The Caribbean is one of the most popular year-round cruising destinations and for good reason! You're promised breathtaking beaches, delicious cuisine, and fun excursions no matter what region you sail to.
Thankfully, Caribbean cruises are a wonderful vacation for the majority of the year. If, however, you're seeking ideal travel conditions, some times of the year should be avoided, as you do not want to be disappointed once your vacation has started.
Overall, there are two main times of the year in the Caribbean: the wet and dry season. The region is subject to far more rainfall during the wet season, which runs from the beginning of May through October.
Additionally, the wet season has higher average temperatures, so if you are sensitive to the heat, you are better off cruising during the dry season, which is from November through April.
Read more: Eastern vs. Western Caribbean Cruises
The worst months to cruise to the Caribbean are July, August, and September
As mentioned above, the Caribbean's wet season runs from the beginning of May through October. It is no coincidence that the Atlantic hurricane season falls within this timeframe.
While your safety is not at risk if you choose to cruise during hurricane season, the chance of a storm impacting your voyage increases during these months. Thankfully, the peak of activity is during August, September, and October, with 96% of major hurricanes forming during these months. That, however, doesn't mean that July won't see the occasional storm.
In addition to potentially disruptive weather that could alter your itinerary, the summer months are the hottest in the Caribbean. It's not uncommon to see temperatures in the high 90s, coupled with high humidity, during July, August, and September.
During the 2023 hurricane season, Tropical Storm Idalia disrupted numerous itineraries, such as Disney Cruise Line's Disney Fantasy.
Rather than cruise to the Western Caribbean (i.e., Cozumel, Mexico; Falmouth, Jamaica; and Grand Cayman), the ship visited the Eastern Caribbean islands of Tortola and St. Thomas. Similarly, Wonder of the Seas skipped a scheduled visit to Roatán, Honduras, spending another day at sea. Just a few weeks later, Hurricane Lee did the same.
Thankfully, cruise ships are equipped with numerous different activities and events to keep cruise ship passengers occupied, so if your sailing ends up canceling a port of call, rest assured knowing that there will be plenty for you to do onboard, even if the weather isn't ideal for sunbathing by the pool.
Even though cruise lines will always do their best to make sure that you're able to board your ship, even if you sail to a different destination, there's always a chance that it could be outright canceled if conditions are too harsh.
Plus, ships that sail around storms could still potentially sail through rough seas or encounter cloudy days that dampen your plans to spend all day on the lido deck. If you are subject to motion sickness, you probably won't want to spend your entire cruise feeling ill due to the rocking of the ship.
Fewer ships sail to the Caribbean during the wet season, too. The majority of cruise lines increase their deployment to the region during the dry season, so you'll find far more ships and itineraries during the winter, such as in November, December, and January. This will give you more options when it comes to flexibility, as there will be more ships in operation each week.
Some of the cheapest months to book a cruise to the Caribbean coincide with the worst months to cruise to the Caribbean
Since the majority of American children return to school sometime in August, you'll usually see fares for cruises to the Caribbean begin to decrease around that time, as demand is not as high as during the peak summer months.
A 7-night cruise onboard Carnival Celebration departing on July 20, 2025 starts at $879, while the same itinerary departing in August starts around $580 per person.
This is a huge price difference! If traveling with just one other person, you would save close to $600 on the cruise fare alone by sailing during hurricane season. You could put that towards cruise add-ons, such as drink and Wi-Fi packages, shore excursions, and more.
Even if your cruise ship is fully sold out, the islands will likely not be as crowded as during the peak months of June, July, and early August, as the demand for tourism, in general, tends to decrease when school starts back up.
Whether you want to save money or encounter fewer crowds, there are definitely advantages to cruising during the "worst" months to the Caribbean.
Read more: What is the cheapest month to go on a cruise?
The best months to cruise to the Caribbean are January and May
Following the busy holiday season, prices in January for Caribbean cruises decrease. While the Bahamas is subject to the occasional cold front, those sailing further south to the Caribbean are likely to find warm, but not unbearable, temperatures throughout the entire month. The average high in Mexico in January, for instance, is around 80 degrees! Similarly, the average high in St. Maarten in January is 83 degrees.
While only January is technically in the Caribbean's dry season, May does not see as much rainfall as other months, namely those in the latter half of the wet season.
The only downside is that these months don't align with the majority of American school schedules. Plus, you might not want to use PTO in January right after the holidays when you have an entire year ahead; you might not be able to if you had to take some time to visit with family, either! This just goes to show how many considerations there are when planning a cruise.
Read more: What is the best month to cruise to the Caribbean?
Regardless of when you book your Caribbean cruise, it is important that you purchase travel insurance
When dreaming about your perfect tropical getaway, visions of things going wrong will likely stay repressed in the back of your brain. Why would you want to imagine getting injured or having your cruise canceled altogether? Unfortunately, these things do happen, and while we might not want to think about them, we must be always prepared.
Travel insurance ensures that you're protected if things do not go as planned. It's meant to provide peace of mind to travelers in the event that something does go astray while on vacation. Usually, the price is around 6-15% of the total cruise fare.
Each cruise line has its own version of travel insurance that guests can purchase at the time of booking. While the exact coverage varies, you can expect to have things like travel delays, medical emergencies, and luggage mishaps covered. Additionally, you'll usually receive 24/7 access to a dedicated travel hotline.
Read more: Cruise travel insurance and why you need it
Elizabeth Wright
Elizabeth graduated from New York University's Arthur L. Carter Journalism Institute with her M.A. in Journalism in May 2023. Growing up, she had the privilege of traveling frequently with her family and fell in love with cruising after sailing on the Oasis of the Seas her freshman year of high school. She wanted to pursue a career that highlighted her passion for travel and strengths as a writer.
