Simple answer is anytime, and I'm not being flippant. Different seasons however offer various benefits that may be more appealing based on your individual interests. This time of year (summer) provides multiple opportunities to engage in Jamaica's traditional culture since we literally celebrate our independence from the start of July to the end of August. Visit our site for http://www.jamrockjourneys.com/events/ for a few examples. The world renowned Reggae Sumfest provides Jamaica's Reggae and Dancehall in its purest form. Most Jamaican's gain financial success by touring internationally, ironically they generally perform less in Jamaica, and so when they do, it is a big deal. The audience is also unforgiving, so the artists bring their A-game. As a result of the collective culture, beats and rhythms are shared among various artists. The beat for a song is often created before lyrics are put to it and multiple artists will make songs off of a single rhythm. So in Jamaica lyrical content and ability to deliver that message in an entertaining way is what sets you apart. Reggae Sumfest is that stage where the best talent is showcased. All of that to say, if you are a Reggae Buff then you go this time of year with the added benefit of the National Festivals, such as the Festival Song Contest, and Plays that is all part of the independence package.
The fares and hotel rates are also cheaper because it is considered the low demand season. You also can find fruits such as ackee, mangoes and guineps this time of year. The downside is that June through November coincides with the hurricane season. Many hotels however give you a "raincheck" to return at no additional cost or low cost in the future if the rain simply ruins everything. The good thing is that even when it rains, the sun usually follows right behind it which leads to the bigger challenge- the heat and humidity. If you have hiking in mind, Blue Mountain may not be the best during the hurricane/rainy season because as you get closer to the peak it will be misty and cool. Most attractions, however, are enjoyable year round and anything you wanted to do outdoors is likely to be available any time of year.
The winter (December –March) is peak season and most tourists travel during that time of year. Because Jamaica is playing host to guests this time of year you will have a harder time finding empty beaches if you’re looking for a more laid back setting. You can get around this by vacationing in the south or east coast where tourism is not as developed. Winter is favored by most guests because it provides a break from the cold in their home countries. Most visitors are from North America, Britain and Eastern Europe. This in itself is a neat time to experience Jamaica with people from other countries. While fruits are not as abundant (you can still get your basic oranges, banana, sugarcane etc.), the insects are also out less since it is a little cooler. The downside is that the rates of resorts and hotels are higher given the higher demand. In December and January you can still experience Sting, Rebel Salute, and Jazz and Blues Festival if music is your thing.
In the end no matter when you choose to go you’ll have a ball. Your decision then is influenced by your budget, interests and weather preference. If you want to spend a little less, like it extremely toasty, love music and want to see traditional culture with not too many other tourists in sight go between June and November. If you want it slightly cooler (relatively since it will still be warm considered you will be leaving from freezing temperatures to tropical weather), enjoy the music and culture, but spend a little more and enjoy it with other international guests then go between December and April. April can bring rain showers so bear that in mind. The history and culture is so rich, the people so laid back and accommodating, the food so delectable, the atmosphere so vibrant that you are guaranteed to find something that you will enjoy. Jamaica is one of those places that have a lot of hype around it, and it actually lives up to the hype. If you do all-inclusive you’ll have fun but you definitely want to venture off and mingle with the people because they are who makes Jamaica what it is in my mind. That’s the whole reason we started Jamrock Journeys, to give people a taste of the way of life as Jamaicans experience it.