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We have the answers so your first time will be nothing but smooth sailing. Temperatures can be warm and enjoyable, but many people find that the humidity can be unpleasant. Rain is also more frequent, which can make excursions and exploring ports of call far less enjoyable. Rainfall is rare in January, and when it does occur, it is likely to clear up fast. January is the coldest month in North America and Europe, so you can expect a lot of tourists to come at this time. The warm, clear, and calm waters of the Caribbean are a significant part of the appeal of cruising south.
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For cruisers wanting to explore the local culture through culinary tours or sampling the region’s famous rum products, there are a variety of cultural events throughout the year. Summer can be a great time to enjoy these types of excursions with fewer crowds. However, do note if you are doing a DIY activity that some businesses close during September, the low season. Budget, crowds, weather and activities can all play a role in deciding the optimal time to set sail. Weather is drier and warm in December, making the early part of the month a great relaxing getaway.

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With year-round opportunities to sail through the teal-blue waters, any of our Caribbean cruises can transport you to a state of total relaxation and bliss. 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.
Cultural Events and Holidays
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. 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. The weather on excursions and beach days will be more comfortable in the winter months. Whether you’re walking around Mayan ruins in Costa Maya, lounging in a beach chair in St. Thomas, or going hiking in St. Lucia, you won’t feel as hot as you would in the peak of summer.
Overview of Caribbean cruises
Let’s take a closer look at everything you need to know to book your Caribbean cruise at the time that’s best for you. Trinidad claims the title of the hottest location, with an average high of 91°F (33°C), whereas the Bahamas offers a cooler climate with an average high of 82°F (27°C). 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. While there isn’t a particular time of year that needs to be avoided when cruising to the Caribbean, you may prefer a certain time of the year based on your schedule and cruising style.
The cheapest time for Caribbean cruises runs from late summer into fall, when hurricane season is at its peak. If this is the only chance you have to cruise, keep in mind that itineraries can change or be canceled depending on the weather. 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. 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.
Whether you wish to float down transparent rivers on a bamboo raft or zipline through lush rainforest canopies, the wonders of the Caribbean are ready for your arrival. As the name suggests, precipitation increases throughout the wet season, but showers are brief and sporadic during the first few months. The risk of rain is relatively low at this time of the year, though you might experience the occasional shower.

Keep in mind that July and August means families are taking advantage of school breaks and vacation days. If you're looking for a more low-key Caribbean cruise this time of year, look to the smaller islands of the region. July and August can be the most expensive months to cruise the Caribbean, but there are plenty of exceptions.
What is the best month to cruise the Caribbean?
During July and into early August, expect special markets, parades and celebrations. In Grenada, Spicemas, held during the second Monday and Tuesday in August, celebrates the island's multicultural heritage with live music and festivities. July brings rain to the Eastern Caribbean (including Puerto Rico and the Virgin Islands) and August is wet in the Bahamas, Martinique and Dominica. Caribbean Sea temperatures are at their warmest in August, reaching 83 degrees on average. Caribbean cruises in January and February can be extremely budget friendly, with sailings available from $50 per person, per night.
5 Best Adults-Only Caribbean Cruises Fun Times For Grownups - TravelAwaits
5 Best Adults-Only Caribbean Cruises Fun Times For Grownups.
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That said, temperatures tend to be much higher during these months reaching up into the 90s (30s Celsius). If I were to narrow it down even further, I'd say the best time to cruise to the Caribbean is early December. It's a fun way to create a break between Thanksgiving and the December holidays. If it's the latter, that's when you get last-minute deals on cruise ships with unsold cabins. However, even if that last-minute cruise is cheap, the 11th-hour airfare or pre-cruise hotel booking could eat into your savings.
From Bacchanal in Jamaica to Carnival in the Cayman Islands, the sounds of rhythmic drums waltz through the island streets. At the Batabano Festival, taste local delicacies including macaroni pie, fresh-caught seafood and flaky pastries filled with tender meat. For a November getaway, consider Curaçao and Jamaica, both of which typically receive less than 4 inches of rain, making them ideal destinations.
Kids will bring home more than just souvenirs, but also lifelong memories of time spent with loved ones. In other words, plenty of cruise lines offer Caribbean voyages during this period, but demand is lower than during the peak travel months. This increases the chances of scoring an amazing Caribbean cruise deal.
When planning your trip to the Caribbean, you can find the best restaurants and shops to explore during your stops at the islands. While the rainy season lasts from the beginning of October through November, these are some of the best months to cruise to the Caribbean. Sip and savor your way through the Barbados Food and Rum Festival in October where local chefs prepare culinary treasures that give you a taste of island life. In the Grand Cayman, don your tricorn hat and line the streets to watch pirates invade George Town during Pirates Week Festival.
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