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One Day in a City > Cruises > How to Choose the Best Caribbean Cruise Itinerary

How to Choose the Best Caribbean Cruise Itinerary

March 7, 2024 By Gina
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Breaking Down the Cruise Regions of the Caribbean

Cruise ship sailing by the Caribbean port of Curacao
Cruise ship sailing by the Caribbean port of Curacao

Does this scenario sound familiar? You know you’d like to go to the Caribbean, and you know you want to go on a cruise, but as soon as you start looking into Caribbean cruises to plan your trip you get quickly overwhelmed. Why? Because the Caribbean is the most popular cruise destination in the world and there are numerous different types of itineraries. 

Plus, it’s not just that there are a lot of itineraries. The Caribbean is also home to different regions — each of which in turn has multiple itineraries to choose from. After all, there are over 40 ports of call in the Caribbean that the main cruise lines visit.

While this makes it amazing to find an itinerary perfect for your interests and travel style, this wide range of choices also can make cruise planning overwhelming. If you’re not a cruise expert or super knowledgeable about the Caribbean, it’s easy to get confused about which Caribbean cruise is best for you.

Lucky for you, I am a cruise expert and am here to help! I’ve worked in the cruise industry as a marketer and writer for over 15 years. I have cruised solo, as a couple, and with kids.

In this article I’m going to help make the planning process easier for you so you are free from vacation planning overwhelm and stress and can put together your perfect Caribbean cruise vacation. 

Cruise Regions of the Caribbean

Cruise lines typically segment the Caribbean into three different regions: the Western Caribbean, the Eastern Caribbean, and the Southern Caribbean. Some itineraries overlap and visit islands that are in more than one of those regions, while others tend to stick to just one area of the Caribbean. 

Understanding what each region offers and how that correlates to your favorite activities and personality type can help you choose the best Caribbean cruise itinerary for you and your travel partners. 

Western Caribbean Cruises

Let’s look at the islands of the Western Caribbean first.

Western Caribbean cruises typically include the islands of Grand Cayman and Jamaica. In addition, Western Caribbean cruises often visit Mexico ports of call; common ones are the Mexican island of Cozumel and the port of Costa Maya, an adventure-filled tourism hub that borders the Caribbean Sea. 

The Western Caribbean is a great destination for those looking for shorter cruise itineraries that are five to seven nights in length since it doesn’t take long for cruise ships to get to the ports of call in the Western Caribbean, particularly when embarking from Florida cruise ports. 

The Western Caribbean is also known for its excellent water sport activities and adventures. You can scuba dive and have the chance to see whale sharks off the coast of Cozumel, swim with stingrays in the Cayman islands, or spend the day at an adventure park in Costa Maya where you can partake in zip lining, river rafting, and more. 

For a more far-flung Western Caribbean itinerary that will also let you check multiple countries off your list, opt for one that sails all the way down to Central America and visits cruise ports in Belize and Roatan. 

These Central America cruise ports offer travelers the chance to see the region’s historic sites and learn more about what it’s like to live and work in Central America. Plus you can visit natural wonders like the Mesoamerican Barrier Reef off the coast of Belize, which is a prime snorkeling and scuba diving location. 

Eastern Caribbean Cruises 

The Eastern Caribbean is a great region to visit for those who love the beach lifestyle. The Eastern Caribbean is home to both the U.S. Virgin Islands and the British Virgin Islands, and you’ll also find popular island destinations like St. Maarten, St. Kitts, Puerto Rico, Antigua, and the Dominican Republic within its vicinity. 

On an Eastern Caribbean cruise, you can spend your days lounging on soft white sand that make up beautiful beaches, explore the colorful beach towns where are you can do some duty-free shopping, or get a delicious cocktail by the harbor. 

Depending where your port of call is, the Eastern Caribbean also provides opportunities for cruisers to do shore excursions that take you from the big islands where your cruise ship docks to tinier ones, often home to just a small village and usually covered in tropical foliage and national parks. For example, in St. Thomas you can do a shore excursion to the smaller island of St. John. While in port in the British Virgin Islands you can take a short boat ride from the port island of Tortola to the small, lush island of Jost Van Dyke. 

The Bahamas

Eastern Caribbean itineraries also will sometimes visit the Bahamas so if you have a love for the Bahamas or want to visit some of those islands, an Eastern Caribbean itinerary is a great option, especially if you want to visit the Bahamas on a longer vacation and not one of the shorter Bahama-specific itineraries that are usually only two to five nights. 

If on a shorter Bahamas itinerary, you’ll typically embark from Miami or Fort Lauderdale, and spend a couple nights in King’s Wharf with a day at sea at the beginning or end of your cruise. 

The Bahamas are not technically in the Caribbean (the Bahamas archipelago is actually located within the Atlantic Ocean, not the Caribbean Sea), but most people lump them into the region as well due to their extremely close proximity. 

Southern Caribbean 

The Southern Caribbean encompasses the ABC Islands, a trio of Dutch territory islands located just north of Venezuela. These islands are Aruba, Bonaire, and Curacao. The Southern Caribbean then continues farther east from the ABC Islands to include the islands of Trinidad and Tobago, Granada, St. Vincent, Barbados, and St. Lucia. While it’s common to see some of these islands in the Eastern Caribbean due to their close proximity, St. Lucia is generally considered to be the start of the Southern Caribbean with everything north falling into the Eastern Caribbean region. 

Southern Caribbean cruises are often more expensive due to their remote location. This is mostly because of two reasons: length of the cruise and embarkation port. 

Southern Caribbean cruises that depart from Florida and sail to the southern Caribbean typically have longer itineraries to account for the extra sailing days needed to get so far south. Longer itineraries are going to cost you more money than a shorter one, just as if you were staying in a hotel and had to pay for additional nights. 

The other reason Southern Caribbean itineraries can be more expensive for travelers is because of flight cost. A common embarkation port for southern Caribbean itineraries is San Juan, Puerto Rico, which can be more costly to get to than mainland U.S. embarkation ports, depending where a traveler is flying from. 

Still, many people consider the potential cost of a Southern Caribbean cruise to be well worth it. Such an itinerary will take you to the desert landscape of Aruba, brilliantly framed by a bright turquoise sea; to the colorful city of Willemstad, Curacao; to the emerald hued peaks of St. Lucia; and the laidback beaches of Trinidad and Tobago. It’s a great region of the Caribbean to truly settle into the island lifestyle frame of mind while still taking in breathtaking scenery and cultural activities that teach you about the history and way of life in the Caribbean. 

More About Choosing a Caribbean Cruise

Still not sure what Caribbean cruise trip and ship is best for you? Check out my “Why You Hated Your Cruise” article, which has a detailed list of things to avoid and what to consider when choosing a cruise line and itinerary.

You can also check out my Caribbean cruise packing list and cruise daypack checklist to start getting a head start on what you’ll need to put in your suitcase.

About Gina

I'm a former travel agency marketing director turned freelance travel writer. My editorial and copywriting work has been published on and in USA TODAY, Travel + Leisure, the Travel Channel Cities app, TripSavvy, and many more online and print publications. I especially love sharing my knowledge of traveling with limited vacation time, making the most of cruise ports of call, and vacationing with kids. I also enjoy sharing my favorite travel gear and products to make traveling easier!

About One Day in a City

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Hi! I'm Gina, a former cruise and tour marketing director turned independent travel writer who helps those short on time make the most of their travels, even if you just have 24 hours to spend somewhere. Read More...

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