© 2023 Scott S. Bateman

Travelers who plan to go on their first Caribbean cruise may find the process is complicated in many ways.

Should we go on a western, eastern or southern Caribbean cruise? When is the best time to go for weather? What will it cost? How long should we go? Should we go on expensive shore excursions? If so, which ones?

Which cruise line should we take? Should we get an expensive ship cabin with a balcony or a budget-wise interior cabin?

Getting good answers to these questions is important because a wrong decision could lead to a frustrating vacation costing thousands of dollars.

Best Cruise Destinations

Cruise lines usually divide Caribbean cruises into three major regions: western, eastern and southern. Western and eastern are the most popular.

Western destinations include such major islands as Jamaica, Cozumel and Grand Cayman. They sometimes include secondary destinations such as the island of Roatan and Costa Maya on the Mexican coast.

Some of them also go to Central American countries such as Belize, Costa Rica and Panama.

Western destinations have some of the best excursions including Stingray City at Grand Cayman, Dunn’s River Falls in Jamaica and cave tubing in Belize.

Eastern cruises offer a wider variety of islands to visit. They include Antigua, Barbados, Dominica, Dominican Republic, Martinique, Puerto Rico, St. Kitty, St. Lucia, St. Maarten, Turks and Caicos, and the U.S. and British Virgin Islands. Ships leaving from Florida often visit the Bahamas, which are just north of the Caribbean Sea.

Southern cruises have the advantage with weather, especially during winter months. Those destinations are often warmer and drier, especially Aruba, Bonaire and Curacao. Southern cruises usually include some of the eastern islands as well. Ships often disembark from San Juan, Puerto Rico.

Time of year is a big factor in which one to choose. Western is best during early spring because of the dry season with weather. Eastern is good from early spring to early summer for the same reason, plus warmer temperatures. Southern is ideal during the winter and spring for warm temperatures plus a dry season.

Best Times to Go

But what about summer and fall cruises? The annual Caribbean hurricane season is a major factor in planning summer and fall cruises.

The hurricane season officially begins June 1 and ends Nov. 30. But June and November rarely get hurricanes and tropical storms. The season gets more active in July and climbs until reaching the high point for hurricanes and tropical storms in September and early October.

It’s important to note that hurricanes rarely hit islands directly. Instead, they pass through the region and bring heavy rains and strong winds to Caribbean destinations.

September and October are the worst times to go on a Caribbean cruise. But it doesn’t stop some people from going then. They may live near the embarkation ports and can drive there for last-minute cruises if they see the weather forecast looks good for the week ahead.

People who live farther away, want to cruise in the summer and can’t buy airline tickets at the last minute—which is usually when they are most expensive—should plan instead to cruise in early summer. The risk of rain is lower than during late summer.

Western cruises are most popular from December through April because it is a dry season for many of the western destinations.

What Will It Cost?

The cost of a Caribbean cruise depends on six big factors:

1. The length of the cruise.
2. The cruise line.
3. The available cabins.
4. The location of the ship cabin.
5. The number and cost for excursions.
6. Purchases on shore.

Stingray City is a memorable shore excursion. Credit: Wikimedia public domain

The most basic decision for a cruise planner is choosing the number of days to go on the cruise. For example, the most common cruise is six to nine nights long. Other cruises are as short as three to five nights and some go more than two weeks.

A simple calculation helps cruise planners with comparing prices. Simply divide the total cost by the number of nights to get a cost per night. Use that number to compare cruises with a different number of nights.

Still, seven-night cruises are especially common. Someone might do extensive searches on major travel websites, see a long list of seven-night cruises and find a wide variety of prices. Why do they vary so much even for the same number of nights?

The prices in those cases depend on the cruise line and the availability of cabins.

Disney Cruise Line is often one of the most expensive. Carnival and Norwegian are among the least expensive. Their costs depend largely on the quality of food, entertainment and amenities.

Cabin costs fluctuate over a period of many months depending on how many are available. The price of the same cabin can be quite high six months before the cruise and much lower six days before the cruise if it’s still available. Cruise lines don’t like empty cabins.

The size and location of the cabin also is a major factor in prices. Cabins range from tiny interior cabins with no windows to massive three-bedroom suites with large balconies.

Smart shoppers will first choose their cabin size and location. Then they will watch cabin prices over a period of at least weeks if not months until the right price comes along.

The final costs come along on the cruise itself. Cruise lines try their best to get passengers to spend money on the ships and buy everything from artwork to jewelry, liquor, clothing and spa treatments.

In port, passenger discover many more ways to spend money, especially shopping and shore excursions.

Cruise planners may find it will help to start with a budget such as $1,000 per person. Subtract the essential cruise costs such as the cruise price (plus fees and port taxes). Whatever is left can go to on board and on shore expenses.

Shore Excursions

Shore excursions make a Caribbean cruise much more memorable. The best shore excursions are unique. For example, Stingray City at Grand Cayman is a rare opportunity to snorkel with stingrays that are comfortable around people. Few places in the western hemisphere offer a chance to go tubing through an underground river like the one in Belize.

Cruise passengers can find plenty of tourist attractions in port that cost little to no money, such as touring Old San Juan in Puerto Rico. But some of the best ones do come at a cost.

Most shore excursions cost between $50 and $100 per person, although some are cheaper than $50 and others like swimming with dolphins will cost more than $100. Budget accordingly.