Best and Worst Time to Visit the Caribbean

The Caribbean islands have it all – scenic beaches, wondrous marine life, hikes ending in spectacular viewpoints, mouthwatering food, and festivals that greet and see off tourists every year. But to enjoy all that, you need to time your visit carefully.

For those who want to make the most of the sea, beach, and sun, the best time to visit the Caribbean is between December and May, which is the dry season. The period from June to November is the rainy season and is accompanied by storms and unpredictable weather.

Of course, there are other factors you may want to consider, like crowds, festivals, and activity-specific schedules. Let’s dive into the details.

The Best Time to Visit the Caribbean in Terms of Weather

The Caribbean covers a large territory of about 1,063,000 square miles (2,753,000 square km), so weather does vary by region. However, one thing is for certain: all the islands have a tropical climate. This means that temperatures range from mid-70s to mid-80s Fahrenheit (around 24-30 degrees Celsius) throughout the whole year.

However, whether it’s the dry or rainy season will make a big difference to your experience.

During the dry season (December to May), you get lots of sun, no rain, and little wind. The rainy season (June to November), on the other hand, is less predictable, with heavy rainfall, storms, and unpredictable hurricanes. There have been cases of category 5 hurricanes that wreak havoc on the islands, like Hurricane Irma or Hurricane Lee.

Keep in mind that there are exceptions to the timeline. In Turks and Caicos, for instance, the rainy season begins earlier – in May.

In general, we’d recommend avoiding the Caribbean during September, which seems to be the most dangerous month for potentially violent storms.

The Best Time to Visit the Caribbean to Avoid Crowds

The peak of the tourist season in the Caribbean is between December and February. People from the Northern Hemisphere choose the coldest months of their winter to visit the sunny Caribbean and escape the bad weather back at home.

Additionally, islands such as St. Lucia and St. Vincent and the Grenadines have their festivals that coincide with the end of the dry season: either in May or June. These festivals draw huge crowds to the islands. To avoid that, you should check the festival calendar of the island you want to visit (more on the festival season later).

But, the Caribbean islands are mostly tourist-free during the rainy season. If you’re really looking to avoid crowds, book your dates between June and November. However, make sure you check the weather forecasts beforehand and comply with the local authorities’ warnings regarding the weather.

The Most Affordable Time to Visit the Caribbean

“Affordable” refers to two different things in our context:

• The affordability of the local shops, restaurants, bars, and lodgings;
• The affordability of flight tickets.

 As you’ll see, these two differ dramatically.

If you want to enjoy discounted prices at both regular hotels and the most luxurious resorts, the best time to visit the Caribbean is during the rainy season, between June and November. You can even eat delicious local dishes for less than half the money you’d spend to make it at home.

Yet, there’s a problem with visiting the Caribbean during the rainy season, and we are not just talking about the weather. During the rainy season, the prices of plane tickets go up because there are very few flights. Plus, the weather conditions can contribute to flight delays and cancellations or cause turbulence – which not everyone’s a fan of.

Moreover, most of the smaller Caribbean islands don’t receive international flights during the rainy season. If you want to visit one of those islands, you’ll need to board a charter plane or book a boat or ferry to that island.

However, storms and big sea swells make charter flights and sea trips difficult, too. So, although the rainy season is more affordable once you’re on the island, the transportation itself might cost you more than you bargained for.

Conversely, flights are much cheaper during the dry season – when tourists flock to the islands – but hotels and restaurants are much more expensive during this time.

The Best Time to Visit the Caribbean for Boat, Snorkeling, Diving, or Hiking Tours

The best time for fun activities in nature and in water are during the peak tourist season, meaning December to April.

During that period, you can swim alongside sharks in the Bahamas, whales in the Dominican Republic, and stingrays in Antigua. You can scuba-dive inside the world’s first underwater sculpture park in Grenada, and snorkel over magnificent coral reefs in the Cayman Islands.

