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What Are The Best Times To Cruise The Caribbean?

The Caribbean is a great destination for first-time cruisers, family cruisers traveling with kids, romantic honeymooners, and just about anyone else who loves fun in the sun. But, what are the best times to cruise the Caribbean? Trying to figure that out can be tricky. 

Not surprisingly, the best time of year to cruise the Caribbean depends on your priorities. December through to April is great if you’re looking for the driest weather, though this is peak season. Meanwhile, June to November can be one of the most affordable times of the year to visit the Caribbean, but it’s also hurricane season.

Read on to learn the key facts to guide your decision so that you can have the best possible cruise vacation for your needs. 

The Big Picture

There are pros and cons to cruising the Caribbean no matter which part of the calendar you’re looking at, and there’s a wide range of factors that can come into play.  But, in general, there are a few things to consider when choosing the best time of year to book your Caribbean cruise. Notable factors include price, locale, and weather (particularly hurricane season). Other factors include school holidays and peak travel times.

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December through April is considered the high season, thanks to warm weather and holiday season breaks. However, this is also generally when the weather is at its best, with less chance of hurricanes. The weather is typically warm and sunny during this time, making it ideal for cruising. This is an excellent opportunity to escape the cold farther North.

But, prices will be higher than usual due to the peak season. Also, crowds may be an issue at popular destinations such as St. Kitts, Jamaica, the Bahamas, and Cozumel. Cruising during these months also means you’ll be able to enjoy popular Caribbean events like Carnival.

May through November is considered the low season, so prices will be lower but there may be more risk of bad weather.

What Are The Best Times To Cruise The Caribbean | photo of Oasis of the Seas docked at Nassau
Royal Caribbean’s Oasis of the Seas moored in Nassau Harbour near Paradise Island (Bahamas).

The shoulder season is an excellent time of year to book. Late April and May, and November to early December, see cruises that are not as busy or as pricey and with still relatively good chances of fabulous weather. This is a wonderful time to book in general. 

What Are The Best Times To Cruise The Caribbean If You Care About Location? 

The “Caribbean” is a very big place with hundreds of islands spanning over a million square miles. From a cruising perspective, there are three main zones — Eastern, Western and Southern. Each region has its own unique culture, history, and activities, so passengers who prefer one region over another can choose a cruise that aligns with their interests.

Here are a few key differences between Eastern, Western, and Southern Caribbean cruises in a nutshell. 

Eastern Caribbean cruises typically visit islands like the Virgin Islands and Puerto Rico, as well as smaller islands, such as St. Maarten, and Antigua. The Eastern Caribbean generally has more British and French influences.

Western Caribbean cruises visit bigger islands, such as Jamaica and Cozumel. And, it’s a great itinerary for those looking for a party atmosphere with plenty of beaches and activities.

Southern Caribbean cruises often are a little longer and typically stop at more ports, including Aruba, Bonaire and Curacao, Trinidad and Tobago, Barbados, St. Lucia, and Antigua.

The Southern Caribbean is known for its lush vegetation and rain forests, as well as its scuba diving, snorkeling, and eco-tours.

Southern Caribbean cruises are typically hotter and more humid than the other two options, while Western Caribbean cruises can be quite cool, especially at night. Of course, this varies depending on the time of year you go, but it’s something to keep in mind if you’re looking for a particular climate.

The best times to book for Eastern Caribbean cruises are December to April. For western Caribbean cruises, December until March is the peak season. Southern Caribbean islands are best cruised over the summer months, from July until September. The weather is good, and they are not generally severely hit by hurricanes. 

Saint Lucia, Caribbean Islands

What Are The Best Times To Cruise The Caribbean If You Care About Price? 

Given that the peak season is December through April, the cheapest times to cruise the Caribbean are anything but these months! Typically, the low season occurs over the summer and autumn months, during hurricane season. 

