Caribbean - Eastern Cruise Guide

maho bay st. martin
Maho Bay, St. Martin - by SIME/eStockPhoto

Why go?

The Caribbean is all about beaches, and it’s where you’ll find the most coveted strands of sand in the world. The classic image of the region — blue skies, clear water, and palm-fringed beaches — is synonymous with the ideal vacation for many sun-worshipping Americans.


In the Eastern Caribbean, you’ll find those things in ports bustling with thousands of other cruisers, sometimes more than 10,000 at a time. (In comparison, the Southern Caribbean, for example, is full of smaller, quieter spots.) In addition, convenience is a key factor for many cruisers when they choose the Eastern Caribbean route — most cruises depart from Florida and are easily accessible by air from all over the country.


If you count every sandbar, there are thousands of islands in the Caribbean Sea, but just 40 make it onto most maps. About a dozen are included on cruises to the Eastern Caribbean; the rest fall into the Western or Southern Caribbean regions. Weeklong itineraries include some combination of the U.S. Virgin Islands (particularly St. Thomas), St. Martin (French and Dutch sides), British Virgin Islands (Virgin Gorda, Jost Van Dyke, and Tortola), Puerto Rico, and Antiqua, plus the Bahamas.


While technically outside the Caribbean basin, visits to Nassau, Grand Turk, and the cruise lines’ private Bahamian beaches are part of many Eastern Caribbean routes. Key West, on the southernmost tip of Florida, is also a frequent port. Some ships — mostly the smaller ones — visit tiny islands like St. Barts, Anguilla, and Les Saintes, places where jet-setters and celebrities the likes of Jay-Z, Beyonce, and Jennifer Aniston go to get away from it all and hide from the paparazzi in private villas and chic boutique hotels.


Besides sunbathing, snorkeling is a top pastime on Eastern Caribbean cruises, and one of the best spots is in gorgeous St. John, a small island comprised mostly of U.S. National Park land. Although ships don’t call there, you can easily take a ferry from St. Thomas and enjoy the gorgeous crescents of white sand and the marked snorkeling trails offshore at Trunk Bay. Snorkeling is also good at Cinnamon Bay and Maho Bay. History buffs will appreciate the grand 16th-century El Morro fortress in San Juan, Puerto Rico, and for shoppers, St. Thomas and St. Martin (French and Dutch sides) are full of jewelry and souvenir stores.

When to go

The Caribbean cruise season, including the islands of the eastern region, runs year-round, with the greatest number of ships there between October and April — when vessels that spend summers in Europe or Alaska move to the Caribbean for the winter. The high season is January through April, as well as holiday weeks like Thanksgiving, Christmas, New Year, and Easter, when people are eager to escape the winter weather up north to bask in the sun-drenched islands down south. Temperatures are warm and toasty all year, ranging from the mid 70s to the high 80s Fahrenheit. June tends to be the rainiest month, but it rarely rains for an entire day.


Hurricane season in the Caribbean is June 1 through November 30, with the peak months for hurricane activity being September and October. Still, chances are you won’t encounter a drop of rain or a single whitecap. The beauty of traveling by sea is that ships can change course to avoid storms.


If you want to save some money and are OK with the risk of cruising during the hurricane season, then September through early December — before the Christmas rush — are the months to find a deal. You’ll also encounter fewer crowds and fewer families with kids. 


The average Eastern Caribbean cruise is seven nights long, and most ships sail round trip year-round. The vast majority depart from Florida (Miami, Fort Lauderdale, or Cape Canaveral), though there are also a few sailings out of Puerto Rico and St. Thomas, as well as ports along the East Coast, including New York, New Jersey, Baltimore, Norfolk (Virginia), and Charleston (South Carolina).


Here are two of the most common itineraries, divided by the big ships — which require significant infrastructure in ports — to small ones that can call on much smaller and less-developed islands:

How to Get There

Big Ships:

The seven-night route begins and ends in Florida most of the time and visits three or four ports: Nassau (Bahamas), Grand Turk, and/or a cruise line private island in the Bahamas (such as Disney Cruise Line’s Castaway Cay or Holland America Line’s Half Moon Cay), plus St. Thomas, St. Martin, and Puerto Rico.

Good For: These bustling ports offer beaches and shopping, especially souvenir shops and duty-free jewelry from international chain stores. Cruise line private islands are big on water sports and kids’ activities. In each port, you’ll also find plenty of active excursions sold by the cruise lines, including everything from ziplining to biking, diving, and snorkeling — often with either stingrays or dolphins. Day cruises, which offer snorkeling or partying on boats or catamarans, are popular too.

Downside: This one is easy: Crowding. There can be more than 10,000 cruise passengers in town at the same time in any of these three ports, so traffic jams are common, and quiet local charm can be hard to find.


Small Ships:
These seven-night routes begin and end in St. Thomas, San Juan, or St. Martin, and sometimes Fort Lauderdale, and visit five or six ports (one a day usually): several British Virgin Islands, St. John, St. Barts, Anguilla, Les Saintes, and/or Dominica.

Good For: These are great choices for beach lovers and privacy seekers. The white sand in these destinations is soft and dreamy, with plenty of romantic coves.

Downside: It might take you an extra flight to get to the port of embarkation, since many of these cruises depart from a Caribbean island.

Cruise Lines That Sail Caribbean - Eastern

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