Best Time to Cruise to the Caribbean

Best Time to Cruise to the Caribbean

Best Time to Cruise to the Caribbean

While cruises sail worldwide, many travelers favor the Caribbean, and for a good reason. Caribbean cruises sail year-round, allowing travelers to explore white sand beaches anytime. If you’re booking a cruise to the Caribbean, you may wonder the best time to visit. Since the Caribbean experiences wet and dry seasons, some months of the year are preferable to others. If you’re spending the time and money to cruise down South, make sure you go when it’s best for you.

Learn about the best times to cruise to the Caribbean before planning your trip.

In This Article

What Is the Best Month to Cruise the Caribbean?

The winter months are often considered to be the best months to travel the Caribbean because of the ideal weather. While winter is the peak season, the islands will have more open opportunities for visitors because of the high volume of travelers during this time. When planning your trip to the Caribbean, you can find the best restaurants and shops to explore during your stops at the islands. 

Winter can be ideal because the weather is less humid and rainy, so you can optimize your time outside for more time in the water and sun. Out of the winter months, January and February are more sometimes considered the best because they are less popular than December. Many people travel to the Caribbean in December to celebrate the winter holidays or because it aligns with their winter breaks. You can experience fewer crowds but still benefit from the peak season weather and attractions by going in January and February. 

Visiting during any month has advantages and disadvantages, so it ultimately depends on what type of weather and crowds you want. 

Is October a Good Time to Cruise the Caribbean?

Hurricane season in the Caribbean runs from June through November. During this time, August to October often has an increased risk of inclement weather. Because there is the potential for tropical storms, October may have fewer available cruise options. However, temperatures are still warm in many areas of the Caribbean throughout October, and the sun will likely shine most of the time. If you consider Caribbean cruises during hurricane season, stay flexible, as periodic rain showers are likely between times of sun.

Most cruise ships will do everything possible to avoid sailing through or near a hurricane or tropical storm. Your itinerary may change to avoid a storm, though many cruise lines will only cancel a trip if a storm makes it too difficult to cruise in or out of the home port.

Is November a Good Time to Cruise the Caribbean?

Is November a Good Time to Cruise the Caribbean?

Despite closing out the rainy season, November is an ideal month to take a Caribbean cruise. November cruises come before the busy winter season, so it’s typically less hectic with nice weather. With hurricane season dying down in November, you’ll likely experience great weather during the day. Additionally, you may still find good deals on your trip when booking a November cruise. 

The Regions of the Caribbean

The Caribbean can be separated into different regions, including the Eastern, Western and Southern Caribbean. When considering when to take your cruise, you should also consider which region or regions it’s sailing to. For example, some areas of the Caribbean are less affected by hurricane season, which may be more desirable for you. Cruises to each region differ regarding departure points, ports of call and the number of stops along the trip.


The Eastern Caribbean includes multiple islands within the British Virgin Islands like St. Maarten and St. Thomas, the Bahamas, Puerto Rico and Haiti. Most of these islands are close enough for cruise itineraries to include multiple stops within a few days, offering lots of variety. The comfortable temperatures are great for any activity, from snorkeling to lounging on the beach to exploring the islands on a hike. Cruises offer various excursions throughout the stops in this region, allowing you to get the full experience.

Eastern cruises typically include a day or two at sea when leaving from Florida ports, making this region ideal for travelers seeking more sightseeing. The Eastern region is also popular for shorter cruises and cruises leaving from more Northern ports, as the trip can be relatively short while still reaching several stops.

Many travelers prefer cruising to the Eastern Caribbean during the winter months, as many islands in this region stay warm and sunny throughout the winter without getting too hot and humid. On-shore excursions are also more comfortable during this time of year, which is ideal if you plan on exploring. Since hurricane season can heavily affect this region, cruising during winter is best to avoid tropical storms.


The Western Caribbean includes Mexican stops like Cozumel and Cancun, the Cayman Islands, Jamaica and Belize. Some Western cruises may also stop in the Bahamas. Cruises into this region typically depart from Florida ports, though cruises also commonly depart out of Gulf Coast states like Alabama and Texas. You’ll typically have a few different stops on Western cruises, with at least eight hours at each port. You can also expect a couple of full days at sea since the islands are more spread out in the Western region.

Western cruises are popular for travelers seeking outdoor adventure. Whether climbing waterfalls in Jamaica, jungle ziplining in Cozumel or exploring the Mayan ruins, Western cruise excursions offer numerous opportunities and exciting activities to make the most of your time on shore. This region is also popular among first-time cruisers, as these cruises offer a nice combination of on-shore and at-sea days.

The weather in the Western Caribbean is similar to that of the Eastern region. You’ll experience balmy conditions, perfect for outdoor excursions and relaxing in the sun. Because hurricane season also affects this area, the winter months are the best time to cruise to this region of the Caribbean. 



Numerous islands make up the Southern Caribbean, giving it the most variety of the three regions. Because this area is farther from any U.S. ports and there are so many potential islands to stop at, Southern Caribbean cruises are typically longer than cruises to the other regions. Many cruises to the Southern Caribbean will also make stops in the Eastern islands on their way through — the difference here is that where Eastern cruises turn around, Southern cruises continue on.

Southern cruises often stop at islands like St. Lucia, St. Kitts, Bonaire, Aruba, Curacao, Guadalupe and more. Depending on where your cruise departs from and stops, you may have a day or two at sea. Because there are so many more Southern Caribbean islands, these cruises are typically faster-paced, stopping at a new island every day of the cruise. Because of this factor, you should choose a Southern cruise if you’re really interested in exploring and sightseeing rather than relaxing. 

