Top Corporate Incentive Destinations in the Caribbean

The Caribbean is a cultural melting pot that offers a wide range of options for corporate incentive events of every size, budget, and length of stay. Whether you are looking for 200+ rooms and a thriving nightlife or 15 rooms and a relaxing oasis, island options abound with beautiful beaches, delicious cuisine, and world class hotels and resorts. 

Castle has worked in many of these Caribbean destinations at a range of properties such as the Ritz-Carlton ArubaGrand Hyatt Baha MarLa SammanaFour Seasons Nevis and several others. Here are ten of our top choices:

A grassy area is pictured, with numerous palm trees and hammocks hung between the trees.
Photo by @cristofer on Unsplash


These incentive travel destinations are a safe bet for group reward travel with options for every employee demographic and budget.


Aruba boasts more sunny days per year than any other Caribbean Island, top-ranked beaches, and refreshing trade winds.

Explore natural parks and diverse ecosystems by land or sea. Recreational activities range from touring the desert on an ATV to snorkeling ocean shipwrecks. Aruba’s capital city, Oranjestad, features brightly colored buildings and Dutch colonial architecture of the 1800’s adapted to modern use as shopping centers, restaurants, and cafés. Multiple daily flights from most major US cities make Aruba extremely accessible for group incentive programs. 

The Bahamas

The Bahamas’ 700 islands dotted across the Atlantic Ocean and Caribbean Sea attract visitors from around the world. It is a picture-postcard destination with white-sand beaches and translucent turquoise waters.

Nassau, its capital, is a bustling metropolitan hub full of culture and modern amenities that blend big city lure with the ease of a tropical paradise. From watersports, beaches and pools to casinos, vibrant nightlife and dining options, Nassau is a great option for reward travel.

The Bahamas is a just a few hours flight from many US east coast cities making it an extremely desirable location for many of our clients. 

Dominican Republic

The Dominican Republic is known for its warm and hospitable people, astounding nature, intriguing history, and rich culture. Surrounded by the Atlantic Ocean on the north and the Caribbean Sea on the south, this tropical island paradise boasts 1,000 miles of coastline, 250 miles of the world’s top beaches, magnificent resorts and hotels, and a wide variety of recreation and entertainment options.

The Dominican Republic is also the #1 destination for golf in the Caribbean and Latin America. Groups can choose from 25 designer golf courses with lush green fairways that stretch along breathtaking coastlines and mountain backdrops. The Punta Cana region has a rich nightlife and party scene and La Samana is home to Los Haitises National Park, a fantastic location for nature lovers. Casa de Campo is one of our favorite resorts for a high-end, luxury experience.


Jamaica’s resort areas of Montego Bay and Negril attract most of the island’s tourism. While many resorts are all-inclusive and so nice that you may not want to leave, there are plenty of great activities to lure you off property—like rafting on the Martha Brae River or a taking a day trip to Dunn’s River Falls and Nine Mile, the birthplace of legendary musician Bob Marley.

Montego Bay, affectionately called “Mobay” is located on the northwest coast of Jamaica and is home to picturesque white sand beaches, turquoise waters, and miles of palm trees. The island is rich in culture through tradition, language, cuisine, music, and art. Flights from most major US cities are available multiple times per day, making the island incredibly accessible for shorter incentive programs. Half Moon Bay Jamaica is another favorite.

An image of small paddle boats on the shore of the beach and in the water, as the sun is setting.
Photo by @raecaspar on Unsplash

Puerto Rico

If you are a US citizen, you do not need a passport to visit Puerto Rico. This US territory is known for its pristine beaches, rich history, vibrant culture, and exotic rainforests.

Locals are known for being gracious hosts who love to share their traditions and customs with visitors, making Puerto Rico one of the friendliest destinations in the Caribbean. Spend a day exploring the forts, cathedrals, and churches fundamental to the island’s heritage in Old San Juan—or browse the downtown shops and markets. If your group is more adventurous, plan a hike through the El Yunque National Forest or a visit the Bioluminescent Bay.

