Cuba
Cuba is not a smooth destination, and that's rather the point: a country of crumbling grandeur, extraordinary music and genuine warmth, where the logistics take effort and the rewards are entirely human.
December–June lands in winter for Cuba: warm, sunny weather ideal for the coast; prime hiking and outdoor season with the trails and passes open; calm seas and swimmable water.
Havana
Give Havana at least three nights. Habana Vieja is the restored colonial core of plazas and cathedral squares; Centro Habana next door is unrestored, loud, and where the city actually lives; Vedado has the 1950s hotels, the Malecón sunset and the best live music.
Fixtures: the Malecón at dusk, a son or timba night at the Fábrica de Arte Cubano or Casa de la Música, the Museo de la Revolución for the state's own telling of the story, and a slow walk down Calle Obispo. A vintage-car tour is touristy and also, honestly, a lot of fun.
Beyond the capital
Viñales, three hours west, is the tobacco valley: limestone mogotes, ox-drawn ploughs, horse rides between farms and cigar-rolling demonstrations that are less staged than you'd fear. Two nights.
Trinidad, on the south coast, is the best-preserved colonial town in the Caribbean: cobbles, pastel houses, live music on the church steps every night, with Playa Ancón nearby and the Valle de los Ingenios behind it. Cienfuegos is a French-founded elegant stop en route.
For beaches, Cayo Coco / Cayo Guillermo and Varadero are the resort strips; Playa Girón and the Bay of Pigs offer better snorkelling and a fraction of the people.
The practicalities that actually matter
Bring cash in euros and plan to spend it. Foreign cards are unreliable and US-issued cards do not work at all; ATMs are scarce. Budget more cash than you think and keep small notes.
Stay in *casas particulares - licensed family guesthouses. They're better value than state hotels, dramatically better for food, and your hosts will arrange the next casa, taxis and meals. Shortages are normal*: fuel, bottled water, medicines and menu items all come and go. Carry a basic pharmacy and a water filter bottle.
Internet runs through Wi-Fi hotspots and patchy mobile data via an ETECSA tourist SIM. Treat the trip as semi-offline and it becomes a feature. Getting around: colectivo shared taxis and Viazul buses between cities; renting a car is expensive and fuel queues are long.
When to go
December to April is the dry season and the best weather: warm, low humidity, though Christmas and Easter are busiest and priciest. May to June is a good shoulder. August to October is hot, humid and inside the Atlantic hurricane season.
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