Havana, on foot and slowly. The restored squares of Habana Vieja are the obvious part; what makes the city is the walk between them — along the Malecón at dusk, and through Centro Habana, where the buildings are held up by props and the entire life of the place happens in the street.
Viñales. Limestone mogotes rising straight out of tobacco fields, oxen still doing the ploughing, and drying barns you can walk into. The most beautiful landscape in Cuba and the easiest to get into, on foot or on a horse.
Trinidad. A sugar town that stopped in about 1860 and stayed that way — cobbles, pastel houses, and behind it a valley of ruined mills that the UNESCO listing covers as well.
Shore diving at Playa Girón. The wall is a short swim from the beach, the cenotes are inland, and it costs a fraction of what diving costs anywhere else in the Caribbean. That it happens at the Bay of Pigs is the strangest part of it.
Santiago de Cuba. The other Cuba — closer to Haiti than to Havana in feel as much as in distance, with the best carnival in the country in July, and the cemetery where both Martí and Castro are buried.
Baracoa. Over the mountains at the far eastern end, reached by a road built in the 1960s because there had never been one. Cacao, coconut, rivers, and a way of cooking unlike anywhere else on the island.
The music, wherever you are. Not the hotel show. The Casa de la Trova in any provincial town on a weeknight, where the audience is local and half of them can play.
A 1950s car on a long road. Not the polished convertibles on the Prado, but a battered Chevrolet running the Havana–Viñales route with six people in it and a Soviet diesel under the bonnet.