Caribbean Cruise Guide

caribbean cruise destinations dominican republic beach
Beach in the Dominican Republic - by Thinkstock

Why go?

Photo by the Aruba Tourism Authority

The Caribbean conjures up thoughts of bright turquoise water, white-sand beaches, swaying palm trees, and warm, sunny weather. The best part: It delivers.

Caribbean cruise itineraries are broken up into three routes: eastern, western, and southern. Your vacation length, ideal embarkation port, and interests will determine which is best for you.

For example, the eastern route offers beautiful beaches and lots of water sports. You can zipline through 200-year-old mango trees in St. Martin, find peace and quiet at Virgin Islands National Park in St. John, or hike among the waterfalls and wildflowers in El Yunque rain forest in San Juan, Puerto Rico.

The western route offers a great blend of eco-adventures and cultural attractions, with stops along Mexico’s Yucatan Peninsula, plus Honduras, Belize, and Caribbean islands such as Jamaica and Grand Cayman. Hop in a kayak in Cozumel and paddle around one of the world’s largest coral reefs, or take an all-terrain vehicle (ATV) ride through the rain forest in Ocho Rios.

Ports on the southern route are farther apart than those on eastern and western sailings, requiring more travel time — but also providing a more exotic experience. It’s the most interesting route, calling on remote isles that make you feel as though you’re shipwrecked on “Gilligan’s Island.” You may want to ride horseback through St. Barth’s hillsides and tour St. Lucia’s Sulphur Springs, the world’s only “drive-in” volcano. While the idea of escaping to a tropical island paradise may have been the initial inspiration for a visit, you’ll quickly learn there’s a lot more to the Caribbean than just sun, sand, and surf. 

When to go

Photo by Thinkstock

With year-round balmy weather, it may seem like anytime is a great time to cruise the Caribbean. However, there are some important points to consider before booking.

Hurricane season — which runs June 1 through November 30 — is the main issue, with an average of six hurricanes a year. The Southern Caribbean was once thought to sit under the hurricane belt and remain unaffected by storms, but with Grenada and Aruba both hit in the last 10 years, it’s a concern no matter which route you take.

Even with hurricane season in full effect, families and honeymooners still frequent the islands over the summer, so prices usually don’t go down. Late summer to fall is when you can find the best deals, as well as in early December (right after Thanksgiving) and January (right after New Year’s).

High season for both the Western and Eastern Caribbean is December through April, when most people are looking to flee the harsh winter up north. September through October and late April — depending on when Easter falls — through May are considered the shoulder seasons, so ships and ports are often less crowded.

Our advice: Avoid Christmas, summer, and spring break if you’re looking for a quiet, relaxed vacation. 


There Are Four Main Routes to Choose From: 


Eastern Caribbean: Nearly every cruise line, big and small, offers itineraries on this route, with sailings ranging from three nights to the traditional seven , and up to 10 nights and longer. Main ports include U.S. Virgin Islands (St. Thomas, St. Croix, and St. John), British Virgin Islands (Virgin Gorda and Tortola), plus San Juan, Puerto Rico; St. Martin; and Grand Turk, Turks and Caicos.

The biggest decision won’t come in choosing an itinerary but an embarkation port. Cruising out of Fort Lauderdale, Florida, and Miami are very popular choices since they provide less time at sea before the first port of call. But flying down to Florida is no longer necessary for New Englanders, with several embarkation choices along the East Coast: Manhattan and Brooklyn, New York; Bayonne, New Jersey; Baltimore, Maryland; and Charleston, South Carolina. You can also fly to San Juan and embark from there.


Western Caribbean: With a mix of Central American and Caribbean ports, the cultural and scenic diversity of this route makes it a great choice for first-time cruisers. Even those who have sailed it before can uncover new things with a variety of itinerary options from which to choose.

Four- or five-night sailings typically stop in Cozumel; Key West, Florida; Jamaica; and Grand Cayman, while seven-night cruises may add on Roatan, Honduras; Belize City, Belize; and Costa Maya, Mexico. Most big-ship lines embark from southern cities such as New Orleans; Galveston, Texas, or Houston; Miami, Fort Lauderdale, or Cape Canaveral, Florida.


Southern Caribbean: This route is different than the others in terms of travel requirements and port personalities. Standard weeklong itineraries require a flight to the embarkation port — typically San Juan or Barbados — since it’s too far to sail to from the U.S. Those planning a 10-night or longer vacation can choose to leave from domestic ports such as Florida’s Miami, Fort Lauderdale, Tampa, and Cape Canaveral, or New York City.

Southern Caribbean itineraries commonly make stops in some combination of the ABC islands — Aruba, Bonaire and Curacao — as well as St. Kitts, St. Lucia, Grenada, St. Vincent, the Grenadines, and Barbados. Seasoned travelers who’ve already sailed the western or eastern routes may opt for a cruise to these more exotic destinations, each offering its own unique charm. For example, Aruba and Grenada are known for their gorgeous beaches, St. Lucia for its tropical rain forests, and the Grenadine islands for their quiet, remote cays. 


Bahamas: With more than 300 days of sunshine and high temperatures that rarely leave the 80s, a low season is virtually nonexistent in the Bahamas. Whether you like to explore cultural attractions, take in a few rounds of golf, shop in local markets, join high-adrenaline excursions, or just sunbathe on the soft, white sand, these islands offer enough variety to entertain visitors with nearly any interest.

Several mainstream lines sail year-round to the islands, with itineraries that include a stop in either Nassau or Freeport, along with a day on one of the cruise lines’ private isles. You can catch a shorter three- to four-night sailing out of Florida ports such as Miami, Jacksonville, Port Canaveral, or Fort Lauderdale, but longer five- to eight-night cruises must be taken from ports along the East Coast and the South, including Charleston, New Orleans, and Galveston. 

Cruise Lines That Sail Caribbean

29 Ships - 129 Cruises
Carnival Cruise Lines

15 Ships - 61 Cruises
Celebrity Cruises

18 Ships - 11 Cruises
Costa Cruises

4 Ships - 18 Cruises
Crystal Cruises

3 Ships - 3 Cruises

4 Ships - 55 Cruises
Disney Cruise Line

14 Ships - 107 Cruises
Holland America Line

19 Ships - 42 Cruises
MSC Cruises

17 Ships - 86 Cruises
Norwegian Cruise Line

6 Ships - 27 Cruises
Oceania Cruises

21 Ships - 44 Cruises
Princess Cruises

5 Ships - 53 Cruises
Regent Seven Seas Cruises

28 Ships - 152 Cruises
Royal Caribbean

9 Ships - 21 Cruises

13 Ships - 34 Cruises
Silversea Cruises

7 Ships - 8 Cruises
Viking Ocean Cruises

1 Ships - 7 Cruises
Virgin Voyages

6 Ships - 38 Cruises
Windstar Cruises

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