The Best Time to Visit the Greater Antilles

The Best Time to Visit the Greater Antilles

The Greater Antilles are a group of islands in the Caribbean, most prominently consisting of Cuba, Puerto Rico, Hispaniola, and Jamaica. The Greater Antilles are warm year-round and always welcoming to tourists- except for June through September as this is the hurricane season when, generally, these islands should be avoided.

From Christmas until spring break, the Caribbean's largest islands are a busy place for families, with another boom in the summer holidays. The main hurricane season runs from late June to September, with major storms occurring roughly every ten years and rainfall persisting until November. In the winter, temperatures rarely fall below 20°C, making this the best time to visit Greater Antilles in the Caribbean Islands. 

Weather in the Caribbean

It’s no wonder that trips to the Caribbean are so popular, with its warm climate and gorgeous scenery. Choose a vacation spot anywhere in the region, and you can expect warm, sunny, and dry winter weather from December through March—the best time for a visit if you’re looking to avoid the rain. The rainy season begins in the summer months, which can be a good time for scoring discounts on hotels and flights. Or consider marking your calendar for mid-April to early June, when there’s less rain than during the height of hurricane season but low crowds and great prices.

Best Time to Visit Cuba

The dry, winter months from January through mid-March are considered the ideal time to visit Cuba, particularly Havana. Between June and August, the likelihood of rain greatly reduces, and the temperature averages 75 degrees Fahrenheit (23.9 degrees Celsius). Expect a flurry of activity in the city in August, when Carnival is taking place. When it comes to hurricane season, the best time to avoid visiting Cuba is from September through October.

Seasons in Cuba: Weather, Average Temperature, and Rainfall

January - mid-March (Winter/High Season)
Between January through mid-March, this is Cuba’s winter and is considered the best time to visit Cuba- especially Havana. There are comfortable temperatures between 65-75 ℉ (18.3-23.9 ℃) and little precipitation. The downsides are that it will be crowded and accommodations will be more expensive.

Late-March - mid-June (Spring/Off-season)
Most of March is still devoted to high season prices, but during April, May, and June, lodgings will be a lot more reasonable. The only significant downside is that there’s a high chance for rain during this spring season, and it is considerably warmer during this season, upwards of 80 ℉ (26.7 ℃). 

Late June - August (Summer/Hurricane Season)
Between June and August is a good time to visit Cuba. Although it’s hurricane season, you only need to worry about hurricanes affecting your trip to Cuba between September-October. During this season, the chance of rain decreases significantly, and the temperature rounds out a bit, averaging around 75 ℉ (23.9 ℃). Carnival is in August, so expect the city to be bustling.

September - December (Fall/Hurricane Season)
Between September and October, Cuba is most likely to be hit by a hurricane, and it’s not recommended to visit during these months. A ton of rain comes down during this season as well, with averages upwards of 70 mm. Most hotels won’t be open, but opening during this season will have excellent deals.

Best Time to Go to Puerto Rico 

Seasons in Puerto Rico: Weather, Average Temperature, and Rainfall

April - mid-June (Spring/Off-Season)
Puerto Rico can be visited at any time of the year, but the best time to go is between April and mid-June. The weather is warm during these months, and many of the winter crowds have gone home, but the wet season hasn’t started. Lodging will be extremely cheap during these months, and the extreme rains don’t begin until the end of June.

Late June - September (Summer/Hurricane Season) 
The summer is the height of the wet/hurricane season in Puerto Rico, but there are the best hotel deals during this season. Going during this season is a gamble because you may get rained on or have hurricane warnings every day you’re visiting.

October - mid-December (Fall/Off-Season)
In the fall, lodging prices should be reasonable as these are also considered off-season months. But the rain won’t be an issue, and the temperatures are consistently warm; this is an excellent time to visit.

Mid-December - mid-April (Winter/High Season)
These winter months are the high season in Puerto Rico because it’s still warm here, unlike most of the world. There are more crowds during this season, and hotels are more expensive, but the weather is still at great temperatures in the low 80’s ℉ (26’s ℃).

Best Time to Visit Jamaica

From mid-November through the middle of December, many people consider this the best time to visit Jamaica, owing to the great deals and reduced crowds. Around 75 °F (23.9°C) is the average temperature during this period. With the start of hurricane season on June 1, the likelihood of rain increases tenfold.

Seasons in Jamaica: Weather, Average Temperature, and Rainfall

November - mid-December (Spring/Off-season)
After hurricane season ends, it is considered by many the best time to visit Jamaica due to the impressive deals and lack of crowds. During this time, the temperatures are comfortable, and both lodgings and flights will be more affordable and available.

