Cuba is one of the few countries where the clichés are all true and miss the point simultaneously. The 1950s American cars in improbable colours are real. The son cubano on street corners at midday is real. The crumbling colonial buildings in turquoise and ochre and pink are real. The rum is good and available everywhere, and the mojito above the Malecón as the sun drops into the Caribbean is the platonic ideal of the mojito — every other version trying to describe this one without having tasted it. All real. And then Cuba turns around and shows you something else, and something else again, and you realise the clichés were the entrance hall and the house is considerably larger than the door suggested.

Havana: The Most Complicated Love Affair in Travel

Havana is a city of extraordinary, slightly heartbreaking beauty — the architecture of what was once the wealthiest city in the Caribbean, now in magnificent decay, the salt air and tropical heat producing a palette no designer could replicate. Old Havana is the densest collection of Baroque and neoclassical architecture in the Americas — cathedrals, plazas, convents, and palaces around interconnected squares that give it a human scale most colonial centres have lost. Wander it slowly in the early morning before the tours begin, when the light comes through the narrow streets at an angle that makes every facade look painted.

The Malecón — the eight-kilometre seafront boulevard that runs along the northern edge of the city — is where Havana conducts its social life after dark. Couples, teenagers, families, musicians, fishermen: all using the seawall as a shared living room in the particular way that cities with warm evenings and limited indoor entertainment have always organised themselves around the free and available. Sitting on the Malecón at night with a bottle of Havana Club and the city behind you and the Caribbean in front is one of the great free urban experiences in the world.

Trinidad: The Town That Time Preserved Instead of Forgetting

Three hours east of Havana by bus, Trinidad is the colonial town that Cuba’s economic isolation accidentally preserved in amber. Built on sugar money in the 18th and 19th centuries, its centre of cobblestoned streets, pastel-painted townhouses, and ornate Baroque churches reflects the extraordinary wealth generated by the sugar industry before abolition, and has survived largely intact because the investment that would have modernised it never came. This is the specific Cuban paradox — the same economic conditions that created genuine hardship also preserved an architectural heritage that would have been replaced elsewhere by concrete and commerce. The result is one of the most beautiful small towns in the Caribbean, and one of the most genuinely complete time-capsules in the Americas.

The Casa de la Música in Trinidad’s main plaza — live salsa from nine in the evening until the musicians decide otherwise — is the best free music venue in Cuba, and Cuba has considerable competition for that title. Climb the bell tower of the Iglesia Parroquial Mayor at sunset for a view of the terracotta rooftops and valley beyond that justifies the three-hour bus journey on its own terms.

Practical Notes for the Newly Arriving

Cuba operates a dual currency system that has been simplified in recent years but still requires attention. Bring cash — American cards do not work, European and Canadian cards work inconsistently, and the ATM availability outside Havana is unreliable enough to make cash the only sensible strategy. The casa particular system — private home accommodation, equivalent to a B&B, where you stay with a Cuban family — is significantly better than most hotels at every price point and puts your money directly into local hands, which is the most meaningful thing your tourist dollars can do in a country where the economics of travel are politically loaded.

Learn ten words of Spanish before you arrive. Not because Cubans are unfriendly to non-Spanish speakers — they are extremely friendly to everyone — but because the ten words will open doors that stay closed without them, and the doors that open lead to the Cuba that is considerably more interesting than the Cuba visible from the tour bus window.

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Cuba is complicated and beautiful and unlike anywhere else. Go before it changes too much in either direction. It is already changing. The window is open. Use it.