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Ultimate Guide to the Caribbean Cruise Season

Decades ago, the Caribbean cruise season was much shorter than it is today. Ships really only plied the Caribbean Sea during “high” season—the prime months between December and March—when the seas are calm and the weather temperate. Now, the Caribbean has become a favored cruise destination with lines like Royal Caribbean, Carnival, and Disney staying in the region all year round. Our Caribbean Cruise Guide will have you carousing on the high seas no matter the time of year.


When to Go?

Hurricane season technically runs from June 1 through November 30, but the chance of running into poor weather is actually fairly small. If you do decide to book a voyage during hurricane season, do yourself a favor and purchase trip insurance that includes provisions for hurricanes.

“Shoulder” seasons are also good times to cruise the Caribbean. Ships reposition to and from the Mediterranean to the Caribbean during these shoulder months of September and October and April and May. Excellent deals can be had during these time periods.

Where to Go?

You will be overwhelmed with choices when you start looking for “the perfect” Caribbean cruise vacation. You’ll see itineraries labeled as Eastern Caribbean, Southern Caribbean, and Western Caribbean. Each region has its unique charms. Here’s a look at three regions.

Eastern Caribbean

Eastern Caribbean cruises highlight the ports of the Bahamas; Hispaniola, which encompasses the Dominican Republic and Haiti; the U.S. Virgin Islands of St. Thomas, St. John, and St. Croix; the British Virgin Islands of Tortola, Jost Van Dyke, and Virgin Gorda; the Turks and Caicos; Puerto Rico; and St. Maarten/St. Martin.

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Not–to–Be Missed Port: Nassau, New Providence Island

The capital city of the Bahamas is a popular cruise port and one that is usually very crowded. Visitors to Nassau enjoy beautiful sandy beaches as well as a range of hotels and casinos. There is even a bridge connecting New Providence to Paradise Island—home to the popular Atlantis Resort complex. Duty-free shopping along Bay Street is a major pastime here and the Straw Market is equally popular. Cruise ships dock at Prince George Wharf and the port facility includes Festival Place, which is staffed by the department of tourism so you can pick up maps and ask questions before heading out for the day. Tourism companies are also on location to help you book boat trips, land tours, and basic taxi services.

Southern Carribean

Itineraries that focus on the Southern Caribbean call on the beautiful islands of Antigua, Barbados, Bequia, Curacao, Dominica, Guadeloupe, Martinque, St. Lucia, Aruba, Bonaire, Grenada, Nevis, St. Barthelemy, St. Kitts, St. Vincent, and Trinidad. Puerto Rico’s San Juan is also often a stop on a South Caribbean voyage.

Not–to–Be Missed Port: St. Barthelemy

This yachter’s paradise is a sophisticated vacation haven for the rich. While the rocky island of St. Barths is relatively small (it covers eight square miles), you’ll find gorgeous beaches, lots of high-end retail shops, and restaurants serving the best French food outside of Paris. The two main areas to visit are Gustavia (where most ship tenders drop passengers) or St. Jean. Beach lovers usually head to Gouverneur Beach, St. Jean, or Anse des Cayes.

Western Carribean

Travelers who prefer Grand Cayman and Mexico often select a Western Caribbean cruise. This region includes Belize, Jamaica, Roatan, Grand Cayman, Labadee and Mexican ports like Costa Maya, Playa del Carmen, Cancun, and Cozumel.

Not–to–Be Missed Port: Grand Cayman

If you love white sand beaches that are powdery soft, snorkeling, and scuba diving, then Grand Cayman is for you. Opportunities for serious lounging abound at Seven Mile Beach on the west side. At Stingray City to the north you can interact with a group of Southern Stingrays. This spectacular island is always worth a visit. Be aware, however, that it’s a port that is often skipped during inclement weather since tendering here can be dangerous. If the weather is good, however, you won’t encounter any problems. While most ships bring their guests to the island of Grand Cayman, you may be able to arrange a shore excursion to one of the out islands like Little Cayman or Cayman Brac.

Who Sails the Caribbean?

It’s safe to say that almost every cruise line sails the Caribbean at some point throughout the year. Lines with a major presence in the region include Carnival, Celebrity Cruises, Disney Cruise Line, Holland America, Norwegian Cruise Line, Paul Gauguin Cruises, Princess Cruises, Royal Caribbean, SeaDream Yacht Club, Star Clippers, and Windstar Cruises.

Photo credit: Photos courtesy of Royal Caribbean

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