In more detail:

• Giant creatures such as sharks and whales are mostly seen on the shores of the Bahamas and the Dominican Republic between January and March.
• The month of January is the best time to view colorful little fish visiting the coral reefs of the Caymans or Virgin Islands. This is when the water is at its clearest and most azure.

Most of these tours take place on boats, and the locals only offer boat tours during the dry season, when the weather conditions are sail-friendly. Similarly, the land tours mostly take place during the dry season because the roads and trails aren’t in great condition during the rainy season. Landslides are just one of the dangers during this time.

The Best Time to Visit the Caribbean for Festivals

Almost all the islands in the Caribbean have their own festivals. Most of these festivals take place towards the end of the dry season (or, you may call it the tourist season) or at the start of the rainy season as a sort of farewell to all, but there are exceptions to that rule such as Aruba.

Here, we list some of the most noteworthy festivals in the Caribbean, when they take place, and what you can expect from them:

• Anguilla Summer Festival: The Anguilla Summer Festival typically takes place on the first Monday of August and lasts for a week. People in gorgeously colorful costumes take to the streets, dance to old African rhythms, and walk around the vivid bazaars. Locals also do some boat racing, which is a sight to see.
• Aruba Carnival: Aruba is the carnival central of the Caribbean, and the official governance website says the carnival season starts in November and goes on until March. But the peak of the carnival is between January and February, with lots of catchy music and wild dances on the streets. People from all ages, genders, sexual orientations, and backgrounds express themselves through their costumes and cadences.
• Barbados Crop Over: The Barbados Crop Over festival isn’t so much a carnival as it is a series of joyous events that explore the flora, fauna, and history of the island. From the end of May until mid-August, you’ll see parades, live music, exhibitions, dancing, and ceremonies all over the island.
• Bahamas Eleuthera’s Junkanoo Festival: This particular festival in the Bahamas is a mixture of local dances, costumes, and delicious native food. For 2024, the festivities are scheduled between January 10 and 14.
• British Virgin Islands (BVI) Emancipation Festival: Like all the emancipation festivals in the Caribbean, this one takes place between mid-July and mid-August. You’ll find yourself surrounded by a parade, dancing to live DJ performances, watching boat races, and rooting for your favorite fisherman in the Fisherman’s Tournament.
• Carnaval Dominicano: This Dominican Republic carnival is a celebration of the country’s independence, starting at the first Sunday of February and concluding at the Independence Day, February 27. Although the republic gained its independence in the late 19th century, the festivities actually go back to the 16th century, as a life-affirmation event for the natives. In these festivities, you’ll see lots of ominous costumes such as devil masks, which the locals use to make fun of colonialists. Of course, there’s also lots of music and dancing, so get ready to wear your dancing shoes when confronting the colonial past.
• Carnival Saint Lucia: The Saint Lucia carnival that takes place in the first three weeks of July is famous for its pageants. There are also calypso competitions and beach parties.
• Saint Lucia Jazz and Arts Festival: The 2024 Saint Lucia Jazz and Arts Festival is scheduled from April 30 to May 12, and that period is when it typically happens every year, drawing talented artists and musicians from all around the world.
• Saint Kitts and Nevis National Carnival: The Saint Kitts and Nevis National Carnival has less emphasis on parades, pageants, and costumes but more on drinking, partying, live music, and dancing. So, you’ll probably be moving and drinking a lot!
• Trinidad and Tobago Carnival: The Trinidad and Tobago Carnival lasts only two days – the Monday and Tuesday before Ash Wednesday (six and a half weeks before Easter). And yet, those two days are enough to earn the label of “the greatest show on earth.” During this period, you’ll see lots of wild parties, stick-fighting events, reenactments of historic milestones from the country’s past, a thousand drums beating in unison, and buoyant, audacious, and sometimes spooky costumes.

Key Takeaways

In a nutshell, the best time to visit the Caribbean islands in terms of weather, fun activities, and cheaper flights is during the dry season, December to May. The best time to avoid crowds and get cheaper accommodation is the rainy season, June to November. However, violent storms and expensive, infrequent flights make the rainy season much more of a gamble.