While any time of year can be enjoyable in the Caribbean, this is especially true of the Southern Caribbean. Many of these islands lie below the hurricane belt, meaning they’re less likely to be directly impacted. As such, there’s no season you’d want to avoid in this region, leaving the best time to cruise Southern Caribbean up to your preference. 

What Is the Best Time of Year to Go to the Caribbean?

Each season offers different advantages and disadvantages in the Caribbean. While there’s not necessarily a bad time to cruise to the Caribbean, the best time for you may depend on what certain seasons offer. Here is what each season is like in the Caribbean.


Spring months, like March and April, are part of the dry season, so they’re great times to cruise the Caribbean. Spring is a popular time for many people to go on a cruise, as they take advantage of spring breaks and perfect Caribbean weather. Many hometowns have yet to warm up by this time of year, making a vacation to the Caribbean the perfect way to warm up and start working on your summer tan. From the beaches to the tropical cuisine, a spring cruise to the Caribbean will get you in the perfect mood for summer. 

While spring is part of the Caribbean’s high season, it is one of the best times to visit because the weather is perfect. You have minimal risk of hurricanes and can avoid the rainy season, so you can optimize your time on the yacht deck admiring the view or exploring the various islands. 

Windstar Cruises offers several tours through the Caribbean during March and April, allowing you to explore your favorite islands or new destinations. With smaller ships, we can stop at smaller ports to bring you to hidden Caribbean gems and avoid the peak season crowds. 


The summer months are significantly less busy because it’s the start of the rainy season. Many people and families take their vacations in the summer because school is out, though Caribbean summer cruises may not be the best choice because of the potential for rain. While you may experience brief rain storms in the afternoons, the rest of the day can be nice and sunny.

If it’s not raining, expect the weather to be hot and humid, especially in late summer when the potential for tropical storms increases. If you stay flexible and pack appropriately, you can still enjoy a beautiful summer cruise with a little rain.



Fall is the peak of hurricane season, especially for the Eastern and Western regions. Despite fall having a higher risk of tropical storms, some islands are still worth sailing to during this time. Southern islands like Aruba, Curacao and Bonaire become popular cruising destinations during the fall because they’re outside the hurricane zone. Many islands also experience more comfortable temperatures in the fall.

Also, keep in mind that a higher storm risk doesn’t necessarily mean there’s a guarantee for a storm. And even if there is a storm, not every island will be affected. With this in mind, most cruise lines offer significant savings and deals on cruises during the fall season because fewer people want to sail. Early November can be a great time to explore the Caribbean through a late fall cruise. 


Many people cruise to the Caribbean during winter months to escape the cold weather. You can leave the ice and snow behind and replace it with endless beaches, scuba diving and vibrant sunsets over the ocean. 

Early December starts the peak travel season in the Caribbean. December is a popular cruise month because of the holidays, though January and February are typically a bit less crowded. January also begins the dry season, so there’s less chance of rain on the islands during the winter. The sun and warm temperatures make for a relaxing winter escape. 

Windstar Cruises tours the Caribbean throughout the winter, offering ample getaways and excursions for passengers. You can take a January trip to kick off the new year somewhere fresh and exciting or go in February for a romantic Valentine’s in a prime destination. 

Caribbean Cruises FAQ

If you’re interested in cruising or are planning your cruise, you likely have more questions. Doing your research to determine the best cruising time for you is the best way to decide when to book a Caribbean cruise. Here are the answers to a few more common questions about Caribbean cruises.

What Months Should I Avoid When Cruising to the Caribbean?

While there are advantages to cruising during each month, some months are just better to avoid. For example, many travelers like to avoid cruising from August to early November to avoid the worst of hurricane season. The summer is the Caribbean’s rainy season, which can take away from the experience of those who want to enjoy the sunny blue skies and the beautiful beaches.

When Are Cruises the Cheapest?

If you’re looking for the best deals, you need to know when to book your cruise. Booking last minute will typically be more expensive, so try to book as far in advance as possible. For example, if you can commit to cruise dates a year or more in advance, do it because rates will increase the closer you get to the trip. 

Additionally, avoid dates around major holidays, as demand is higher during these times and rates will reflect that. For example, consider the first week or two in January rather than booking a cruise between Christmas and New Year’s. Rates increase for the holidays and decrease again after they pass.

What Are the Greater and Lesser Antilles?

The Greater Antilles refers to the bigger islands in the Caribbean, including Puerto Rico, Jamaica, Cuba, the Cayman Islands and Hispaniola, which includes Haiti and the Dominican Republic. The Lesser Antilles refers to most of the smaller, Southern islands.

Are Bigger or Smaller Cruise Ships Better?

Depending on the cruise line you book a trip with, you may be sailing on a big commercial cruise ship or a small private yacht. While both options offer great opportunities for Caribbean cruises, a smaller cruise may be better for you if you’re looking for a more intimate trip. Large cruise ships can feel cramped with the number of people on board. Additionally, smaller ships can sail into smaller ports, allowing you to discover hidden gems in the Caribbean.

Cruise to the Caribbean With Windstar Cruises

At Windstar Cruises, we offer a more intimate and exclusive cruise experience from November to April. From finding small, private beaches to creating a pampered on-board atmosphere, we specialize in beyond-ordinary Caribbean experiences. Our ships carry less than 350 guests, so we can provide a more personalized trip for you. With this immersive approach to cruising, we’ll bring you closer to the cultures and destinations you visit. 

Explore our cruises to the Caribbean and book your trip today. 

Cruise to the Caribbean With Windstar Cruises

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