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Aruba is outside of the hurricane belt and doesn’t have a monsoon season. 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.
What Is the Best Time of Year to Go to the Caribbean?
Of course, peak season cruising means higher prices and a winter cruise will cost you more on average than a summer or fall cruise. The cheapest time for a Caribbean cruise is between August and November because school is back in session and the threat of hurricanes and a higher chance of rain. 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.
When is the Caribbean’s dry season?
The weather is not the only factor as to why these sailings are cheaper-- since most American schools are back in session, the demand for cruising decreases compared to the peak in June and July. Here is a look at what to consider when deciding the ideal month for your cruise vacation. Crop Over is a summer festival in Barbados that celebrates the end of the sugar cane harvest. During July and into early August, expect special markets, parades and celebrations.
Eastern Caribbean

Best of all, families can embark on unforgettable journeys together – like ziplining through lush canopies or exploring underwater World War II shipwrecks. Kids will bring home more than just souvenirs, but also lifelong memories of time spent with loved ones. To get the best price on a cruise, it’s generally recommended to book several months to a year in advance. This early booking period allows you to take advantage of early bird discounts and a wider selection of cabins.
Best Time for a Caribbean Cruise
If you’re cruising to ports like Aruba or Bonaire in the Southern Caribbean, you’ll likely experience the warmest conditions, as they’re the closest to the equator. Take advantage of the unique winter climates by jet skiing along one of Aruba’s pristine beaches or strolling through the lush botanical gardens in Martinique. 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. During these mid to late summer months, the Caribbean is also at the greatest risk of experiencing tropical storms, multi-day rainfalls, and even hurricanes.
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The islands are less crowded too, allowing for a more relaxed and intimate experience. Despite this, the showers are usually short-lived and often occur in the afternoon, making it still possible to enjoy most of the day outdoors. This period also coincides with the hurricane season, with the highest risk of hurricanes from August to October.
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.
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. 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.
From casual poolside bites to Pan-Asian flavors at Tamarind and fine dining at Pinnacle Grill, our menus offer a culinary adventure. However, keep in mind that some Southern Caribbean cruise destinations, such as Bonaire, Aruba and Barbados are rarely threatened by hurricanes as these islands are closer to the equator. While it’s mostly true, there are some modest variations in temperature from month to month. Air and water temperatures are noticeably cooler in the northern climates during the winter, which makes a Bahamas cruise less appealing from December through February.
As such, top attractions and activities could mean wildly different things to different people." Ships are filled with stylish, adult-oriented bars promising a hopping scene late into the night as well as hipster venues like a colorful karaoke lounge. Onboard entertainment is inventive and often edgier than what you might see on traditional-style cruises. However, if an upscale cruise experience is what you seek, Windstar Cruises can deliver. The line's seven-night Classic Caribbean itinerary aboard Wind Surf should be on your radar. The bottom line is that the best Caribbean cruise for you depends a lot on your travel style.
However, this also corresponds to the driest season, which is great for outdoor activities. The late summer and fall can reach into the 90s with high humidity and a greater chance of rain. 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. "Perfect weather" in the Caribbean would likely equate to sunny days with warm water, delightful breezes, and minimal rainfall and humidity. For that kind of weather, Brittney Magner, vice president of luxury travel sales at Royal Travel and a Travel + Leisure A-List Advisor, says January through May is the ideal time to visit.
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While the Southern Caribbean maintains its sunny disposition, other destinations welcome refreshing ocean breezes. Occasional light showers are the perfect excuse to head inside and tour the Graycliff Chocolatier, where you can create your own decadent masterpiece with local ingredients like mango and lime. Or sip on an aromatic flight of wines at Bahama Barrels while hearing stories from locals. Then, cruise into clearer conditions and partake in one of the many music festivals that dot the rural roads like the Pure Grenada Music Festival in May or the St. Kitts Music Festival in June. Whether swimming in the crystalline ocean or singing in the refreshing rain, come prepared with a light rain jacket, loose clothing and a heart full of wonder.
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. A good portion of Magner’s clients are visiting the Caribbean for boat charters. "For example, if you go to Anguilla, you can take a boat over to St. Barts. Or you can experience all the little islands around the Dominican Republic or Turks and Caicos."
"Essentially from the time that all the New Year's Eve confetti is swept up until President's [Day]." On the Southern Caribbean Seafarer cruise, couples can visit Curacao, Aruba and Half Moon Cay, the line's private island in the Bahamas. An overnight stay in Curacao allows cruisers to dive deeper into the island's history, culture and natural lures. Aruba offers diversions below and above the water, from submarine tours and snorkeling to hikes and four-wheeling adventures. The stop at pristine Half Moon Cay provides an easy and relaxing beach day.
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