Caribbean Island Vacation Tips for 1st Timers

First-time Caribbean vacationers have to choose between an all-inclusive resort or a cheaper hotel. Credit: Wikimedia Creative Commons license

Anyone planning a Caribbean vacation for the first time will find it hard to imagine the fun and beauty that awaits them.

Nothing is quite like walking into a huge, open air lobby of a Caribbean all-inclusive resort for the first time.

On our first trip of many, wonderful trade winds washed through the resort lobby. The colors of the lobby decorations were bright and uplifting.

The friendly resort staff offered easy guidance through checking in and leading visitors off to the building on the resort complex that had our rooms.

We walked under palm trees, past curving pools and waterfalls and around open-air restaurants. We sometimes forgot to pay attention to the sidewalk.

We changed quickly into resort clothes or bathing suits and found a beach with amazing white sand and emerald ocean water beneath more palm trees.

If handled right, an all-inclusive resort guarantees a week of relaxation with everything packaged into one convenient vacation.

Less Expensive Hotels

All-inclusive resorts are expensive because they include, well, everything, such as room, food, drinks and entertainment.

© Scott S. Bateman

The alternative is the unpackaged hotel experience. Choose a hotel and have the freedom to walk the streets of a city or village, pick a restaurant on whim that may or may not be great.

The spontaneity makes for great moments when a couple sits at a table by the ocean and everything seems to sparkle in a dream.

Unlike the controlled pace of a cruise, an overnight Caribbean vacation is best for travelers willing to do a little research into the best hotels and locations.

They also need to take some time to decide exactly what kind of vacation feels right—slow and easy, highly active, spontaneous, big on shopping or big on recreation, etc.

10 Great Caribbean Destinations

We have visited all 10 in the list below plus many more. Our pick for 10 great Caribbean vacation destinations are:

1. Dominican Republic

Great beaches and all-inclusive resorts, light on things to see outside of resorts. But the resorts offer so much to do that going outside of them usually doesn’t matter.

2. Jamaica

Lush vegetation; fascinating people, dialect and culture; famous excursions such as Dunn’s River Falls and Dolphin Cove in Ocho Rios. Take your pick of Ocho Rios, Negril or Montego Bay.

3. Cancun

During spring break, it’s a great place for college students to just hang out and party. Otherwise, it’s a convenient and low-risk choice for people who love everything in one location. It also has one of the most amazing Caribbean attractions at the nearby Mayan ruins of Chichen Itza.

4. Bahamas

Easy and convenient access off the coast of Florida. The visit most likely to be used for a short hop over a long weekend. Nassau is the most popular cruise port outside of Florida.

5. Puerto Rico

A place to spend time for a few days before or after a cruise out of the port of San Juan to the western or southern Caribbean. It also has one of the best historical attractions in the Caribbean at Old San Juan.

6. Aruba

The top choice to visit to avoid hurricanes during the hurricane season. Dutch culture adds a distinctive European flavor to people staying at hotels in the capital of Oranjestad. It’s also one of the warmest and driest islands in the Caribbean.

7. U.S. Virgin Islands

The shopping mecca of the Caribbean at Havensight Mall and Charlotte Amalie. It has a great beach at Magens Bay.

8. Barbados

An up and coming resort destination. Its most famous attraction is a chance to swim with sea turtles.

9. Martinique

High on Caribbean French culture and lush, beautiful landscapes. It offers one of the most authentic French cruise ports in the Caribbean.

10.St. Maarten

More French and Dutch culture packed into two sides of one small island. Philipsburg is one of the Caribbean’s best cruise ports.