating itself on whatever resources it can get its hands on.

Bruised facades display the street art of a new generation conflicted over Cuba’s political past and communist present. Imperial Spanish architecture hides cool cafes and quirky shops. Industrial buildings hum to the familiar sounds of Cuban jazz and cocktail bars buzz above minimalist contemporary art galleries. Even the colourful vintage cars that beguile tourists are born out of necessity. A vamped up and long maintained remnant from enforced economic sanctions.

On our first visit, our impressions of Havana were steeped in intrigue and surprise. It’s a warm welcoming city that beats to the rhythm of its own drum. Spending 3 days in Havana is all about understanding its political history and absorbing the cool relaxed vibe of a city finding its feet.

Here’s all you need to help plan your own Havana itinerary.

DAY 1 AM / EXPLORING HAVANA’S OLD TOWN AND CATHEDRAL

Strolling Havana’s old town is the highlight of a trip to Cuba’s capital. Start the day with breakfast at whitewashed Café Bohemia, tucked under arches in a tiny arcade just off Plaza Vieja. It’s a beautiful square surrounded by magnificent colonial buildings.

If you only pop into one make it the photographic exhibition of Cuba’s past at the Fototeca de Cuba.

PLAZA DE SAN FRANCISCO DE ASIA

Next, amble up to the 16th century wonkily-cobbled Plaza de San Francisco de Asia and into the beautiful Plaza de Armas. The leafy green interior of Havana’s oldest square is overlooked by imposing grand architecture. The most magnificent is Palacios de los Capitanes Generales. It houses a range of artefacts detailing the history of the city and is well worth exploring.

CASTILLO DE LA REAL FUERZA

Next, walk past the Castillo de la Real Fuerza, to the Cathedral standing at the end of another attractive square. Built in the 18th century it looks more like a fort than a church with its castellated exterior and austere interior.

CENTRO DE ARTE CONTEMPORÁNEO

Just around the corner check out the throng of tourists lining up for overpriced cocktails at La Bodeguita del Medio, one of Hemingway’s drinking joints. Then, pop into the Centro de Arte Contemporáneo Wifredo Lam, a small gallery dedicated to one of Cuba’s most famous painters.

DAY 1 PM / UNCOVERING THE REVOLUTION & CUBAN STREET MUSIC

For lunch try the hubbub of restaurants on Calle Aguiar, a narrow pedestrian lane with tables spilling onto the street. Refreshed, head into the Museum of the Revolution. It’s heavy on pointless detail and the information boards are confusing, but it gives a fascinating insight into how history is interpreted by the victors and how propaganda continues to be used to support the regime.

CALLE OBISPO – CALLE MERCADERES

Next, as the afternoon slowly comes alive with the sound of music, head back into the old town and explore the shops, museums and galleries of Calle Obispo, Calle O’Reilly and Calle Mercaderes. But don’t leave it there, head into the back streets where the buildings are in even worse condition and the atmosphere much the better for it.

CAFE EL DEL FRENTE

As the evening settles in, enjoy some of the Havana nightlife. Head up to the rooftop bar Café El del Frente. Their huge tasty cocktails quickly make an impact so be careful coming back down their narrow staircase.

For dinner settle into Nao Bar. Tapas never tasted so good thanks to the old-school band entertaining patrons from the tiny lane outside. Alternatively, try Monserrate Bar which serves local food in a sultry Caribbean bar while a surprisingly good five-piece band swoons from a tiny stage.

DAY 2 AM / LEARNING ABOUT CIGAR MAKING IN A WORKING FACTORY

For breakfast head to El Dandy, a Havanan institution perched on pretty Plaza del Cristo. Its food is good, but the wall-to-wall photographs of boxers and ballerinas regaling Cuba’s artistic past are the real drawcard.

HOTEL INGLATERRA

This morning’s goal is to go to the Real Partagas Cigar Factory. But Cuba does not like to make things easy, so the tickets are sold a 30-minute walk away at Hotel Inglaterra. It’s a beautiful building with an imposing neo-classical façade. The tickets are on sale at the tourist desk in the reception.

