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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. Once you reach July, you are at the very peak of the Caribbean’s wet season, which means you can expect high temperatures, plenty of rain, and humidity levels that can be uncomfortable.
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Cruise lines do an excellent job of monitoring tropical storm development and plan well ahead. Most Caribbean cruises in March and April run close to $100 per person, per night. Spring break is a popular time to cruise and fares can fluctuate during that time. January and February are two of the best months to cruise the Caribbean for those who need a break from gray, wet winter weather. You'll also find the some of the most diverse cruise lengths and itineraries throughout the region in January and February.
The Best Time to Cruise the Caribbean
Foodies in particular will find that each island has its own unique flavors (and loves to celebrate them). St. Kitts and Nevis, for example, holds its Restaurant Week in mid-July. It's a week-long celebration of local cuisine challenges, inviting chefs to create dishes featuring one key homegrown ingredient.
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Expect to see flamingos, coral reefs, tropical fish, hummingbirds, egrets and turtles this time of year. This month falls just outside the peak tourist season and before the start of the hurricane season, offering a sweet spot with less crowded beaches, affordable prices, and generally pleasant weather. With the rainy season not yet in full swing, visitors can enjoy warm, sunny days perfect for exploring the islands’ natural beauty and sunswept beaches. 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.
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A few years ago, I cruised the Western Caribbean near the end of October and it poured the whole time. That's where I learned the meaning of the word "torrential." Even with all that rain, it wasn't a bad cruise. Book an early shoulder season cruise in May to take advantage of the best weather with fewer crowds. Explore Fort Amsterdam, a UNESCO World Heritage Site, in Willemstad, Curacao, then shop the vibrant open-air markets and sample the Dutch take on waffles.
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The shoulder season sits between the peak travel times and the off-peak periods, offering a sweet spot for travelers looking for value without sacrificing a pleasant travel experience. During this period, the Atlantic hurricane season makes it less desirable for most travelers, leading cruise lines to offer significant discounts. If you’re looking for a budget-friendly cruise and are prepared for bad weather and itinerary changes, the off-peak season can be a great time to cruise.
Taking a Cruise in December
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During the back end of the dry season, meaning January until the end of April, average temperatures rise by a few degrees, but the skies usually remain clear. For a November getaway, consider Curaçao and Jamaica, both of which typically receive less than 4 inches of rain, making them ideal destinations. The weather in the Caribbean is still warm during October, reaching average highs in the mid to upper 80s. July is the perfect month for snorkeling as the ocean remains pleasantly warm, with an average temperature of 83°F (28°C).
Tons of music and jazz festivals take place around the Caribbean this time of year, including the Pure Grenada Music Festival in May and the St. Kitts Music Festival in June. If your Caribbean cruise takes place over Easter, Virgin Gorda (part of the British Virgin Islands) holds a weekend filled with parties and calypso music. In Jamaica, parades known as Bacchanal, take to the streets during both months. Here's how the entire year stacks up so you can identify the best time for your travel party to cruise the Caribbean. Go biking around Duval Street in Key West with a stop for a refreshing key lime pie ice cream cone. Watch the sunset from your ship after a day of hanging in a hammock on a Cozumel beach.
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. If it’s not raining, expect the weather to be hot and humid, especially in late summer when the potential for tropical storms increases.
For the super adventurous cruisers who want to swim with sharks, there are plenty of excursions, especially in the Bahamas. While temperatures rise in many places across the U.S. during the height of summer, July and August temperatures in the Caribbean are in the upper 70s and 80s. Beginning at the very end of April and into May, Antigua Sailing Week is globally known for its prestigious sailing races and parties.
The best time to cruise the Western and Southern Caribbean is winter, as the waters are warm, and the temps are comfortable. Spring is a great time to take an Eastern Caribbean cruise as the cooler waters near the Bahamas heat up. To avoid the busy season, the best time to go on a Caribbean cruise is from November to early December.
You'll have options like splash zones for the little ones, monster slides for the adventurers and kids clubs for all ages. There's never a bad time to cruise to this giant blue fishbowl with a bazillion beaches to explore. This may be the perfect season for you if you prefer not only less crowded Caribbean islands, but possibly a less crowded onboard cruise experience as well.
Some islands may experience cooler temperatures but it is rarely ever below 60˚F (15˚C). These balmy conditions offer excellent swimming and snorkeling as well as warm evenings perfect for exploring local cuisine or simply relaxing after a long day at sea. Another factor to consider during this time is that most schools are in session so there will be fewer children onboard resulting in an overall quieter environment.
Plus, winter storms in the U.S. can increase wave action in the Atlantic and in the Gulf of Mexico. The farther north your departure port, the more likely you are to experience a rough ride until your ship sails south into calmer water. A great way to dive deeper into the cultures of the Caribbean islands you visit is by experiencing local holidays and festivals. Festivals happen throughout the year and can be a unique way to experience a port during your cruise.
While it is possible to enjoy a pleasant cruising experience in the Caribbean throughout the year, it is generally understood that cruising during a summer month is the riskiest. The Caribbean Sea is usually relatively calm during late fall and early spring. As you can imagine, this helps ensure all passengers enjoy a smoother, more relaxing cruising experience. April is the perfect month for swimming and water activities in the Caribbean, where the average ocean temperature reaches a warm 27°C (80°F).
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