Havana 5-day Itinerary

This twin-towered 18th-century masterpiece of Cuban Baroque, with beautiful undulating facade and mismatched bell towers, dominates Old Havana’s main plaza. Peek inside: the altar is made of Carrara marble and Italian frescoes crown the altar recess.

Cuba’s most impressive museum, housed in two separate buildings almost next to each other, showcases the best of Cuban art (in one building) from the 1600s to the modern day, and international artists over 5 art-filled floors of a second building.

Americans poured into capitalist Cuba in the 50s bringing with them the latest consumer goods and beautifully finned cars.

Going for a spin in a classic, chrome-festooned gelato-coloured Chevy, Dodge or Ford – preferably a convertible – is one of the highlights of any trip to Havana.

Tourists are not permitted to drive classic cars themselves; instead, Gran Car’s vintage vehicles are dotted throughout the city, often outside the big hotels, and easily recognisable as the vehicles in the best condition on the streets.

Known as ‘Havana’s sofa’, the Malecon, an 8km stretch of sea wall on Havana’s waterfront, is where lovers, friends, musicians, swimmers and fishermen crowd before dusk to enjoy the cooler hours.

Swing your legs over the wall with a bottle of rum, or just lean against the wall with your back to the sea to chat to locals and enjoy the stunning light on the architectural line-up that curves around the Atlantic-facing sea road.

The best way to experience Cuban cuisine, international dishes, and hospitality is to eat at a paladar – a private restaurant run by Cuban entrepreneurs. Hundreds of such private restaurants (paladares) have opened in the last 2 decades years across Havana.

Initially restricted to mom-and-pop outfits – in private homes and limited to only 12 chairs, a recent relaxation of the rules has seen these small-scale restaurants expand to fill entire homes (e.g. Otra Manera) or open in dedicated venues.

On the menu you’ll now find simple and elaborate seafood dishes, ropa vieja (shredded beef or pork and veg in a tomato-based sauce), roasted suckling pig, Cuba-made goats’ cheese, chicken Kiev (in the one Russian paladar) and Chinese dumplings (made by a Tianjin chef).

Emerging out of the tattered shell of a handsome mansion is Havana’s most famous restaurant. (It starred in a well-known Cuban movie). Come for the building, food, ambience, and drinks on the rooftop terrace.

Winston Churchill puffed on Romeo y Julieta, Che Guevara on Montecristo, and Fidel Castro’s favourite smoke was a Cohiba.

Cuban cigars are famous around the world. There’s a reason: it’s the combination of a perfect blend of tobacco plant terroir in southwestern Cuba, the climate, and the 200 artisanal processes that crafts a cigar from its tiny beginnings as a pinhead-sized tobacco seed to luxury smoke.

There are around 40 cigar factories in Cuba, with Partagas – one of the biggest – offering tours on weekday mornings.  This is a unique chance to see the cigar-making process in one of the very few Havana factories open to the public.

Legendary American writer Ernest Hemingway downed a record 16 daiquiris in one sitting at this, his favourite Havana bar. The bartender mixed him a sugarless and double rum tipple and named it the Papa Doble. Come early to bag a barstool at the glamorous scarlet bar.

This funky, Cuban-run cafe and coffee roastery in Old Havana is a popular stop. It sells arguably Havana’s best coffee, great breakfast and exceptional sourdough sandwiches including ample vegan and vegetarian options.

In the decades spanning the 16th and 18th centuries, Cuba’s Spanish rulers built a series of imposing forts to repel rampaging buccaneers from raiding the Spanish treasure fleets in the Bay of Havana, and to fence out the English. Five hundred years on, these muscular fortresses still dominate Havana’s harbour, and have come to symbolise the city – they even appear on the city’s coat of arms.

El Morro Castle, and its lighthouse, is the most iconic and the city’s emblem. This impressive stone and coral fort, complete with cannons, defended the eastern headland of Havana Bay from pirate attacks until the end of the 18th century, when the British captured the city.

The fortress houses a display on the Italian engineers and builders of the castle. You can also climb the 19th-century lighthouse for a view of the city and Malecón.

American novelist Ernest Hemingway lived at this hilltop farm just outside Havana for 20 years. His fishing boat, library, books, writing tower, clothes, pet graves and his now empty pool are preserved for fans of his life and literature.

Havana’s best fine dining experience. Mediterranean dishes with a light Cuban touch are served up in a minimalist space fashioned out of a modernist mansion.

History buffs will love the Museo de la Revolución that details the minutiae of Fidel Castro’s 1953-1959 rebel campaign, culminating in victorious revolution in the ornate surrounds of the old Presidential Palace. The outdoor exhibition displays weaponry, aeroplanes and the Granma yacht, which brought Castro from exile in Mexico to Cuba to relaunch the rebel campaign in 1956.

Invigorating, percussion-driven and sexually charged rumba, a dance rooted in the Congo and slave history, developed in the late 19th century in Havana and is still widely performed.

A number of live venues across Havana offer rumba sessions: the most colourful is in the open-air mural-covered Hamel alley; the most varied is at El Palenque where other musical varieties are also performed. The least touristy is at the crowded El Jelengue de Areito.

Raulito Bazuka’s old-school paladar format is updated by the smart surrounds and the wonderful food – Cuban and international flavours. Raulito was mentored by chefs at a Michelin-starred restaurant in Spain.

Dating from the 19th century, Havana’s remarkable cemetery is an architectural gem, home to marble mausoleums, winged angels, sparkling mosaics, wrought-iron motifs, Art Deco sculptures, vast government monuments and 1959 Revolution memorials.

The Fábrica de Arte Cubano is a creative powerhouse of art, photography, music and dance. All the hot stuff is inside this converted peanut oil factory with food and drinks to fuel the night. Uber popular.

This imposing wedding-cake mansion is the seat of the Cuban government. Stop by to see the marble 400ft Hall of the Lost Steps, the gigantic Statue of the Republic, the bronze bas-relief front doors, and the statue of the devil in a patio devoid of shade.

This Havana landmark – a huge, vanilla-hued confection looming above the sea – is the city’s most storied building. From its opening in 1930, it has hosted Olympians, presidents, Hollywood stars and mots notoriously perhaps, the Mob. Johnny ‘Tarzan’ Weissmuller dived into the Nacional pool from his room, and the Mob dined on roast flamingo during their 1946 Mafia conference.

The hotel has a unique and extraordinary history, and offers excellent daily guided tours. These fascinating tours divulge the gossip on the famous guest list, delve down into tunnels buried in the gardens dug by the government during the tense days of the 1962 Missile Crisis, and end in the ‘Hall of Fame’ – a room decorated with hundreds of photos of famous guests on the walls.

An emerging district of street art, galleries and festivals in Southern Old Havana. Look out for cool street art, Galería Taller Gorría, and new bars and cafés.

An insightful primer on Cuba’s sugar cane and rum-making in a grand 18th-century mansion, with gorgeous stained-glass windows. Tour highlights include the working model and train of the erstwhile Cuban Hershey sugar plantation, a whiff of the base ingredient of rum – molasses – and a tasting session in the museum bar.