GRAN TEATRO & CAPITOLIO NACIONAL

From the hotel it’s only a short taxi ride, but it’s better to take the half-hour walk. Stroll past the grandiose Gran Teatro and Capitolio Nacional before heading into the backstreets around Calle Maloja and Calle Sitios.

This is a very old part of town, with atmospheric crumbling buildings, evocative art and colourful murals. The whole place buzzes with local life and a distinct lack of tourists.

REAL PARTAGAS CIGAR FACTORY

The tour of the factory is only 45 minutes but it’s a fascinating insight into both the making of cigars and the communist economy. Cigars are a very artisan product with every step in the process completely handmade. You will see workers strip the leaves of veins, carefully roll the cigars, pick the best ones and box them before presenting their handy work for inspection. It may look like harsh conditions but these are skilled workers in desired jobs which pay twice that of a doctor or three times that of a teacher.

No Havana itinerary is complete without a cigar so pop around the corner and pick up one at the Romeo and Juliet Cigar shop.

DAY 2 PM / LEAFY VEDADO & AGEING BUENA VISTA SOCIAL CLUB LEGENDS

Havana is not just the old town; it’s a big city with a number of faces. Leafy Vedado is an attractive suburb worth exploring. Hop in a taxi and make for the Necrópolis Cristóbal Colon.

PLAZA DEL LA REVOLUCÍON

ON the way, get the taxi driver to stop for a couple of minutes at the Plaza de la Revolución. There’s nothing much to see here (except tourists) so take the obligatory photo of the huge mural of Che and jump back in the cab.

NECRÓPOLIS

The Necrópolis (cemetery) is a remarkably beautiful and relaxing place. A million miles away from the hustle and bustle of the old town, magnificently adorned graves reveal vignettes of Cuba’s past. A helpful map with a suggested itinerary is provided on entry.

COPPELLIA ICE CREAM

There are many lunch places tucked into the backstreets of Vedado but Belview ArtCafé is one of the best. A relaxed space with a leafy terrace, high ceilings and smatterings of avant-garde art. Spend the afternoon exploring Vedado with its grander houses and a better standard of living. Pop into John Lennon park, grab an ice cream at state-run Coppelia: and drink with the young and the cool at Rampa 23 or Cine Yara.

BUENA VISTA SOCIAL CLUB

Buena Vista Social Club is a thing of the past in Havana. But the closest you get is an evening at Legends del Guajarito in the old town. Here the great and good of years gone by are wheeled out to perform on stage. It’s very touristy and really very cheesy. But, nothing gets your nostalgic groove on like watching 70 and 80-year-old Latin American Emmy winners still holding a tune. Make sure you get the drinks and show tickets and not the expensive dinner tickets. The food is terrible.

DAY 3 AM / PERUSING CRAFT STORES AND ART GALLERIES OF THE OLD TOWN

After the show last night, the final day of your Havana itinerary might involve a slower start. So rise late, and head to cool modern El Café for breakfast. Try the pulled pork and yucca and hipster coffee.

PHARMACY MUSEUM – RAFAEL TREJO BOXING CENTRE

Now make a loop around the southern part of the old town collecting the beautifully presented Pharmacy Museum, the stalls of the San José Almacenes Artisanal centre and the Rafael Trejo Boxing Centre. Cuba has won many Olympic golds for boxing and it’s a firm part of their makeup.

NUESTRA SENSORA DE LA MERCED

If you get lucky the church of Nuestra Senora de la Merced will also be open allowing a look at its fine interior and cloister.

Although the sites are a bit thinner in this part of town, that’s not really what Havana is about. Amble past more crumbling walls, revolution-supporting murals, old antique cars and locals selling whatever they have.

MUSEO NACIONAL DE BELLAS ARTES

With the afternoon heat rising ensconce yourself in the air-conditioned Museo Nacional de Bellas Artes. It has two sections, but the best is the one focused on Cuban art. Start on the top floor for pre-revolution art before heading downstairs to the post-revolution gallery. You’ll soon get a feel for what is (and what isn’t) acceptable methods of portraying the communist regime.

