Caribbean Cruises: Everything You Need to Know

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The Caribbean remains the most popular cruise destination in the world, attracting millions of seafaring holidaymakers every year. With its collection of islands offering year round sunshine, it’s not difficult to see why it’s so popular.

With a cruise holiday, you have the opportunity to visit the best this region has to offer in a short space of time. It’s all waiting to be explored, from the golden sands of Barbados to Dominica’s scenic nature reserves and the laid back luxury of St Kitts.

Caribbean cruise ship
Caribbean cruises

Cruising in the Caribbean is one of the best, and often one of the only ways to island hop and see a large number of places during one trip, so even if you’re not generally a cruiser, you may find that Caribbean cruises are the ideal way to check off countries from your Caribbean bucket list.

Because of the growing number of itineraries and companies jumping on board the Caribbean cruise circuit, you’ll have dozens of choices, from budget to luxury, and just about any length of trip you want.

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🛈 Read more about what I learned from booking my first cruise on the Celebrity Silhouette. Thinking about going on a cruise in Europe? Check out our guide to Northern Europe cruises and Scandinavia cruises.

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When to Take a Caribbean Cruise

Cruises to the Caribbean are available throughout the year, but the weather is best during the months of November through to May. Prices are slightly more expensive during this period but you can expect hot, sunny days and pleasantly cool nights.

The cheapest time to cruise is from June to November which is considered the hurricane season. Prices tend to be lower during hurricane season because ships may have to change course to avoid oncoming storms which could impact the itinerary. Your trip may also get postponed or cancelled due to bad weather, but if you’re flexible and willing to take on the risk, you’ll be rewarded with much lower prices.

Another popular time to go on a Caribbean cruise is during the holidays. Thanksgiving and Christmas cruises are very popular and fill up fast. (Check November cruise offers) However, if you don’t mind planning way ahead, you can get some really great deals on holiday cruises.

The length of the cruise you want to take is also important. In the Caribbean, there are many lengths to consider. As short as 4 days or as long as a few weeks on board are typical. Check out of a few of the great deals from top ships by clicking the image to the left.

Departure Ports

miami cruise terminal
A cruise ships parked in Miami’s cruise terminal

Many Caribbean cruises begin their journey at a port in Florida such as Fort Lauderdale or Port Canaveral in Orlando, but other ports include Miami, Baltimore, New Jersey and Boston. One- to two-week itineraries are most common, with three geographic regions to choose from: Eastern, Western and Southern.

The eastern Caribbean cruise remains one of the most popular with destinations including Barbados, St Lucia and Antigua. If you’re after a long break, there are a limited number of cruise operators that offer month-long itineraries.

Caribbean Ports of Call

Willemstad, Curacao in the Netherlands Antilles
Willemstad, Curacao in the Netherlands Antilles

So, where can you go in the Caribbean? There are literally dozens of ports of call that are included on popular itineraries for you to choose from. You might find it easier to choose an area of the Caribbean that you’re interested in, then pick an itinerary to that area. Here are the main areas you’ll find included on itineraries:

Eastern Caribbean Cruises

If you’re looking for expansive, beautiful beaches, the Eastern Caribbean is unparalleled. In this area you’ll discover diverse cultures and attractions in some of the top Caribbean destinations.

  • Departure Ports: You can embark for an Eastern Caribbean cruise in Florida or Puerto Rico, or other East Coast ports like Boston, NYC, New Jersey, Baltimore, Norfolk, or Charleston.
  • Ports of Call: U.S. Virgin Islands (St. Thomas, St. John, and St. Croix), St. Martin (French and Dutch), British Virgin Islands (Virgin Gorda, Jost Van Dyke, and Tortola), Puerto Rico, and Grand Turk. Sometimes cruise ships visit smaller islands like St. Barts, Antiqua, Anguilla, Les Saintes, and Dominica.
  • Cruise Ships: Royal Caribbean Oasis of the Seas, Celebrity Summit, St. Regal Princess, Carnival Dream

Pros: The beaches are idyllic and sailing time is limited because the islands are so close together.

Cons: When many cruise ships are in port at the same time. For greater flexibility, choose to go on a private tour away from the other passengers.

Caribbean port of call

Western Caribbean Cruises

The Western Caribbean delivers miles of perfect beaches, world-class diving, swimming with sting rays, and the visiting the Mayan Ruins in Mexico.

Pros: Some of the best reefs for scuba diving and snorkeling. Chance to see the Mayan Ruins.

Cons: Many top activities can get overwhelmed with cruisers. Plan you own private tours to off-the-beaten-path excursions.

Southern Caribbean Cruises

If you’re looking at the more remote, small islands, you’ll want to choose an itinerary in the Southern Caribbean. If you’re willing to go a bit further – the Panama Canal and Costa Rica are included on some longer itineraries or as a whole itinerary by themselves.

  • Departure Ports: Barbados, St. Martin, or Puerto Rico.
  • Ports of Call: St. Lucia, Martinique, Curaçao, Barbados, Aruba, Bonaire, Grenada

Pros: The beaches are fantastic. These are some of the more exotic locations in the Caribbean.