You may think that sailing during hurricane season is a terrible idea, but usually, that’s not the case. It is usually pretty safe to sail during this time, and you can get some great bargains on cruises for this period. The cheapest and best time to sail is probably at the very beginning or end of hurricane season. There are fabulous prices, and your risk of encountering bad weather is still reasonably low. Islands such as Aruba and Curacao are rarely threatened by hurricanes, and Aruba has never experienced a direct hit.

For more tips on making the most of your cruise vacation dollars, check out our post on top ways to stretch your family cruise dollars.

What About The Weather?

There are a few different things to consider when deciding on the best time of year to cruise the Caribbean. The weather is generally warm and sunny year-round, so that’s one thing you don’t have to worry about. However, hurricane season runs from June to November, so if you’re hoping to avoid any chance of bad weather, you may want to plan your cruise for outside of those months.  

From a weather perspective, the best time to cruise the Caribbean is during the shoulder months of April, May, October, and November. The weather is typically milder during these months, and there is less chance of hurricanes. However, school holidays can make cruising during these months more expensive and crowded.

What About Hurricane Season?

While we’ve seen the devastation that hurricanes have wreaked on parts of the Caribbean in recent years from the safety of our own homes, the last thing we want is to be caught in one. Hurricane season usually runs from the beginning of June until the end of November in the Caribbean, peaking from mid-August. However, not all parts of the Caribbean are affected by hurricanes in the same way.

The eastern Caribbean tends to see hurricanes at the beginning of the peak season, so from mid-August. On the other hand, the western Caribbean islands experience peak season for the entire stretch of the hurricane season. You are least likely to experience hurricane issues if you’re sailing in the southern Caribbean.

If you thought cruising in hurricane season was a terrible idea, you might want to think again. Hurricane season sees the least amount of traffic during the year, so it is a great time to explore if you don’t like crowds and want a bit of space to enjoy your destinations. You’ll get the lowest fares but may not be guaranteed perfect weather, with the chances of rain and storms higher than usual. Because the chance of experiencing rough seas can increase, if you are prone to motion sickness you should take steps to avoid seasickness.

Cruise ships also rarely get affected by hurricanes. Unlike a tornado or tsunami, hurricanes usually don’t sneak up on you. Typically, there’s sufficient warning that cruise lines can make itinerary changes to avoid the projected path of a hurricane. Scientists can predict hurricane paths several days in advance. Also, the captain and crew have sophisticated instruments to detect hurricanes early enough that they would be able to steer the boat on a path around the worst weather. Experiencing some rougher waters is a possibility, but the crew would typically charter a safe path for the boat. 

If you’re thinking of booking a cruise during the hurricane season, booking towards the end of November is a good option.

Pros And Cons Of Cruising In Hurricane Season

So that you know it’s possible to cruise with relatively low risk during hurricane season in the Caribbean, what else should you know? There are pros and cons of choosing this time of year to cruise. 

There are pros and cons to taking a Caribbean cruise during hurricane season. On the pro side, prices for cruises are often lower during this time of year. Additionally, many people find the weather during hurricane season to be more tolerable than during the hotter months. On the con side, there is always the risk that a hurricane could disrupt your cruise plans. If you decide to take a Caribbean cruise during hurricane season, be sure to purchase travel insurance in case you have to cancel or change your plans.

Beach in stormy weather


  • Cruise fares are lower
  • Fewer people book during this time – both the ship and the ports on your destination islands are likely to be less crowded.
  • It is summertime, and the weather is warmer than usual
  • Sailing the southern Caribbean this period almost eliminates your chances of hurricanes


  • Your itinerary could change based on the weather
  • Rough waters
  • Potentially canceled cruises

Tips For Sailing During Hurricane Season 

  1. Be flexible, both on your timings and your destinations
  2. Buy travel insurance
  3. Take seasick tablets with you if you’re prone to that – you could encounter rough waters.
  4. Keep your eye on the weather forecasts in the days leading up to your cruise.


No matter what time of year you would like to cruise the Caribbean, you’re likely to have a great time in the sunshine with palm trees and clear skies. Even during the hurricane season, cruises depart and are rarely canceled. Pick your ideal time of year based on where you want to go, how busy it will be and your budget.

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