Caribbean - Eastern Cruise Guide and Reviews

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. 

Routes

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.