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There are few places in the world that wholly match your pre-trip daydreams of them — but Cuba most certainly will. The American classic cars are there, the hulking Buick Skylarks and Chevrolet Bel Airs that rumble through the streets of Havana beneath faded murals of Che Guevara and Fidel Castro. Those streets are as you hoped they might be: crammed with elegantly decaying colonial buildings, with lines of laundry hanging between them and elderly Cubans sat chewing the fat on the front steps, enormous cigars wedged between their teeth.

Outside of Havana you’ll bump along unpaved roads between fields of tobacco and sugarcane, passing campesinos on horseback who’ll raise their straw hats in greeting. You’ll wander the cobbled streets of dusty old towns, and be invited by locals to share coffee and stories in the shady courtyards of their homes. And when the heat finally drains out of the day, you really will have that night you fantasised about — drinking rum in wood-panelled bars and dancing salsa with a stranger till dawn. And for every longed-for trope you tick off, there will be a dozen unexpected ones too. Cuba is a country that meets and confounds expectations. The only certainty is that you’ll be planning to return before you’ve even left.

Main photo: The colourful buildings of downtown Havana (Alamy)

When it comes to things to do in Cuba, every trip should begin in Havana. All of life is played out on the streets here, from the musicians parading in the elegant plazas of Habana Vieja to the kids thwacking baseballs between the crumbling buildings of Habana Centro. To soak it all up, simply strike out and see where your feet take you. From the capital, follow a circular route, first heading west to the home of Cuba’s tobacco industry, Viñales. Emerald-green tobacco fields blanket the region, punctuated by rearing limestone stacks, groves of banana palms and thatched farmhouses. It’s best explored by bike, and there are plenty of places to hire them.

Emerald-green tobacco fields blanket the region, punctuated by rearing limestone stacks and groves of banana palms

Next, swing east and take your pick from a host of beautifully preserved colonial towns, among them the sleepy Spanish settlement of Trinidad, the good-time city of Santiago de Cuba, birthplace of the country’s son music tradition, and handsome, pastel-hued Cienfugos. Before you return to Havana, wind down with time on the beach. The cays off the north coast in Matanzas province have all the white-sand beaches and sapphire waters you could dream of.

Can I go to the US if I’ve been to Cuba?

Not that long ago, the only accommodation available in Cuba were drab state-run hotels or the spare bedroom in a private home, or casa particular, often rented out illegally. With the relaxation of restrictions around private business and international investment, the hotel scene recently got a lot more exciting. The choice now ranges from rural B&Bs to oceanside resorts and the most design-conscious boutique hotels.

The most character-laden option is often the casa particular. Enterprising home-owners have enthusiastically flung open their doors across the country, and a stay in one allows guests to peek into some extraordinary heritage buildings and experience Cuban hospitality at its finest. You might find yourself sleeping in a 17th-century villa, complete with frescoed ceilings and wrought-iron balconies, or a colonnaded farmhouse, with breakfast taken on the veranda with three generations of the family.

Big beach resorts exist along the coast, they’re generally a little less inspiring — but have all the facilities you’d expect from international chains. For a stay with a little revolutionary flavour, take a look at the storied Habana Libre in Havana — the hotel was home to Fidel Castro after he captured the city in 1959 and was allegedly the site of one of the many assassination attempts on him by American plotters.

It’s safe to say that, up until a few years ago, no one came to Cuba for its cuisine. With the state controlling its food supply, a decent meal tended to consist of a portion of flaccid chicken accompanied by dry rice and beans. With the loosening of regulations and the flourishing of private enterprise since 2005, all that’s changing. Paladares (home restaurants) are at the forefront of the food revolution, serving inventive dishes using newly available ingredients in often intriguing buildings. Seafood and fish are particular highlights (look out for bonita tuna, red snapper, grilled octopus and freshwater shrimp). A rise in the quality and availability of produce has meant good things for Cuba’s national dishes too, including ropa vieja (shredded beef with vegetables), ajiaco (a complex stew) and spit-roast pork.

It’s wildly disputed, but La Bodeguita del Mar in Havana claims to have invented the mojito

The drink most synonymous with Cuba is the mojito. It’s wildly disputed, but La Bodeguita del Mar in Havana claims to have invented the refreshing mix of white rum, lime, mint and sugar. True or not, this is still an atmospheric place to sample the drink. You’ll be in good company — the bar counts Fidel Castro, Gabriel Garcia Márquez and Ernest Hemingway among its previous patrons.

The site of a political prison may not seem like the most obvious place to spend a holiday, but it’s one of the many reasons why you should add the Isla de Juventud (Island of Youth) to your itinerary. A bouncing three-hour catamaran ride from the mainland, the island takes the already laid-back Caribbean pace of life down a notch or two. The enormous prison, Presidio Modelo, is now a haunting museum and is well worth a dig around, but most people come for a spot of scuba-diving.

It’s surprising how little fanfare diving in Cuba gets given its clear waters, untouched reef and abundant marine life — Isla de Juventud has all that plus a couple of shipwrecks to explore. Back on dry land there are plenty of white-sand beaches on which to flop — with the promise of a daiquiri at a rum shack and another spectacular sunset to end each day.

Winters are warm, dry and popular. Avoid crowds and seasonal price hikes by travelling in spring, but give busy Easter a miss. Hurricanes can hit from June to November. As of January 2021, the only legal currency is the Cuban National Peso (CUP). You shouldn’t take it into or out of the country — on arrival, convert euros or sterling (avoid US dollars) at banks, official Cadeca exchange offices and big hotels. There are also (sometimes unreliable) ATMs in larger cities. Before you arrive, apply for a tourist card at the embassy or via an online visa service, valid for 30 days’ travel.

Take me there

Inspired to visit Cuba but yet to book your trip? Here are the best packages from Tui* and Caribbean Warehouse*. These are the best tours of Cuba from our trusted partners*.