There really isn't a bad time to visit Havana. The hot, rainy season runs from May to October but winter (December to April) is the island's peak tourist season, when planeloads of Canadians and Europeans arrive in pursuit of the southern sun. Cubans take their holidays in July and August, crowding local beaches. Christmas, Easter and the period around 26 July, when Cubans celebrate the anniversary of the revolution, are also very busy. New Year's Eve coincides with the anniversary of Castro's troops marching into the city, so make hotel reservations early and plan to dance all night.
Havana, like the rest of Cuba, has two kinds of weather: hot and really, really hot. In July and August most of Havana goes on vacation to escape the sultry heat, which is bolstered by the humidity. The rainy season runs from May to October, overlapping with the hurricane season, which is generally from June to November. Havana can very occasionally be affected by cold winds from the North American interior, causing a day or two of temperatures below the 10°C (50°F) mark. Bring warmer clothes for the evenings if you are visiting at this time of year - it's colder than you think.
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