Is there a bad time to visit Cuba? Our answer would be no, as anytime is better than never getting there. High season tends to be from December to March – especially with the Canadians trying to get away from their cold winter weather. August to September is the hurricane season for the Caribbean so some try to avoid traveling then – but availability & prices are the best during these months (well after the school holidays). If you can avoid school holidays really nice times to visit are April/May & November to mid-December.