An image of Old San Juan pictured on the left and the shore on the right.
Photo by @fotowei on Unsplash

St. Thomas

St. Thomas is home to Charlotte Amalie, capital of the U.S Virgin Islands—and heart of the Caribbean since colonial times. Historic buildings and forts from the 1600’s add a historic touch to a relaxed and culturally unique island paradise.

This tiny island packs a punch when it comes to entertainment and leisure. Guests can relax and enjoy shopping, sailing, snorkeling, and golfing—on island time, of course. Magen’s Bay, named Best Beach of the Caribbean 2021 by the Caribbean Journal, is a must stop for avid beachgoers.

For groups looking to experience a bit more seclusion and adventure, St. John is a quick ferry ride away. The island is three quarters national park, lightly inhabited, and surrounded by the most calm and colorful waters in the Caribbean.

An image where Charlotte Amalie  is pictured in the foreground and the ocean is pictured in the background.
Photo by @kklumb on Unsplash


If you are looking for something a little more exclusive for your group, these incentive travel destinations require a bit more logistical planning—and budget—but are well worth considering. 


Antigua, located just north of the equator, is home to warm steady winds, a complex coastline, and an unbroken wall of coral reef. The trade winds that once blew British soldiers safely to shore make Antigua a beautiful place to sail—and a popular yachting destination. English Harbour hosts the annual Antigua Sailing Week regatta and one of the largest Charter Yacht shows each December. This classic Caribbean Island boasts English roots with narrow roads, candy-colored villages, and interesting historic sites. Spend a day in a secluded cove, enjoy kitesurfing at Jabberwock beach, or tour the Antigua Distillery. Exclusive options abound for groups traveling to Antigua.

A picture of one of Antigua's shores as the sun sets on the left side.
Photo by @rickjam on Unsplash

St. Kitts & Nevis

The sister islands of St. Kitts & Nevis are separated by a shallow channel called The Narrows. One of the highlights of St. Kitts, the larger of the islands, is the dormant Mount Liamuiga volcano.

A short boat ride from St. Kitts is Nevis, a small island with much to explore. Nevis features one of the last remaining rainforests in the Caribbean and inhabits more monkeys than people. It has a step-back-in-time feel where friendly village people, pristine beaches, and an unhurried lifestyle add to its unique appeal.

Nevis attracts visitors who appreciate a quieter, finer quality of life. The Four Seasons Nevis is one of the more luxurious hotel options in the Caribbean.

An image of the ocean in the foreground with palm trees and a mountain in the background. The sun is setting behind the right side of the mountain.
Photo by @mprage on Unsplash

St. Lucia

St. Lucia is the second largest of the Windward Islands and boasts the finest mountain scenery in the West Indies. Known for its dramatically tapered Piton mountains, St. Lucia’s coastline is home to volcanic beaches, luxury resorts, and quaint fishing villages. This emerald isle remains unspoiled—a checkerboard of green-mantled mountains, valleys, and wild orchids. St, Lucia is known for its warm culture, lively nightlife, and infamous rum punch—a favorite stop-off for island-hoppers, yachters, and jetsetters alike. Two resorts we recommend are Jade Mountain and Sugar Beach.

St. Martin

The French and the Dutch have shared St. Martin in a spirit of neighborly cooperation for 350 years. The French side (St. Martin) exudes comfort and elegance with secluded beaches, luxury resorts, and lavish accommodations. The Dutch side (Sint Maarten) bustles with trade and tourism, busy cruise ports, and commercial districts.

The island’s picturesque white sand beaches and endless turquoise waters are home to an array of coral reefs and underwater caves filled with tropical fish. Dubbed the “gourmet capital of the Caribbean,” St. Martin offers hundreds of eateries from lolo’s—beach shacks—to fine dining. St. Martin is a tropical paradise and refuge for those seeking the beauty of the Caribbean with the elegance and culture of a European getaway.

No matter your budget, group size, or vision for your event, there is a location that is sure to offer your guests a trip of a lifetime. Castle’s Event Management team stays ahead of the trends and is always on the lookout for options that meet our client’s needs—in the Caribbean and all over in the world. We can help you make your reward program a success. Contact us to help you plan your incentive events or choose the right destination for your corporate incentive program.

The Castle Group, Senior Event Manager, Paige Myers
Written By: Paige Myers


Outdoors of the Castle Group office