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These are the best times to visit the Caribbean

Jan. 09, 2020
8 min read
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Comprising more than 7,000 islands with distinct cultures, activities and scenery, there's a lot to consider when planning a trip to the Caribbean. Luckily, the tropical climate is fairly consistent year-round, which means it’s difficult to find a bad time for an island escape.

When you go should depend largely on your personal travel goals. Do you want to score the cheapest flights possible, experience a specific event or escape the frigid winter temperatures of the north? To help determine when you should start planning your next getaway, read this guide to some of the best times to visit the Caribbean.

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When to experience the best weather in the Caribbean

While the temperatures in the Caribbean remain fairly consistent — between the mid-70s and mid-80s throughout the year — the climate is considered “tropical marine,” meaning seasons are broken into wet and dry. The wet season usually begins in May or June and lasts through late November. The remainder of the year is considered the dry season.

Typically, mountainous regions, such as the Blue Mountains of Jamaica, receive more rainfall than flatter destinations like Aruba. This means that the likelihood of having to endure an afternoon shower can vary greatly even within a single island. With that being said, Turks and Caicos, Aruba, Anguilla, Bonaire and the British Virgin Islands tend to be drier overall, while Puerto Rico, Antigua, St. Lucia, Barbados and Grenada tend to be wetter.

The Blue Mountains of Jamaica. (Photo by © Rick Elkins/Getty Images)
The Blue Mountains of Jamaica. (Photo by © Rick Elkins/Getty Images)

Like most tropical climates, average daily temperatures rarely fluctuate more than a few degrees between summer and winter. The Cayman Islands, Aruba and Curaçao trend on the warmer side by Caribbean standards, meaning you may want to keep them on your radar for a winter escape. Puerto Rico, the Dominican Republic and Turks and Caicos tend to be cooler.

It’s also important to consider the trade winds (especially when visiting islands in the southeast Caribbean, such as Puerto Rico and the British Virgin Islands), which blow northeast and are most prevalent in the winter, resulting in a wind chill factor. So, save for travelers hoping to dial in their windsurfing skills or enjoy a cool breeze while sitting on the beach, stick to the northern and western sides of the islands during the winter months.

Traveling during hurricane season

Hurricane season in the Caribbean typically stretches from June 1 through Nov. 30, with the majority of storms striking between September an October. But that by no means should deter you from visiting the Caribbean during this time.

Related: 7 tropical spots to visit before hurricane season hits

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If you're traveling during hurricane season, just pay attention to weather alerts and be strategic about picking a destination. Some islands, such as those in the southeast — Aruba, Curaçao, Barbados and Grenada, to name a few — have very little risk of being affected.

Saint George-Harbour, Grenada. (Photo by Westend61/Getty Images)
Saint George-Harbour, Grenada. (Photo by Westend61/Getty Images)

When to visit the Caribbean to avoid crowds

As you can imagine, peak hurricane season — September and October — is a slower time in the Caribbean. But the slow season actually starts around May, with the sweltering summer heat, and extends through hurricane season. This is a great time to not only avoid crowds, but also find some great deals for an affordable vacation.

Tourism starts to pick up just before the holidays, and usually lasts through spring. This is also the region’s driest season, and travelers can expect reliable sunshine and warm temperatures.

When to visit the Caribbean for events and festivals

If you're hoping to experience a festival or event in the Caribbean, there's almost always something going on — you just have to make sure to choose your destination accordingly.

Originating in Trinidad and Tobago, each island hosts its own Carnival (sometimes called Carnaval), which is usually a big street festival with its own distinct traditions. No matter the month, there's almost always a Carnival taking place somewhere in the Caribbean. But there are also plenty of other cultural and music events you can experience during a trip to the Caribbean.


In addition to its beaches, Jamaica is also famous for reggae. Fans should plan to visit during Jamaica’s Reggae Sumfest in Montego Bay. Each year, local and regional acts like Beres Hammond, Buju Banton and Chronixx perform over the course of six nights. During the event, expect plenty of beach parties and concerts.

Damien Marley at the Reggae Sumfest. (Photo by Shelby Soblick/Getty Images)
Damien Marley at the Reggae Sumfest. (Photo by Shelby Soblick/Getty Images)


It’s not just anywhere you can find an entire festival dedicated to a single species of mollusk. But that's exactly what happens every November in Turks and Caicos. When it started in 2004, the the Conch Festival's main purpose was to use the island’s national symbol and main export — conch — to draw visitors to Blue Hills, which is Providenciales’ oldest settlement. Now, local restaurants showcase their nontraditional takes on a traditional favorite, as live music and a Carnival-like atmosphere take over.

(Photo by Tetra Images/Getty Images)
(Photo by Tetra Images/Getty Images)


The Trinidad, or “Trini” Carnival, is the genesis of all other Carnivals throughout the Caribbean. The exact date changes each year, but it's always held on the Monday and Tuesday before Ash Wednesday. At 4 a.m. on Carnival Monday, the streets are flooded with paint-covered Carnival-goers during J’Ouvert, or “day open." Parades, music and festivities continue until Ash Wednesday.

(Photo by Sean Drakes/LatinContent/Getty Images)
The Trini Carnival in Trinidad. (Photo by Sean Drakes/LatinContent/Getty Images)


Each spring, the Saint Lucia Jazz Festival hosts some of the biggest names in modern jazz, with performances held against breathtaking landscapes and indoors at more intimate venues. In addition to live performances, professional development workshops and classes, participants get to experience Saint Lucian culture, which is replete with dance, food, parties and festivities.

(Photo by Earl Gibson III/WireImage/Getty Images)
The Saint Lucia Jazz Festival. (Photo by Earl Gibson III/WireImage/Getty Images)

Cheapest time to visit the Caribbean

September is the cheapest month to book accommodations across the Caribbean, according to travel search site Kayak. Prices vary by location, but median hotel rates will set you back around $209, compared to the $360 you might expect to pay in December. September also happens to coincide with peak hurricane season, so depending on where you're headed, be prepared for some potential afternoon showers.

Winter is also when should expect to find standard and peak nights for award redemptions. Think: One-night stays at the Category 8 St. Regis Bahia Beach Resort in Puerto Rico from between 85,000 and 100,000 points per night, versus 70,000 off-peak award nights in September.

Cash flights to many destinations in the Caribbean are cheapest between January and March, according to Skyscanner. Of course, airfare depends on when you book, your point of origin and your destination.

If you're flying to Montego Bay (MBJ) from New York City, Los Angeles or Chicago, for example, February is a safe bet for cheap flights. Flights to Turks and Caicos from New York City are the least expensive in January, but February is more affordable for travelers based in Los Angeles and Chicago. Flying to the Dominican Republic? If your trip originates in either New York City or Chicago, plan your trip in March to score a solid flight deal. But if you’re coming from Los Angeles, you’ll likely find cheaper flights in January.

Bottom line

It's a lot more challenging to find a “bad” time to visit the Caribbean than a “good” time. In fact, some may argue there's no bad time to visit at all. Even hurricane season, despite its challenges, can be a great time to plan your tropical vacation, especially if you're flexible about the exact destination.

Featured image by (Photo by thomas lefebvre/Unsplash)