Caribbean Cruise Travel, Vacation and Holiday Guide

Guide to Cruise Ships, Cruising, and Cruise Ports in the Caribbean

© Disney Cruise Line

The Caribbean is one of the world's most popular cruise destinations, but not all Caribbean cruises are created equal. Get onboard with my Caribbean Cruise Guide to plan a cruise that best fits your budget, interests, and schedule.

Choosing a Caribbean Cruise Line

About 20 cruise lines currently sail the Caribbean. Most Americans choose big-ship cruises such as those offered by Royal Caribbean and Carnival; these ships offer tons of amenities and activities but are limited by size to only the largest ports. Smaller ships operated by the likes of Windstar can get into smaller, less-traveled harbors. Bargain-hunters gravitate toward the big ships; lines like Seaborn and Cunard provide a luxury experience.

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What Caribbean Cruise Itinerary Should I Book?

Not every Caribbean island has a cruise port, but the list is growing and cruise ships are stopping in more exotic locations. Most cruise lines offer Western and Eastern Caribbean itineraries, so that's often the first choice you'll need to make. If you go with the big ships, you'll typically see ports like San Juan and Grand Cayman; smaller ships will get you into places like Virgin Gorda, BVI, and Nevis. Lines like Royal Caribbean and Disney Cruise Line offers stops at private islands.


How Long Should I Cruise the Caribbean?

Most Caribbean cruises are either 3, 4, 7 or 10 nights. Longer cruises often combine Caribbean port calls with stops in Mexico's Riviera Maya, Central or South America, including Panama Canal transits. Longer repositioning cruises can begin or end in the Caribbean as lines move ships to Europe seasonally. Price is one factor in how long you cruise; another is how long you enjoy being at sea. Even a big ship can feel confined after a few days; choosing itineraries with more, longer port calls can help.


When Should I Cruise the Caribbean?

Cruise lines ply the waters of the Caribbean year-round; winter is the most popular season, and when you have the most of ships to choose from. Summer is the time for bargain-hunting and cruises to Bermuda. Spring and fall are when cruise lines reposition ships between the Caribbean and Europe, offering longer transatlantic trips. Fall is hurricane season in the Caribbean, but cruise ships – unlike islands – can be rerouted to avoid most storms.


Which Caribbean Shore Excursions Should I Book?

You can see a Caribbean cruise port on your own or with a shore excursion booked with your cruise line. Some ports, like Nassau and Southampton, Bermuda, offer easy access to town; others are remote and require ground transport. Group outings are easier to arrange but often more expensive and crowded; planning your own excursion is more rewarding if you want to get away from the touristy areas and experience real island culture.

What Should I Pack for a Caribbean Cruise?

There's two factors to consider when packing: cruising and Caribbean. Both require you to bring travel documents like your passport. For cruising, you may want to bring a tux or evening gown for the traditional Captain's dinner, for example, while you'll need sunscreen and bug spray for the on-island portion of your trip. I also recommend bringing a backpack for carrying belongings on shore excursions, with a waterproof bag so you can change out of wet clothes before reboarding.


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