Late-December - March (Spring/High Season)
Spring is the high season in Jamaica. Beginning in late December, tourists start flocking to Jamaica to experience the beautiful beaches. The real downsides of visiting during this time are that flights and hotels will be a lot more expensive and there will be crowds just about everywhere you’re planning on visiting.

April - mid-June (Summer/Off-Season)
The average temperature stays about the same at around 75 ℉ (23.9℃), but the crowds and prices have dropped drastically. The downside of visiting during these months is that the chance for rain increases tenfold, with hurricane season officially commencing on June 1.

Mid-June - October (Summer/Fall/Hurricane Season)
In June, the Hurricane Season officially begins, which means flight and room rates will be the lowest annually. If you choose to travel during this season, expect rain, but there won’t be crowds, and the rates will be a lot lower. It’s recommended that you buy travel insurance for plane cancelations or delays if you want to visit Jamaica during this season.

Best Time to Visit Hispaniola (Haiti/the Dominican Republic)

Hispaniola (Haiti or the Dominican Republic) is at its best from November to April, when temperatures and humidity levels are just right. Lodging and airfare costs drop dramatically in the summer, but the likelihood of rain increases dramatically near the end of the season. It's official that hurricane season begins in June, but the worst of it won't hit until the end of July or early August.

Seasons in Hispaniola: Weather, Average Temperature, and Rainfall

November - April (Fall/Winter/High-Season)
The best time to visit Hispaniola is during these months. The temperatures are perfect, but it’s a little rainy at times, especially in the northern areas of Hispaniola, but the rain generally comes in short bursts that don’t last more than an hour. Additionally, the humidity will be pretty low when compared to other seasons, and hotel and flight rates won’t be outrageous during these months. 

May - mid-June (Spring/Summer/Off-Season)
During the summer in Hispaniola, the temperatures begin to get extremely hot. Although hurricane season doesn’t begin until June, a fraction of the rains are present, as more build-up towards the beginning of Hurricane Season.

Late-June - October (Summer/Hurricane Season)
The hurricane season in Hispaniola officially commences on June 1, but it’s not likely to be a problem until late July or August. During this season, lodging and flight prices go down drastically, and the chance of rain is very high, especially towards the end of the season.

Best Time to Visit Cayman Islands

Seasons in the Cayman Islands: Weather, Average Temperature, and Rainfall

The Cayman Islands are a fun location for beach-loving travelers who want to relax on the white sandy beaches. Sunny Caribbean weather during the month of April is perfect for those who enjoy outdoor activities like swimming and scuba diving but do not want to be too hot. December through March, known as the dry season, is when there is little chance of rain and plenty of sunshine. If you are looking to get on that plane, then try traveling in October or November when ticket prices are considerably lower than other times of the year.

Mid-April to mid-December (Off-season) - Off-season travel to the Cayman Islands, which typically runs from mid-April to mid-December, is a great time to save money, although summer tourism to the Cayman Islands has increased in recent years. Hotels, inns, and condos typically offer discounts ranging from 20% to 50% off their winter prices.

November to March (Winter/High Season) - During the winter months (November through March), the daytime temperature is 72–80 degrees Fahrenheit and the weather is often clear and tranquil. When a nor'wester blows through in the winter, it brings cool winds and rough seas to the north and west beaches. In the winter, you may want to bring a sweater or a light jacket to keep you warm.

September to October (Hurricane Season) - The increased probability of heavy rains and high temperatures in September and October make these months the least desirable for travel. As the Caribbean hurricane season officially begins in June and ends in November, September is the most dangerous month of the year.

Greater Antilles versus the Lesser Antilles, what's the difference?

Both the Greater Antilles and the Lesser Antilles are subgroups of the West Indies, which is a group of islands in the Caribbean Sea. The Lesser Antilles contain smaller archipelagos like the U.S. Virgin Islands, British Virgin Islands, Anguilla, Saint Kitts, and Nevis, Antigua and Barbuda, Dominica, Martinique, and Saint Lucia, Montserrat, Guadeloupe, Barbados, Saint Vincent, and the Grenadines, Grenada, and Trinidad and Tobago.

When it comes to size, there is a big difference between the Greater and the Lesser Antilles. The Lesser Antilles consists of numerous tiny islands that are smaller in size than their Greater Antilles counterparts. Moreover, the Greater Antilles is located at the northern end of the Caribbean Sea, south of the United States, while the Lesser Antilles is located at the southern end of the Caribbean Sea.

The best time to cruise the Lesser Antilles in the Caribbean is from January through May when afternoon rain showers are rare. As a result of its proximity to the equator and tropical temperature, all of the countries in the region enjoy a tropical climate with few big hurricanes. Find out more on our best time to visit the Lesser Antilles article. 


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