The Best Time of Year to Travel to the Caribbean

The Caribbean is a part of the world that’s synonymous with everything one could want from a holiday. The locations are beautiful, the weather is warm, and the food and drink are excellent. But, like any other tourist destination, some times of year make for better Caribbean trips than others.
If you’re considering a break in the Caribbean this year, then you’ll want to carefully weigh several factors, each of which can make the difference between a merely good holiday and a fantastic one. In particular, three questions stand out as worthwhile:
• What will the weather be like?
• How much will the trip cost?
• How busy will it be?

Let’s examine each of these considerations, and see what influence they might have on the quality of your trip!


The Caribbean’s climate forms a large part of its appeal – especially to brits who must endure slate-grey skies and cold rain for a considerable portion of the year. The region is famously tropical – which means that it enjoys considerable sunshine, as well as the occasional rainy spell. If you’d prefer not to spend your break seeking shelter from a never-ending monsoon, then you’ll want to go when the weather is driest. But perhaps a far more important consideration is humidity, which – unless your room is air-conditioned – will make getting to sleep at night difficult.




In this respect, it’s best to visit the Caribbean between December and April. Though the summer and autumn months are undoubtedly warmer, they’re also wetter, with frequent downpours and oppressive humidity that’ll make the heat seem all the greater. Late summer and autumn also sees the arrival of hurricane season; though the chances of your visit coinciding with that of a major storm are slim, such a coincidence will certainly impact your holiday if it does occur, and so it’s worth considering the possibility before setting out.


The favourable conditions of the Caribbean winter mean that the season is a boom for the tourist industry – and the price of accommodation can rise by as much as fifty percent in response to ballooning demand. The cost of flying over will also consume a significant chunk of your budget.

If you’ve got commitments at home to consider, then your options may be limited. Teachers, for example, may find themselves unable to get away during term time, and therefore unable to take advantage of the airline reduced fares.

If you’re looking for a compromise between favourable weather and manageable costs, then you might consider booking travel in either late May or early December – when the weather is not that much different to peak season. That way, you’ll be able to avoid much of the less favourable weather while still enjoying lower costs. In particular, the May Bank Holiday represents a great opportunity to get away and enjoy this part of the world without spending money unnecessarily.


The island nature of the Caribbean naturally has an impact on how tourists might enjoy it. It’s impossible to walk or get a bus from one part of the region to another, and so if you run out of things to do on one island, you’ll need to get a boat to another.

It’s for this reason that cruise ships are such a popular means of navigating the region. Rather than being tied to just a single island, you’ll be transported from one to another during the course of your stay – that way you’ll be able to see the maximum possible amount of stuff in a single trip.

You’ll want to time your cruise trip with extreme care. During peak times, cruise ships will periodically visit a port, causing that port to be quickly overwhelmed with passengers. During hurricane season, on the other hand, your ship might be prevented from getting into port at all!

On the plus side, on-shore activities are able to offer far greater variety than if you’d restricted your visit to just a single part of the Caribbean – you’ll be able to visit rainforests and coral reefs, partake in a huge amount of different watersports, and sample the local cuisine. Or, if you feel like sitting back and taking it easy, you can leave the rest of your shipmates to such things while you lounge on the deck.

If you find during your trip that there are some islands you’d like to spend more time with, then you’ll know exactly where to start planning your return to this famously beautiful part of the world.

In Conclusion

During peak periods between December and April, the Caribbean is at its best. But it’ll also be at its most crowded and costly. On the other hand, the hurricane season which runs from July to November will see the region’s wet weather come into play.

When planning your trip, you’ll want to consider either early December or late May – that way, you’ll be able to avoid the crowds (and the associated costs) while still enjoying fabulously warm and relatively dry weather.

Anguilla Beach