Hotel Nacional de Cuba

No hotel in the Caribbean carries more history than the Nacional. Opened in 1930 on the Taganana hill above the Malecón, its twin-towered eclectic façade has watched over every chapter of modern Cuban history: the mobster summit of 1946, the golden age of Sinatra and Churchill and Ava Gardner, the missile crisis—coastal artillery positions from 1962 still sit in the gardens—and the long decades since. Walking its Hall of Fame corridors, mojito in hand, is as close as travel gets to time travel.

It must be said plainly: the Nacional is a state-run monument first and a luxury hotel second. Rooms are simple and worn in places, service moves at its own rhythm, and travellers expecting international five-star polish should look to the newer competition. What the newcomers cannot copy is the atmosphere—the vast garden terrace above the sea wall, peacocks on the lawns, live son bands in the evening and the sweep of the Malecón curving towards the old city.

Stay for a night or two for the legend, take a garden-view room in the renovated sections, and treat the terrace at sunset as the main event. The Vedado location puts the hotel between the old town and the city's livelier modern districts, with taxis clattering past constantly. As an experience of Havana, rather than merely a place to sleep, it remains essential.