“The Caribbean” by any other name would still be an unforgettable destination…and trust me; it has a lot of names. Greater Antilles, Lesser Antilles, West Indies, Lucayan Archipelago, Winward, Leeward – you name it!

After many President’s Club trips, over many years, I consider myself a bit of an expert on incentive travel in the Caribbean. In the next few weeks, I will share some group travel information and knowledge I’ve collected along the way, but before I do, l think it’s important to understand what exactly we mean when we say “The Caribbean.”

The name itself conjures up images of sun, surf, and sand. You can almost see your incentive program attendees dancing to the reggae and calypso music and smell the coconut and sea salt on the soft ocean breeze. You’ve taken your top performers to an island in the Caribbean ocean, but where exactly are you?

Officially, the Caribbean is defined as a region that consists of the Caribbean Sea, its islands, and the surrounding coasts. It’s southeast of the Gulf of Mexico and the North American mainland, east of Central America, and north of South America.

Let’s break that down a little.

The region is called the Caribbean. The islands themselves are an archipelago (a Greek term for an island group or chain) that is referred to as the West Indies. Feel free to indulge your inner history geek with more information.

The West Indies is made up of 3 smaller entities; the Greater Antilles, the Lesser Antilles, and the Lucayan Archipelago. Stay with me…

Greater Antilles + Lesser Antilles + Lucayan Archipelago =
West Indies (aka the Caribbean)



There are four (4) Greater Antilles islands, which are the largest of the bunch: Cuba, Hispaniola (Haiti and the Dominican Republic), Jamaica, and Puerto Rico.

While clients are starting to ask, and cruise lines are starting offer stops in Cuba, it’s the least relevant island in the group for US incentive travel today. However, the other three are powerful players in the market. Montego Bay Jamaica and the dynamic duo of the Secrets Wild Orchid and the Secrets St. James continues to be client-favorite destinations for us. Convenient travel options make a 3 or 4-night program easy to execute. The All-Inclusive options are plenty in the Dominican, with multiple properties from the Secrets brand, two Paradisus options, Hard Rock, and many more. For Puerto Rico, the Ritz Reserve Dorado Beach continues to delight even the most well-traveled trip attendees!


There are many more islands included in the Lesser Antilles. To complicate it a bit more, they are further broken into two groups, Leeward Islands (northwestern islands, away from the wind “lee”) and Windward Islands (southeastern islands, exposed to the wind).

Leeward Islands

  • The Virgin Islands (US and British) – Stay tuned, we’ll dive into this region in a later installment
  • Antigua
  • Barbuda
  • Anguilla – the beautiful Four Seasons is sure to make a
    guest appearance in a future post
  • Saint Barthélemy
  • Saint Kitts – take a look at what’s happening with the
    Park Hyatt Christophe Harbour
  • Nevis
  • Montserrat
  • Guadeloupe
  • Dominica

Dutch/Netherland Antilles  – A subset of the
Leeward Lower Antilles

  • Saint Martin (Guadeloupe in the north and Netherlands Antilles
    in the south)
  • Saba
  • Sint Eustatius

In addition to the above, Aruba, Bonaire, and Curacao are often included in the Dutch Leeward Lesser Antilles category

Windward Islands

  • Martinique
  • St. Lucia
  • St. Vincent
  • The Grenadines
  • Barbados – stay tuned for more on Barbados offerings for your incentive program attendees
  • Grenada
  • Trinidad
  • Tobago

Lucayan Archipelago

The third, and easiest piece of the West Indies puzzle is the Lucayan Archipelago, which is simply comprised of the Bahamas and the Turks and Caicos. Easy, right?

The Caribbean consists of more than 700 islands, islets, reefs, and cays. The entire region is a favorite in the incentive travel industry, and a little bit of insight can go a long way in planning a meeting or event.

So now that we’ve established what/where we are talking about, I look forward to sharing more insights throughout this series. I will start in the West Indies, with a Leeward Lower Antilles island. That should narrow it down for you at least a little!

Julie Blank

Author Julie Blank

Director, Strategic Accounts | Expertise is pushing for excellence and making our services and deliverables as good as they can possibly be.

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