Caribbean islands are incredibly popular because they are the nearest tropical destinations for hundreds of millions of people who live in the eastern United States and Canada as well as western Europe. The Caribbean weather is reliably warm every day of the year, but some months are far more popular than others.

In the article below I will discuss each of the different time periods with the reasons you might want to visit along with reasons you might want to choose another time. The best time to visit the Caribbean is probably whenever you can get there, but for those with more choices the article below should help you sort things out.

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The Caribbean can be a good destination any time of the year because the temperatures don’t change much and hotels+flights can be much cheaper during the wetter months. The Christmas and New Years weeks are the busiest and most expensive weeks all over the Caribbean, and the weather is nearly perfect.

 

The periods just before and after this holiday period have the same weather and lower prices, so those are the best value for people who want the best weather and reasonable prices. The month of May through November are the slow time of year and the wetter months as well. Savvy travelers know they can get outstanding deals during that period and the rain usually isn’t as much of an issue as most people fear.

Best months for weather in the Caribbean: December through March

Since all Caribbean islands (except for some of the Bahamas) are in the Tropics, they are warm every day of the year. This also means that instead of four seasons they have only two, which are the “dry season” and the “wet season.” December through March are parts of the dry season all over the Caribbean, so visitors don’t have to worry about storms and they probably won’t get any rain either.

 

Another reason these are the most popular months is that these are obviously the coldest months in the Northern Hemisphere where nearly all of the visitors live. There is something magical about boarding a plane in freezing temperatures and getting off that same plane in a perfect, warm, sunny climate.

Busiest and most expensive time in the Caribbean: Late December

If you’ve considered going to the Caribbean in late December then you are not alone. You might think that everyone else is with their families at home so you can have a resort to yourself, but the exact opposite is true. Generally speaking, from the weekend before Christmas through the weekend after New Years, every seat on every plane is full and every hotel room in desirable resorts are completely booked.

 

Since so many people have time off work during that period, it’s by far the most popular time to head to the Caribbean, and as a result airfares and room rates are at their annual peaks. The good news is that if you book early enough you can still get a decent deal. Those looking for a “last-minute bargain” will usually be disappointed and choosing among the places that other people passed on.


Advice for visiting the Caribbean during the holiday weeks

Because all of the airlines and resorts are well aware of this peak period in demand, they have no incentive to offer low airfares or room rates because they know they can book everything eventually. Now that some low-cost airlines such as Southwest and jetBlue are serving the Caribbean, it’s best to book your flight as early as possible for the best fares.

 

Any other time of the year the Caribbean actually has the lowest fares only two or three weeks out, as we discuss in this article on the cheapest times to book flights. But for these peak season weeks, the earlier you book the less you’ll likely have to pay. Weekend flights book first so if you can fly on weekdays you’ll have a better chance of getting a decent deal.

 

The better resorts with the best reviews also tend to book up earliest, so it can be wise to book a flight+hotel package at the same time and just get it over with. As long as you book your flight by July or so you should be getting a pretty good deal, but earlier is always better so book as soon as you can even if it’s October when you are reading this. As for hotels you can afford to wait longer if you like, but since most hotels allow you to cancel up to a few days before your stay for free, there isn’t a good reason to wait.

Best bargain periods with the best Caribbean weather

  • December 1 through the weekend before Christmas
  • January 10 through the end of February

 

The two periods above will give you the exact same perfect Caribbean weather along with much smaller crowds and lower prices on airfare and hotels. The chance of tropical storms is basically zero percent and the chance of warm and sunny days is almost 100% each day. Since so many people are trying to head to the Caribbean for those last weeks of December, the weeks before and after that period are surprisingly uncrowded and affordable.

 

Many people aren’t quite ready for a sunshine getaway before Christmas, but the weeks after can be perfect because the weather at home tends to be even worse in January and February than it is in December, so the difference will feel even better once you step off the plane. You can get surprisingly good deals, but it’s still best to book as early as possible for the best airfares and the most choices of hotels.

