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Two Women Snorkeling in the Bahamas (Photo: Dudarev Mikhail/Shutterstock)
Two Women Snorkeling in the Bahamas (Photo: Dudarev Mikhail/Shutterstock)

Everything You Need to Know About Eastern Caribbean Cruises

Two Women Snorkeling in the Bahamas (Photo: Dudarev Mikhail/Shutterstock)
Two Women Snorkeling in the Bahamas (Photo: Dudarev Mikhail/Shutterstock)
Executive Editor, U.S.
Chris Gray Faust
Carolina Pirola

Last updated
Dec 20, 2023

Read time
8 min read

Eastern Caribbean cruises come in abundance, with nearly every cruise line offering up some type of itinerary that either concentrates on the region or at least touches a port or two.

While veteran cruisers may yawn at the thought of yet another call at an Eastern Caribbean cruise stalwart like St. Thomas, St. Maarten or Nassau, the region is first-rate for first-time cruisers.

That's because these ports of call are among the Caribbean's most developed for tourists, offering well-organized activities, from duty-free shopping to watersports and tours of historic sites.

That being said, an Eastern Caribbean sailing truly does have something for everyone. Here are eight tips to help you plan the itinerary that best suits you.

1. Eastern Caribbean Cruises Encompass More Destinations Than You May Think

The Paradise like US Virgin Islands, St. Thomas Showcasing a Turquoise Ocean and Lush Landscapes (Photo: Achim Baque/Shutterstock)
St. Thomas, US Virgin Islands (Photo: Achim Baque/Shutterstock)

Technically, the Eastern Caribbean region encompasses the British Virgin Islands and American Virgin Islands, Puerto Rico, and the two-nation-one-island St. Maarten and St. Martin. We also include sailings to the Bahamas -- which is not officially part of the "Caribbean" -- and Grand Turk in Turks & Caicos because stops there are such a major part of so many Eastern Caribbean itineraries.

Many Eastern Caribbean cruises also include a stop at cruise line private islands such as Royal Caribbean’s CocoCay, Half Moon Cay (Holland America), Great Stirrup Cay (Norwegian Cruise Line) or Princess Cays.

2. Cruises to the Eastern Caribbean Vary by Season

Woman Snorkeling Near Shallow Reefs in St. Maarten (Photo: Fabio Lamanna/Shutterstock)
Woman Snorkeling Near Shallow Reefs in St. Maarten (Photo: Fabio Lamanna/Shutterstock)

Picking the right time to cruise the Caribbean is as important as choosing the right itinerary. Cruises to the Eastern Caribbean are offered year-round, but the demographics of your fellow cruisers will vary depending on whether it’s high or low season.

"High" season in the Eastern Caribbean typically begins in December and runs through April, luring those who want to flee winter in the U.S., Canada and Europe. It’s common to find a good mix of retired couples and groups of young friends on these sailings.

Some cruise lines offer summer cruises to the Eastern Caribbean, which is an increasingly family-oriented destination. These sailings are particularly busy and boisterous during school holidays.

The only major difference between winter and summer in the Eastern Caribbean is a slightly warmer climate -- but it's not as searingly hot in summer as you might expect.

Late summer and fall, especially when kids go back to school, is when cruise lines offer the best bargains. We must include a caveat, however: Hurricane season runs from June 1 to November 30. Particularly in the traditionally stormy months of August, September and October, extreme weather can wreak havoc with your cruise vacation.


3. Research Cruise Lines Before Picking a Cruise to the Eastern Caribbean

Close-up of a coconut-carved drink at Ocean Cay MSC Marine Reserve, with ship docked in the background
Drink at Ocean Cay MSC Marine Reserve (Photo: Brittany Chrusciel/Cruise Critic)

Almost every cruise line, big and small, offers itineraries in the Eastern Caribbean. While luxury cruise lines tend to avoid the highly trafficked ports, like St. Thomas, you'll find their ships mixing in a few smaller Southern Caribbean ports such as St. Barts or Dominican Republic.

Even European-based lines, such as MSC and Costa, have been placing ships in the area. These cruises are aimed at attracting not only new North American customers, but international passengers looking for a short cruise to add to a longer holiday.

Since you’ll be spending a lot of time onboard your cruise ship, don’t decide based only on itineraries. Each cruise line offers a slightly different onboard experience. Some are all about family-friendly fun, while others focus more on upscale dining and offer a more traditional cruise experience.

4. Plan Out Activities and Excursions at Your Ports of Call on Your Eastern Caribbean Cruise

Beach chairs and umbrellas along Cabbage Beach in Nassau on a sunny day
Cabbage Beach in Nassau (Photo: Gaston Piccinetti/Shutterstock.com)

Although some people may believe that the phrase “seen one, seen them all” applies to Eastern Caribbean ports more than to any other destination, each stop offers something different. It’s not all beach and sun in the region, and with a little bit of research you’ll be able to make the most of your days on land.

Nassau, Bahamas: The Straw Market is a Nassau tradition, and you'll find all sorts of souvenirs on sale, from thatched purses to hair-braiding. If you'd rather just spend the day as a guest at the showy, 34-acre Atlantis Resort, consider purchasing a day pass. Beach lovers will want to hit Paradise Island, where you can find all manner of water-sports rentals and eateries.