DAY 3 PM / TOURING IN AN VINTAGE CAR & CHILLING IN FÁBRICA DE ARTE

For more insight into the interaction between Cuban literature and the revolution, head a few blocks east to Museo Lezama Lima. Lezama was appointed director of the National Council of Culture by Fidel Castro in 1959.

However, he soon found himself out in the cold after his epic book Paradiso (mainly written in this building) portrayed a homosexual encounter and used religious imagery. Both of these things were anti-ethical to the communist regime.

MALECON

With the sun setting take a stroll along the Malecon before picking up a taxi to head across town. You could get a standard taxi, but better to pay a bit more and do a 1-hour open-topped tour in a vintage car, finishing at El Cocinero for dinner.

This trendy restaurant is set in a restored factory. The outdoor terrace is located on the roof and serves well-prepared food in a cool atmosphere. Even better than the food is the bar set inside one of the ruined chimneys, the next floor up. Seats are perched on a balcony winding around a tiny bar outside. It’s a pricey place but well worth the cost.

FÁBRICA DE ARTE CUBANO

After finishing dinner head next door to Fábrica de Arte Cubano. This maze of a venue has bars, art installations, and multiple live performances. It could be a mess, but its high-quality art and super cool vibe see it packed to the rafters every Thursday to Sunday. It’s also one of the coolest Salsa Clubs in Havana.

WHERE TO STAY IN HAVANA

For most of your 3 days in Havana, you’ll be exploring the atmospheric streets of the old town. However, a few of the attractions and museums are located in the inner suburbs. So, we recommend booking accommodation in the northwestern section of the old town.

It’s a nice part of Havana with good facilities and it allows you to walk into the centre and also access Vedado and the attractions a little further away.

Booking a homestay, or Casa Particulares is a good way to get some insider knowledge and have an authentic experience. However, in Havana, it’s also possible to book a nice hotel – something not that common in other parts of the country.

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BOOK BEFORE YOU GO

Not much in Havana needs booking in advance. But if you want to go to Legends del Guajarito for just drinks and the show then drop them an email before you fly. You should also make a reservation for dinner at El Cocinero in Vedado. It’s a long way to drive to find they are full.

If you like to get organised before you go, here are some tours you might be interested in.

GETTING TO HAVANA

International flights to Cuba are more expensive than most places and less regular so it is worth playing with your travel dates. Shop around and look for cheaper indirect options if possible. Flights arrive at Aeropuerto Internacional José Martí. You will need a tourist visa and proof of medical insurance to enter.

If you’re American it’s even trickier, check the latest information here.

You cannot bring cash into the country but the airport has a number of ATM, banks and CADECAs (money exchange desks). Taxis to the town centre are CUC30 which your accommodation will be able to arrange for you, otherwise, metered taxis wait outside.

GETTING AROUND HAVANA

The public bus system is notoriously difficult to navigate, so it is best to either walk or take taxis. During the day taxis between any two places in the town centre should be about CUC10, rising to CUC15 at night. It may be a little more if you head to the furthest reaches of Vedado from the old town).

It’s worth taking an open-air antique car at least once. But line it up to actually get somewhere you want to go, otherwise, you’ll pay a lot for a little bit of touristy bling.

HAVANA ITINERARY MAP

We’ve put this itinerary together in the order we think you should see things to collect as much as possible over your 3 days in Havana. All the sights we listed are included on this map.

BEST TIME TO GO TO HAVANA

Havana is baking hot in the summer so you want to avoid that. Plan to be in Havana in the dryer and cooler months of winter. December to March are ideal with a warm tropical heat that’s not too oppressive. Avoid the Christmas holidays if possible.

Even in winter, Havana can be a bit of a scorcher, so this itinerary has been planned to avoid melting in the heat of the day as much as possible. Most afternoons are spent in air-conditioned comfort somewhere, with minimal walking between places.

MORE CUBA READING

Cuba is a unique place. Years of Soviet-funded political ideology created a strong- if slightly confusing – sense of national identity. Soviet, American, Spanish, Caribbean and African influences fuse together to create a fascinating place to visit. Here is some more of our reading about this fascinating place.

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