Thinking about taking your first cruise or searching for an inexpensive winter escape? Look no further than a Caribbean cruise offering splendid sunshine, sandy beaches and laid-back island vibes all year round. Many first-time cruisers choose the Caribbean because it’s an easy, affordable vacation with a variety of options departing from several ports in the southern United States.

With more than 700 idyllic islands dotting the Caribbean Sea, it seems this region was destined to be explored by ship. Read on for answers to some of the most commonly asked questions about cruising the Caribbean.

1. Which cruise lines are best for Caribbean cruises?

Aerial view of Royal Caribbean ship in Labadee, Haiti

Source: Royal Caribbean International; Harmony of the Seas at Labadee, Haiti

With the Caribbean accounting for more than one-third of all cruises offered globally, you’ll find that nearly every cruise line offers some version of a Caribbean cruise ranging from 4-night sailings to longer voyages spanning over 20 nights.

Royal Caribbean and Carnival dominate the Caribbean market offering a huge variety of sailings that appeal to US travelers who prefer to drive to their cruise. While the vast majority of Caribbean cruises depart from Miami or Fort Lauderdale, Carnival, Royal Caribbean (and sometimes Norwegian) offer round-trip sailings from New Orleans, Port Canaveral, Galveston, and Tampa for various durations.

For a short but more upscale experience, 5-night sailings are offered by Celebrity and Disney Cruises. For something a bit different, roundtrip sailings from Puerto Rico are also a great option offered by Carnival, Celebrity and Royal Caribbean.

2. What is the best time to go on a Caribbean cruise?

A hidden beach destination in a Caribbean cruise

Source: Shutterstock

The Caribbean boasts generally good weather year-round, however, storm season does peak between August and October which could mean rougher seas and a higher chance of seasickness. December through April is the most popular time for Caribbean cruises because of the low chance of rain and the general desire to escape the winter chill further north at this time of year.

For a glimpse into local island culture, you may consider planning your cruise around special Caribbean events. Join the party and take in the colorful costumes at Trinidad and Tobago’s Carnival celebrations which happen in late February or early March. Or bring the kids along for the annual Pirates Week Festival invading the Cayman Islands each November with loads of swashbuckling fun. 

3. Should I choose an Eastern Caribbean or Western Caribbean cruise?

Caribbean stop at the Mayan pyramids

Source: Shutterstock, Mayan pyramid at Chichen Itza

When you begin to plan your Caribbean cruise, you’ll notice itineraries are usually divided between Eastern Caribbean and Western Caribbean. So what’s the difference?

If you’re looking for a short four or five-night cruise, or a sailing departing from Galveston, New Orleans or Tampa, you’ll find many more options available for Western Caribbean cruises. These also tend to be cheaper than their Eastern Caribbean counterparts.

While both itineraries offer stunning vistas, crystal clear waters and carefree culture, Eastern Caribbean ports are generally more known for their beautiful beaches and phenomenal shopping. Western Caribbean ports, on the other hand, may appeal more to adventure seekers with excellent diving, snorkeling and caving excursions available. Since Western Caribbean cruises call on ports in Mexico and Central America, there is also plenty of interesting Mayan culture to explore.

You may also notice that Southern Caribbean cruises are another option which generally depart from embarkation points outside the continental US like Puerto Rico, Barbados, or Martinique. Since these itineraries begin farther south, they include less busy ports closer to South America and give you the chance to extend your vacation in the Caribbean by adding a few extra days before or after your cruise.

4. Where does a Caribbean cruise take you?

A Caribbean cruise in Puerto Rico

Source: Norwegian Cruise Line; Norwegian Gem at San Juan, Puerto Rico

With more than 80 cruise ports in the Caribbean, there is a ton of variety in itineraries and so much to explore. Here are a few of the Caribbean port highlights.

For the beach bum: Grand Cayman Island

There’s no shortage of gorgeous beaches in the Caribbean but Grand Cayman’s Seven Mile Beach is a standout just a 30 minute walk or five minute taxi ride from the cruise terminal. Nearby you’ll find the popular Stingray City attraction where you can feed and swim with these magnificent creatures.

For the history buff: San Juan, Puerto Rico

The energy and history of this beautiful walled city is easy to explore with free trolleys and an old town ideal for strolling. Tourist areas have fully recovered from Hurricane Maria but locals will still benefit immensely from the dollars you spend while in port.

For the foodie: St. Martin / St Maarten

Amiably split between the French and the Dutch since 1648, St. Martin is a unique melding of cultures on one tiny island. St. Martin’s French side in particular is a renowned culinary destination showcasing interesting French-Caribbean fusion dishes which can be enjoyed on a budget each Tuesday at the Mardis de Grand-Case street fair.

For the shopaholic: St. Thomas, US Virgin Islands

Whether you’re looking for diamonds, cameras or a new designer watch, St. Thomas is the place to shop ’till you drop. With hundreds of duty-free shops lining the streets of the capital city, Charlotte Amalie, US visitors will be tempted to take advantage of the island’s special exemption allowing them to take home $1,600 worth of goods duty free.

5. Best Caribbean shore excursions

Dunn's River Falls, major Caribbean tourist attraction

Source: Getty Images; Dunns River Falls, Ocho Rios, Jamaica

Natural wonders, exhilarating adventures, historical treasures–the Caribbean really does have something for every type of traveler. Here are some of the best Caribbean shore excursions to consider.

Rent a clear-bottom kayak in Cozumel, Mexico

With one of the largest coral reefs in the world just off its shores, Cozumel is an amazing place to observe the rich marine life on a snorkeling or kayaking excursion. If you prefer to stay dry, rent a clear-bottom kayak from Playa Uvas and take in the colorful array of fish as you paddle your way around the reef.

Spend a half day volunteering in Barbados

Though the Caribbean may be rich in sand and sunshine, it’s also one of the most impoverished regions in the world. Consider spending a portion of your cruise giving back to the islands by volunteering with a local charity. During a four-hour shore excursion in Barbados through Hope Floats, you’ll help to deliver a local lunch program that has been serving Barbados’ underprivileged for years.

Climb a waterfall in Ocho Rios, Jamaica

Visiting Ocho Rios’ famous Dunn’s River Falls is truly a magical experience. An impressive matrix of small cascading waterfalls in the lushest of settings, you can relax in the natural pools or enjoy climb up falls themselves with the help of a trusted guide.

Visit the birthplace of Alexander Hamilton in Nevis

Most cruise lines stop at St. Kitts, but the nearby island of Nevis is a short ferry ride away and a worthwhile day trip. Although visiting Nevis, the birthplace of Alexander Hamilton, may give you Broadway bragging rights, there’s much more to discover here including lovely Pinney’s Beach, old plantations and the ever-present volcano ascending from the center of the island.


We hope you found this article useful in planning your first or next Caribbean cruise! With so many different itineraries, departure points and exciting excursions to discover, you’re bound to find a Caribbean cruise that’s the perfect fit for you.


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