Best Time To Cruise To The Caribbean
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May

Cozumel
If you’re looking for decent weather but fewer crowds, one of the best months to cruise the Caribbean is May, the beginning of shoulder season, between the winter peak and the quieter summer months.
Depending on where you go, the weather is still near perfect, particularly in the Southern Caribbean islands, with lots of sunny days and balmy evenings perfect for a moonlit stroll on deck.

Cozumel
On Mexico’s east coast, where the island of Cozumel lies, May is hot, with temperatures in the 80s and over 11 hours of sunlight daily. Sunbathe on pristine white-sand beaches or get active with watersports like jet skiing and parasailing over the beautiful blue Caribbean Sea. The water clarity is excellent, too.
You could spot sea turtles laying their eggs on remote beaches—and on snorkeling expeditions, you may be lucky enough to see huge but harmless whale sharks. Prepare for an increase in humidity, though, as the month progresses.
June

St. Kitts
June is relatively quiet in the Caribbean; schools are not yet on vacation, and official hurricane season has begun. So it’s a matter of thinking about what you want from your Caribbean cruise when planning a June trip.
This can be a great month to visit Aruba, for example, if you’re into windsurfing and kite surfing; the winds are optimum in June for experienced surfers.
If you visit Cozumel in June, you’ll still find excellent water clarity for snorkeling. But do be aware that this is when a lot of seaweed is often washed up on the beaches.
The Southern Caribbean generally sees a lull in rainfall in June; both May and July receive more precipitation on islands such as St. Kitts and Nevis, Antigua, and the U.S. and British Virgin Islands. So head for this part of the region and you stand a good chance of plenty of dry, sunny days.
July

St. Lucia
Looking for an antidote to a too-crowded summer vacation? A summer cruise to the Caribbean may be just the ticket. July sees less crowded beaches and restaurants, and the whole region has a more relaxed vibe.
The Caribbean is one of the most fun places to go in the summer with your family since the kids are out of school. While the weather will be hot and humid during this time of the year, with some islands reaching 90 degrees on average, temperatures tend to cool down a little in the evenings, when they can hit a comfortable range within the low-70s.
Make sure to bring a rain jacket or poncho in case you get caught in some showers. Don’t forget the bug spray either, as high humidity and rain typically mean there are more mosquitoes, too.

Jamaica
In parts of the Caribbean, July is actually an anomaly in the rainy season, as many islands see a dip in precipitation between the much bigger rains of June and August. Jamaica, for example, sees 2.1 inches or 55mm of rain in July, compared to 2.5 inches or 65mm in June and 3.9 inches or 100mm in August.
July is also party time in some islands. St. Lucia celebrates its Carnival now, with two weeks of parades, dazzling costumes, and feasting.
August

Snorkeling in Bonaire
August is a great month to consider a cruise to the Southern Caribbean, which receives much less rainfall than the islands further north. Explore Fort Amsterdam, a UNESCO World Heritage Site, in Willemstad, Curaçao, then shop the vibrant open-air markets and sample the Dutch take on waffles. Snorkel or scuba on Bonaire, one of the world’s most celebrated and pristine diving spots.
While the weather is hot and humid elsewhere, the party spirit carries on; in fact, low season is a great time to travel to see locals at their most relaxed. August is usually when Barbados celebrates its Crop Over festival, marking the end of the sugar cane harvest. This is a joyous time to be on the island, with a week of parades, feasting, live bands, and lavish costumes.
If your travels take you to the British Virgin Islands in the first week of August, you’ll find the celebrations for the Emancipation Festival, remembering the islands’ emancipation from slavery, in full swing.
Read: Best Caribbean Islands to Visit in August
September

Curacao
Hurricane season takes off in September and lasts until early November. If you’re looking for a great special offer on a cruise, look for cruises during this time period.
The ABC Islands, Aruba, Bonaire, and Curacao, are popular destinations with cruise vacationers during the early fall, especially during the later part of hurricane season, since they’re outside of the Caribbean hurricane zone. Barbados, too, is a long way east and usually dodges the worst storms.

Bathsheba Beach, Barbados
If you don’t mind a little bit of unpredictability and tropical rain, the early fall season is also one of the best times to visit the rest of the Caribbean. Yes, it will be humid, but you can still spend your days splashing around in the sea and retreat to the air-conditioned cool of your ship in the evenings.
Come prepared with a waterproof jacket in case you do encounter some showers, and don’t forget to pack anti-nausea aids or medication to prevent seasickness in case the weather makes sailing choppier than usual.
October

Aruba
October, the later part of shoulder season, is one of the rainiest months in the Caribbean region and also the most likely time for hurricanes to sweep through. If you want to enjoy a cruise in October, the ABC Islands in the far south of the region are the best place to go.
While October is still one of the rainier months of the year here, actual precipitation is a fraction of what you’ll encounter further north. Aruba, for example, receives an average of 75mm of rainfall in October, but still enjoys eight hours of sunshine daily. The humidity is tempered by the trade winds, too.
Read: Warm Places to Visit in October
November

Cozumel
November sees the official end of hurricane season, with calmer weather being ushered in all over the region as the month progresses and the heavy rains ease off. This is still the low season, until Thanksgiving, after which everything starts to pick up again.
Late November and early December is the best time to cruise the Caribbean, East or West, for a dose of tropical sunshine before the Christmas crowds arrive.
The beginning of November is a great time to visit Mexico for a unique cultural experience. November 1 and 2 brings the Day of the Dead festivities, when the deceased are honored with candlelit vigils, parades, and family picnics in graveyards.
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