Grand Turk, Turks & Caicos: This small island chain's claim to fame is its powdery white sandy beaches, and position on a major coral reef. Watersports such as diving, snorkeling and catamaran excursions are popular. Cockburn Town contains the governor's house, old churches, the public library and a small plaza containing the Columbus Monument, which claims that the explorer landed there in 1492.

St. Thomas, U.S.V.I.: Charlotte Amalie in St. Thomas is easily walkable and a duty-free shopping haven (although bargains are not always as good as they seem). Magens Bay wins praise as one of the Caribbean's top beaches, but for a true snorkeling adventure, take the ferry over to St. Johns.

Tortola, British Virgin Islands: It's all about beaches and watersports in this gorgeous corner of the Caribbean called Tortola, although hiking and shopping are also popular.

Take the ferry to Virgin Gorda and snorkel and swim among the prehistoric boulders that make up "The Baths." Or head over to Jost van Dyke and indulge at some of the region's most famous beach bars. (We like Foxy's and Soggy Dollar.)

San Juan, Puerto Rico: Visit Old San Juan's most historic monuments, particularly El Morro, with original sections that date back to the 16th century. If you have longer in port, don't miss El Yunque. It's the only rain forest designated as a U.S. National Forest where you can see numerous waterfalls, ferns and wildflowers along the marked trails.

St. Maarten/St. Martin: You get two cultures for one stop, as the Dutch and French sections of the dual island have retained their heritage. Philipsburg on the Dutch side is the hub, with streets crammed with duty-free jewelry shops, electronics (bargaining recommended) and liquor. Marigot is the capital of the French St. Martin, and is filled with designer boutiques and fabulous restaurants, bistros and cafes.

Adventure junkies (or aviation enthusiasts) won't want to miss Sunset Beach Bar which sits at the end of the runway at Princess Juliana International Airport. St. Maarten is also a good jumping off point for day trips to Anguilla, St. Barts and Saba.

5. Your Embarkation Port Could Determine the Length of Your Cruise to the Eastern Caribbean

Choosing an itinerary is pretty easy as most ships visit the mainstream ports such as the U.S. Virgin Islands' St. Thomas and St. Maarten in the Netherlands Antilles. More challenging in planning your cruise is determining your embarkation port and your cruise length; these are only complicated because there are so many options from which to choose.

Voyages not only depart from the region's major jumping-off points (Miami and Ft. Lauderdale's Port Everglades) but also other East Coast ports ranging from New York City to Charleston. You can even go on a cruise to the Eastern Caribbean from Europe -- during seasonal repositionings in spring and fall.

As for length, these cruises range from perfect-weekend, three- or four-night jaunts to 10 nights and beyond. Since your embarkation port will determine your options in terms of length, make sure you know what’s feasible before spending hours doing research on ports of call.

Short cruises generally depart from Miami, Fort Lauderdale or Port Canaveral. These ports also offer plenty of seven-night voyages.

Baltimore, New York, Charleston and Jacksonville have become home bases for seasonal Caribbean trips, both short and long. However, because of the extra time it takes to get down to the islands, expect a few more sea days and weather that might not be the warmest until you reach a lower latitude.

6. Dare to Explore on Your Own and Look into Car Rentals in Eastern Caribbean Ports of Call

Diving off the Turks and Caicos Islands in the Caribbean Sea (Photo: Ethan Daniels/Shutterstock)
Diving off the Turks and Caicos Islands in the Caribbean Sea (Photo: Ethan Daniels/Shutterstock)

While official and independent shore excursions abound in the Eastern Caribbean, renting a car on islands such as St. Maarten or Puerto Rico is usually easy and not too expensive. Make sure you book in advance, as vehicles can go quickly when several ships are in port.

Don't be dissuaded by the ports' touristy vibe. While some Eastern Caribbean stops can seem overwhelming when you disembark, you can find peaceful beaches and friendly hangouts not too far out of town. Do some research ahead of time, and you can find your slice of paradise on even the most crowded days.

7. Don’t Let Your Guard Down: Keep a Lookout for Pickpockets in the Eastern Caribbean

Just because you're sailing in the Eastern Caribbean doesn't mean you should leave your wits at home. Serious incidents are rare in most destinations, but crowds of tourists trying to find their way around unfamiliar places are often targets of scams and pickpockets.

Beyond watching your wallet and not leaving your valuables at the beach unguarded, apply the Three-Step Program: Assess the risks. Research the risks. Minimize the risks.

8. Be Open-Minded and Aware: Not Everything Will Be Like at Home

St. Barts (Photo: Edd Lange/Shutterstock)
St. Barts (Photo: Edd Lange/Shutterstock)

The character of the islands is often determined by the original settlers. Don't be surprised to see “European,” i.e., topless or nude, beaches on islands such as St. Martin or St. Barts (don't worry, there are plenty of clothed beaches for families too).

Even if discovering other cultures and traditions is not your number one reason for going on an Eastern Caribbean cruise, embrace the differences and enjoy the trip. You will probably find fun, interesting things to do and learn along the way.

Find additional information to help you plan your next cruise to the Caribbean with us today!


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