Visit Trinidad During...
High season vs. Low season
In Cuba the high season for tourism is from November until April. The best time in terms of weather is from December to April, as it's just after rainy season and just before the scorching temperatures of summer arrive. However, accommodation is likely to be more expensive and tourist attractions more crowded.
Low season lasts from May to October and is a good time to look for deals on air fare, hotels, etc. There are less tourists, which means short - if any - lines, less crowded beaches, etc.
Festivals & Celebrations
At the beginning of January Trinidad hosts the Trinidad Cultural Week (Semana de la Cultura Trinitaria), a week-long arts festival featuring traditional music, performances exhibitions, regional crafts and more. It coincides with the anniversary of the city's establishment centuries ago.
In June, Trinidad celebrates its local Carnaval for three days, during which the city is bursting with all the elements of the Caribbean Carnaval of popular imagination: conga dancing, parades, music, drinks, etc.