Cons: The departure ports aren’t as easy to get to and will cost you extra to get there.

panama canal cruise
Cruise ship moves through the Panama Canal

Caribbean Cruises to the Panama Canal

Some cruise lines offer itineraries to explore the stunning engineering feat of the Panama Canal.

  • Departure Ports: Fort Lauderdale, Galvaston, Tampa, Los Angeles, Miami
  • Ports of Call: On a cruise to the Panama Canal, you’ll often get to see ports like Curaçao, Aruba and Cartagena.
  • Cruise ships: Celebrity Infinity, Carnival Freedom, Carnival Miracle, Caribbean Princess, Norwegian Star

Pros: There’s nothing quite like it. Some ships have historians aboard to tell you about the history of the canal.

Cons: The full length of the journey means it’s a long cruise (around 14 days).

See Panama Canal Cruises
Cuba water view

Cuba Cruises

A popular cruise route these days, especially for Americans, is a cruise to Cuba. American cruise ships began visiting Cuba in 2016 and there are a number of itineraries to choose from now.

  • Departure ports: Miami, Tampa, Charleston, Boston, Montreal Ports of call: Cienfuegos and Santiago de Cuba, Havana, Bermuda, Panama, Key West, Nassau, Freeport, Half Moon Cay
  • Cruise ships: Azamara Quest, Azamara Journey, Carnival Paradise, Carnival Sensation, Holland America Veendam, MSC Armonia

Pros: There are itineraries that offer immersive Cuba travel, and some that include other exciting destinations so you can see a mix of places.

Cons: Americans aren’t allowed to enter Cuba as tourists, so you have to stick with tour groups on the island.

>> Read more about Havana and visiting Cuba for Americans.

St. John's pier in Antigua
St. John’s pier in Antigua

Choosing the Right Caribbean Cruise Line

Check out dining and bar options, as well as entertainment venues on board to find the cruise perfect ship that meets all your needs. There are many ships available to choose from, including the sprawling luxury vessels offering every facility you could dream of, like on Holland America Line, Royal Caribbean or Celebrity.

Mid-range and budget options can be found on Norwegian Cruise Line and Carnival Cruises. For a more intimate experience, choose a smaller operator such as the Star Clippers or Windstar Cruises. These yacht-style boats are small enough to access remote ports and islands, and are great for avoiding the crowds of tourists.

For an ultra-luxurious holiday, the Thomson Discovery has some of the best amenities a ship can offer, such as a rock climbing wall, an outdoor cinema, a pool, a casino and bar and of course, restaurants that offer fine dining on-board. Virgin Voyages and Azamara are two other lines that offer ultra luxury cruises.

Finding the Right Caribbean Cruise Itinerary

Island Activities

scuba diving in mexico
Snorkeling and scuba diving is one of the biggest perks of a Caribbean Cruise.

Each island offers its own unique and often memorable array of activities. These can be expensive, so be sure to do your research online before departing. Many online price comparison sites allow you to see available tours for a chosen port on your day of arrival, regardless of which cruise line you’re on.

Alternatively, you might want to consider scheduling your own private excursion instead. A private excursion can provide good local knowledge and a great experience without having to join a group-led tour.

Some excursion highlights you can expect while on a Caribbean cruise include a Bob Marley tour in Montego Bay, scuba diving in the Bahamas, a hair rising zip-line over the forest canopy in Belize, or a foodie exploration in Grenada.

cruise in the caribbean

Some of the major cruise lines like Holland America and Carnival even have their own private island oasis where you can disembark and relax all day on the golden beaches and have your activities, beverages and meals covered while on the island as part of your cruise package.

With Caribbean cruises you have the freedom to explore these endless attractions. It’s a great way to travel and makes for a once in a lifetime experience. Between the beaches, the views that go on for miles, the incredible sunsets you’ll see from onboard, and the activities you’ll enjoy while in port, you can’t beat a Caribbean cruise for convenience and relaxation.


Cruising in the Caribbean is a great way to see the whole area in a short time, while not having to arrange flights between islands and book a hotel in each place.  Have you been on a Caribbean cruise? What was your favorite port of call?

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Caribbean Cruises: Everything You Need to Know

9 thoughts on “Caribbean Cruises: Everything You Need to Know

  1. Jade says:

    Informative post! I haven’t done a cruise before but I can see the appeal of visiting a few places in one go. I think I’d choose a Western Caribbean cruise. I’ve done Jamaica before but Mexico, Belize and Grand Cayman are calling for me!

  2. Lucy Smith says:

    I’ve never been a big fan of cruises before but the more I read about them the more I’m considering going. Especially one to the Caribbean, looks incredible!

  3. Elena says:

    Absolutely agree with Jade: the post is so informative and useful. With trip planning there are always one or two things that somehow get overlooked, so articles like this one help in finding answers to questions that haven’t even been asked yet.

  4. Ale says:

    Actually i must admit that i don’t like so much the idea of a cruise… but your post is really inspiring.. so, I can change my mind and try!!! Why not???

  5. Bobbi Gould says:

    With all the traveling I’ve done, I STILL have yet to make a cruise. This was a super informative post for when it actually happens! AWESOME!

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