In terms of the weather, Trinidad is always warm and variations in seasons are small. The rainy season is June to November and the dry season December to May. November and December are generally the coolest months, the end of dry season can be quite hot (April, May) and also August often has some hot weeks. Rainy days are often cooler, but the dry period is better if you would like less mosquitoes.
The 40 Days period, between March 26 and May 5, is always a special period to go. In this retreat period there is an intensive program with more morning talks, workshops or conversation groups than usual. A few weeks before the 40 Days we celebrate Maha Shivratri, a program of chanting in honor of Shiva during the night from 9 pm to 6 am the next morning. If you can catch this festival, it will be well worth it! Maha Shivratri is a different date each year, check our calendar or google it.