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What is the best month to cruise the Eastern Caribbean?

What is the best time of year to go to the Caribbean? December through April is the peak season for Caribbean cruising. During this time, you'll experience the best weather and some of the most entertaining holidays and festivals.



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Caribbean Seasons
Rain is more frequent in the wet season, but the temperatures are warmer. Wet season and dry season are both good times to cruise the Caribbean. The worst time for a Caribbean cruise weather-wise is August to September, as it is peak hurricane season.

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The best time for a Caribbean cruise is from December to April when the weather is dry, sunny, and clear skies on most days. The ideal cruising conditions of mild temperatures and calm waters typically last throughout winter and spring, making it the prime Caribbean sailing season and very traveler-friendly.

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According to the U.S. National Weather Service (NWS), hurricane season in the Caribbean runs from June 1 through November 30 and normally peaks in August and September.

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September is the cheapest time to book a Caribbean holiday as it falls in the middle of hurricane season. However, don't let that put you off, as this usually just means there's a greater chance of showers at that time. Hurricane season in the Caribbean runs from June 1 to November 30.

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If you'd rather see the sunrise while sailing south or east, staying on the port side is your ideal choice as well. Choose the starboard side for the opposite situation: sunsets are visible on southbound and eastbound sailings while sunrises are visible on northbound and westbound cruises.

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Haiti, Trinidad and Tobago, Puerto Rico are all considered least safe Caribbean Islands to visit.

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Eastbound cruises get the most sun on the port side; westbound on the starboard side. Watching a sunset over the ocean or seeing the sun slip behind distant islands can also be a reason for a side preference. To catch sunsets, you'll want to be on the port side on northbound cruises and starboard on southbound cruises.

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When is hurricane season in the Caribbean? According to the U.S. National Weather Service (NWS), hurricane season in the Caribbean runs from June 1 through November 30 and normally peaks in August and September.

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To avoid crowds and experience cooler temperatures, consider traveling in the shoulder months of May and September or early October. Most Mediterranean cruises sail in the summer months, when the sun and sand in coastal ports are at their peak and cities come alive with activity.

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The safest Caribbean islands to visit
  • Barbados.
  • The Dominican Republic.
  • Anguilla.
  • St. Maarten/St. Martin.
  • St. Barts.
  • The Virgin Islands.
  • Antigua.
  • Turks & Caicos.


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Midship staterooms on the lowest passenger deck are the most excellent spot to be on a cruise ship in this instance because you don't feel the vessel sway as much.

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Fly mid-week In most cases, the cheapest day to travel to the Caribbean is a Tuesday and the cheapest day to return is a Wednesday.

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The best time to visit the Caribbean is during its driest months, from February to May. But the Caribbean islands enjoy a hot, tropical climate all year round, with average highs of 82°F. The wettest period is between July and November, although the official hurricane season lasts from June to November.

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