7 Caribbean Travel Tips: How to Plan a Great Vacation

Maunday’s Bay beach; credit: Wikimedia Creative Commons license

The best Caribbean travel tips come from people who have been there many times before.

It isn’t enough to read articles about what to do or what to see unless it is written by someone who has experienced that island, cruise, attraction, resort, excursion, etc.

I clearly remember a neighbor trying to describe Stingray City in Grand Cayman. It sounded like fun. When we went, it turned out to be fantastic.

Check off these seven Caribbean travel tips when you plan your vacation.

1 - Best Way to Plan

The most important decision is whether to go on a cruise or spend an entire week (or more) at one destination. Planning begins with that decision, followed by the budget.

A cruise offers the lowest per-night cost compared to a hotel or resort stay and plenty to eat and do. It is the most budget-friendly way to travel in the Caribbean. It typically visits multiple places and has the widest number of experiences as a result.

A “stopover” or overnight vacation at a hotel or resort has the benefit of stability, freedom of movement and the chance to explore all of the best options that a destination has to offer. After more than 20 tours of the Caribbean, we like to take turns going on a cruise and visiting a hotel or resort.

In either case, it helps to discuss what you like to do the most on vacation and choose the cruise or destination that best fits your preferences. Keep in mind that attractions and shore excursions have a major impact on the budget.

Some destinations are great for beaches but not for nightlife or shopping; others are strong on watersports but not hiking and sightseeing.

2 - Best Types of Cruises

Caribbean cruises are usually divided into western, eastern and southern. Each one has advantages depending on the time of year and the excursions they provide.

Western cruises are most popular during the spring when the major destinations including Grand Cayman, Jamaica, Cozumel and Roatan have warm temperatures and low rainfall, especially in March and April. They also are popular because of great excursions such as Stingray City and Dunn’s River Falls.

One small downside to western cruises is the starting point for many people. They often have to fly to San Juan as their port of embarkation. Others may leave from Florida or Gulf of Mexico ports along the United States coast. But San Juan has plenty of its own appeal, especially the historical Old San Juan.

Eastern cruises have the advantage of convenience when ships disembark from Florida cruise ports, which are closer (and sometimes cheaper to reach) for many U.S. and Canadian travelers than San Juan. The eastern cruise ships pass through such destination as the Bahamas, Turks and Caicos, Dominican Republic, San Juan and the Virgin Islands.

Southern cruises often include Aruba and Curacao plus some of the southernmost destinations that often are part of eastern cruises, such as Barbados, St. Kitts and St. Lucia.

3 - Best Resorts and Hotels

It isn’t possible to rank the resorts and hotels because there are so many of them. But it is possible to make the best possible choice based on several important factors.

First, all-inclusive resorts are the most convenient and also the most expensive way to visit one destination in the Caribbean. They provide plenty of good food and entertainment. Most of them are concentrated on Dominican Republic and Jamaica, then scattered in smaller numbers among the remaining destinations.

They work well on Dominican Republic and Jamaica because of safety concerns and because of the lack of things to do nearby. Those resorts emphasize activities that stay on the property.

It makes less sense financially to choose an all-inclusive at many other destinations. From a budget point of view, the next best option is a hotel with a kitchenette and nearby grocery store. Good options include Aruba, Grand Cayman and St. Maarten.

Take time to shop for the best deals on major travel sites. Look not only at the prices but also at the location of the hotel and its distance to nearby shopping, dining and attractions. Comparison shop based on time of year and destination.

Getting to any hotel or resort usually requires an airline ticket. Keep in mind that distance is a factor in the ticket cost. Closer destinations such as Cancun have less expensive tickets while farther ones such as Aruba are usually more expensive.

4 - Best Islands to Visit

Although the Bahamas aren’t technically part of the Caribbean Sea, they usually are included in any guides about the region. They win the award for being the closest and most convenient place to visit for most U.S. and Canadian visitors.

Dominican Republic is the most popular destination in the entire Caribbean, according to the Caribbean Tourism Organization, because of its numerous and luxurious all-inclusive resorts in Punta Cana and Puerto Plata. Jamaica is popular for the same reason.

St. Thomas has the most well-known duty-free shopping districts, but Aruba, Cancun, Curacao, Grand Cayman, Nassau, St. Kitts, St. Maarten and Playa del Carmen also have vibrant shopping and dining districts.

Choosing the islands with the best beaches is a matter of opinion. Anguilla (Shoal Bay), Aruba (Palm Beach), British Virgin Islands (The Baths), Dominican Republic (Punta Cana), St. Martin (Orient Bay) and U.S. Virgin Islands (Magen Bay) all have famous beaches. Anguilla is our personal favorite for a combination of beauty and fewest number of people.

5 - Best time to Go

Aruba cruise port in Orangestad; © Aruba Tourism Authority

Annual statistics from the Caribbean Tourism Organization show a clear pattern throughout most of the region.

Visits spike in March during spring break for schools. They spike again from June through August and plummet in September and October during the peak months of the Caribbean hurricane season.

Avoid December and January because of cooler temperatures and ocean swimming that can be chilly in many locations. That said, December is popular because of winter break from schools.

May is often a brief rainy season for many destinations. April and June are two of the best months for a combination of warm temperatures and low rainfall.

6 - Best Excursions and Attractions

All of the Caribbean destinations have standard attractions that are found at just about any major beach in the world—snorkeling, scuba diving, windsurfing, etc. Nearly all of them have similar land activities including ATV rides, horseback rides and jeep excursions.

Certain attractions are unique, and they make the difference between a good vacation and a memorable one.

The previously mentioned Stingray City and Dunn’s River Falls are on that list. Others include Old San Juan, swimming with sea turtles in Barbados, cave tubing in Belize, touring Chichen Itza near Cancun and snorkeling the reefs at Bonaire, Belize and Roatan.

7 - Best Way to Get Around

Review destination maps to know the locations of airports, shopping, restaurants and excursions compared to the place where you plan to stay.

Find out the cost and availability of taxis and other forms of public transportation. Some of the smaller destinations have no public transportation. Taxis and excursion buses are efficient ways to get around.

Find out what you need for currency. Many destinations readily accept U.S. dollars, credit cards and traveler’s checks, but some won’t accept U.S. coins.