The mystery of Cuba has only been heightened by its off-limits status to Americans. Even though the travel ban has been loosened somewhat, the country still holds a great deal of mystique to travelers from all countries. The island is evocative of classic Cadillacs, jazz, cigars and old men playing dominoes. Those visiting Cuba should be prepared for an adventure, and should research travel plans in advance--in particular, when to go.
The busiest travel times to Cuba are Christmas, Easter, July and August; there are downfalls to visiting during these periods--airfares are much higher, the country is more crowded with tourists and it can be uncomfortably hot during late summer. Unless there is a specific occasion for you to visit at these times, it is best to venture forth during the off-season, when there are fewer tourists and the weather is a bit more mild.
The best time to visit Cuba is during the early months of the year, especially if you can manage to avoid the Easter holiday. Avoiding peak travel times yields an altogether more pleasant experience, since the crowds are considerably smaller and the weather is more temperate. Travelers should be wary of traveling later in the year, as the chance of hurricanes increases significantly.
If you want to travel for a festival, consider timing your trip around Havana's International Jazz Festival, which is generally held in February (one of the more optimal times to visit). The festival, which was initiated in 1978, has grown to become one of the premier showcases of jazz music with a plethora of world-class performers such as Dizzy Gillespie and Chucho Valdes.
