There are numerous reasons why the Caribbean islands are incredibly popular, with the most popular reason being that they are the nearest tropical destinations for hundreds of millions of people who live in the eastern United States, Canada, and western Europe. Though the Caribbean weather is reliably warm every day of the year, there are some months that are far more popular than others.

In the article found below, we'll discuss each of the different time periods with the reasons you might want to visit alongside reasons you might want to choose another time. The best time to visit the Caribbean is probably whenever an island vacation fits best into your schedule, but for those with more choices the article below should help you sort things out.

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Here's the short version of this whole article

Because of the year round temperatures, you’ll find that the Caribbean is considered a great destination pretty much any time of the year. Another thing to note is that during the wetter season, both hotels and flights tend to be relativity cheap. On the other hand, the weeks of Christmas and New Years 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 offer guests lower prices, so those are the best value for people who want the best weather coupled with reasonable prices. The month of May through November is noted as 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 think it will be.

Best months for weather in the Caribbean: December through March

Since all Caribbean islands, aside from a few of the Bahamian islands, are located in the Tropics, you’ll find that they are warm every day of the year. This also means that instead of four seasons they only have two, which are known as the “dry season” and the “wet season.” December through March are part 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 the coldest months in the Northern Hemisphere where most of the visitors live and fly out of. There is something magical about boarding a plane in freezing temperatures and getting off that same plane in a perfect, warm, and 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’ll find that you are one of many. You might think that everyone else is with their families at home so you can have a resort to yourself, but that won’t be the case at all. Instead, you’ll find that 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, well in advance.

 

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. Because of this, you’ll want to book early so that you can still get a good deal. Those looking for a “last-minute bargain” will find that those are very hard to come by.


Advice for visiting the Caribbean during the holiday weeks

As airlines and resorts are well aware of this peak period in demand, you’ll find that they have no incentive to offer low airfares or room rates. This is 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 important to book your flight right away. This is the best way to ensure that you get a good deal.

 

Any other time of the year the Caribbean offers the lowest fares only two or three weeks out, as we discuss in this article on the cheapest times to book flights. But, when looking at these peak season weeks, the earlier you book the less you’ll have to pay. Weekend flights book first so if you can fly on weekdays, you’ll want to do so.

 

The most popular resorts with the best, and most positive, reviews also tend to book up earliest, so it can be a good idea to book a flight and hotel package at the same time. As long as you book your flight by July/ish you should be getting a pretty good deal, but earlier is always better so book as soon as you can even if it’s Autumn when you are reading this. As for hotels you could wait longer if you like to, but since most hotels allow you to cancel up to a few days before your stay for free, there isn’t a bad side to booking early.

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 listed above will give you the same Caribbean weather alongside much smaller crowds and lower prices on both airfare and hotels. The chance of tropical storms is very, very low and the chance of warm and sunny days is fantastic each day. Because the last few weeks of December are so popular, the weeks before and after serve as a small time period that offers an uncrowded and affordable vacation.

 

Many people aren’t quite ready for a sunshine getaway before Christmas, and if you’re in these group of vacationers then you’ll be happy to note that the weeks after Christmas can be perfect. This is 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 (and bigger) 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 a bit warmer. You’ll also want to note that during this part of the year, there is basically no chance of any tropical storms. You can also 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, which is exciting.

 

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

The Hurricane Season runs from June 1st through November 30th each year. But, if you look at the data for when Caribbean hurricanes generally occur, you’ll find that the actual hurricane season is a lot shorter. In fact, it generally runs from early August through late October.


Real peak hurricane season: August, September, October

September is the easily the busiest month for Caribbean hurricanes. Because of this, the possibility of a large storm is very real. If that 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

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 bunch of money by 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 even book a different return flight.

 

Since you’ll be saving at least 50% on your hotel room, you’ll be able to 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

What is nice about Tropical storms is that they 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 Islands of Aruba, Bonaire, and Curacao are just north of Venezuela and haven’t 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

Just a few short years ago the only “overwater bungalows” in the Caribbean were a few small eco-resorts off of Central America, but back 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.

 

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 completely 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 beautiful Jamaica resorts I wrote an article to help you decide if a Sandals stay is right for you.


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