Also great Caribbean months: April and May

While the best Caribbean weather combined with the worst weather back home is from December through March, the Caribbean weather in April and May is only slightly warmer and there is still almost a zero chance of any tropical storms. You can get great deals on airfares and hotels during this period, and unlike the other high season periods you can even get some good last-minute deals in April and May.

 

Especially with airfare it’s always best to start researching well in advance and if you are going to fly on Southwest or jetBlue or another low-cost carrier the fare will be lowest the earlier you book. But if you are flying in on American, Delta, or United you might actually see a drop in fares only two or three weeks out for these months.

Official “hurricane season”: June through November

Technically speaking the Hurricane Season runs from June 1 through November 30 each year. But if you look at data for when Caribbean hurricanes actually occur you’ll see that the actual hurricane season is much shorter and generally runs from early August through mid to late October. Before or after that period there is a tiny chance of a hurricane or tropical storm, but it’s not really the same as the traditionally active period mentioned above.


Real peak hurricane season: August, September, October

September is the single busiest month for Caribbean hurricanes so if even the possibility of a large storm scares you then definitely do not book a trip in September. August and the first three weeks of October are the next busiest periods and most people are better off avoiding those months as well unless you are close enough to book cheap flights in and out and can get a great deal on a resort stay.


That said, the hurricane risk is far overblown

Getting hurt in a hurricane or even having a vacation ruined by a hurricane is a bit like how many people are afraid to fly even though they know it’s the safest form of transport by far. When we are in situations where we have no control over tragedies (like flying or being in a major storm) some of us develop irrational fears.

 

The reality is that the number of tourists hurt in major Caribbean storms in the last 10 years is a very tiny number, especially compared to the millions of visitors in the so-called Hurricane Season. Weather watchers know about hurricanes at least a week before they get to popular Caribbean islands, so they are nothing like tornados or earthquakes that can appear spontaneously. In other words, if you get extremely unlucky and there is a big storm headed to your island when you’ll be there you will always have time to cancel or book an earlier flight out. The airlines don’t want to fly in those storms so they move flights around to get everyone out in time.


Buy travel insurance if you go to the Caribbean in hurricane season

Realistically speaking the chances of being in the path of a storm even in September are under 1% for any given person on any given week on any given island. You’ll save a lot of money traveling during that period so it’s probably worth buying a travel insurance policy with some of your savings that will reimburse you if you have to cancel or book a different return flight.

 

Since you’ll be saving at least 50% on your hotel room, you can easily afford 5% more for a travel insurance policy with generous benefits if there is a storm. Not all policies cover these things so it’s important to do your research before you buy one.


Islands with virtually no hurricane risk

Tropical storms tend to follow predictable patterns and there are actually a few islands that have almost no risk of being in the path of one. The so-called ABC Island of Aruba, Bonaire, and Curacao are just north of Venezuela and none has had a hurricane visit in well over 50 years. Barbados and Trinidad and Tobago are in this same area and also come with a near-zero chance of being in the path of a major storm.


Overwater bungalows in the Caribbean

Only a few years ago the only “overwater bungalows” in the Caribbean were a few small “eco-resorts” off of Central America, but in 2016 the high-end all-inclusive Sandals resort chain opened three excellent groups of overwater bungalows at different resorts in Jamaica and St. Lucia. They aren’t cheap, starting at over US$2,000 per night, but that is for high-end all-inclusive with 24-hour private butler service for each overwater bungalow, so you get a lot for your money.

 

You can get much more information on our main article on overwater bungalows in the Caribbean, and deeper information on these pages:

 

 

Again, it’s very important to factor in that the Sandals resorts are totally all-inclusive and unlike most other resorts they include top-shelf alcohol and even many activities such as water skiing and boat tours.

 

After visiting the Jamaica resorts I wrote an article to help you decide if a Sandals stay is right for you.


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