The Best time to visit the Caribbean, explained

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.

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.

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.

• 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.

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.