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I don’t know about you, but there are few better ways to incentivize me to perform than with the promise of a trip to an exotic Caribbean island. From the year-round sunshine and crystal blue waters to the lively calypso music and tropical cuisine, the Caribbean is quite literally paradise on earth. But which destination is the best fit for your team?

In this incentive travel guide to the Caribbean, our group travel experts are breaking down their top picks for group incentive travel and where to stay at each of them. Pack your bags and get ready to give your top performers the trip of a lifetime!

Overview of the Caribbean

Before you can decide which Caribbean island works best for you and your team, you should probably learn a little bit about the region as a whole. Located southeast of the Gulf of Mexico, the Caribbean region is made up of the Caribbean Sea and the hundreds of islands that span across it.

The island group, or archipelago, itself is actually referred to as the West Indies. This group can be further broken down into the Greater Antilles, Lesser Antilles, and Lucayan Archipelago. Between these entities, there are over 700 islands.

Image of Aurora Anguilla Resort & Golf Club by Aurora Anguilla Resort & Golf Club

Image of Malliouhana Resort by Auberge Resorts Collection

Anguilla – Paradise for Small Groups

If you’re traveling with a smaller group (think 25 rooms or less), then Anguilla incentive travel is a spectacular choice. This picturesque island is a British territory in the Lesser Antilles featuring 16 miles of white-sand beach and a wide array of exciting things to do.

While Anguilla is flush with first-class accommodations and outdoor activities, it’s also free from crowds and cruise ships—a huge added bonus. Stunning hotels like the Four Seasons Resort Anguilla, Aurora Anguilla Resort & Golf Club, and Malliouhana Resort are dripping in the kind of luxury you might not expect from a developing island. While Anguilla doesn’t yet have many options for larger groups, it’s the ideal spot for smaller ones.

Image of Grand Hyatt Baha Mar by Grand Hyatt Baha Mar 

Image of Rosewood Baha Mar by Rosewood Baha Mar 

The Bahamas – Tourist Treasure Trove

The Bahamas is a sovereign country in the Lucayan Archipelago made up of 16 islands. Between the striking blue waters, booming nightlife, and incredible natural beauty, the Bahamas maintains a spot as one of the Caribbean’s most popular destinations for all types of travelers. While this is definitely one of the more crowded picks on this list, Bahamas incentive travel is fantastic for those looking for a lively trip with lots to do.

For a luxurious beachfront stay, it doesn’t get much better than the Grand Hyatt Baha Mar or Rosewood Baha Mar. If you want to enjoy the dining and entertainment options of the iconic Atlantis Resort but want a more upscale stay, The Cove at Atlantis offers both. We also can’t forget about SLS Baha Mar, a resort-style hotel designed to serve as a tropical sanctuary for its guests.

Image of Hyatt Zilara Cap Cana by Playa Resorts

Image of Paradisus Palma Real Golf & Spa Resort by Meliá Hotels International

The Dominican Republic – Large Group Pick

Located just two hours from Miami by plane, the Dominican Republic is one of the Caribbean’s most popular and culturally diverse islands. It’s also the second-largest island of the Greater Antilles chain. The Dominican Republic is known for its huge selection of beachfront resorts, rich culture, friendly locals, and stunning landscapes.

In addition to being a favorite among leisure travelers, the Dominican Republic is also a favorite for incentive trip planners. We love all-inclusive jaw-droppers like the Hyatt Ziva & Zilara Cap Cana, Live Aqua Beach Resort Punta Cana, and Paradisus Palma Real (great for golfers!). If you have an affinity for insanely opulent pools, these hotels do not disappoint.

Image of The Westin Grand Cayman Seven Mile Beach Resort & Spa by The Westin Grand Cayman Seven Mile Beach Resort & Spa

Image of The Ritz-Carlton Grand Cayman by Marriott International Hotels

Grand Cayman – The Best of Both Worlds

If you’re looking for Caribbean incentive travel that offers an eclectic combination of water activities by day and ritzy oceanfront dining by night, look no further than Grand Cayman. The largest of the Cayman Islands, a British territory in the Greater Antilles, this group incentive travel hotspot truly has it all.

Grand Cayman stands out for being significantly more developed than other islands in the region, with an impressive collection of high-end resorts for groups like The Ritz-Carlton, Grand Cayman and Kimpton Seafire Resort + Spa. If ocean-view resorts with swim-up bars are your thing, then The Westin Grand Cayman Seven Mile Beach Resort & Spa is not to be missed.

Image of Hyatt Ziva Rose Hall by Playa Resorts

Image of Secrets St. James & Wild Orchid by AMResorts

Jamaica – Cultural Hub of the Caribbean

If it’s the culture you’re seeking, Jamaica is the place to be. Known as the Caribbean’s cultural hub, Jamaica is home to an electric array of live reggae music, street performances, and festivals. In addition to the thriving cultural scene, Jamaica features an incredibly diverse (and mind-numbingly beautiful) landscape.

Here you can find lush rainforests, staggering mountains, and some of the world’s most beautiful beaches. Treat your top performers to one of the many all-inclusive resorts, like the Hyatt Ziva Rose Hall or Secrets St. James & Wild Orchid. For something smaller and more luxurious, try the Half Moon or Round Hill Hotel and Villas.

Image of Condado Vanderbilt Hotel by Preferred Hotels

Image of Dorado Beach, a Ritz-Carlton Reserve by Marriott International Hotels

Puerto Rico – The Underrated Gem

I’m willing to bet that Puerto Rico doesn’t jump to the front of your mind when you think of Caribbean incentive travel. This paradisiacal island is rich in cultural history and bursting with breathtaking natural beauty everywhere you turn. Not only that, but it’s a US territory (which makes for easier traveling) and is located just 3 hours from Miami.

The people are warm and welcoming, the landscapes are vibrant and diverse, and the resorts are way more glamorous than most people realize. I bet you didn’t know there was a AAA Five Diamond Resort in Puerto Rico! (Ahem, The St. Regis Bahia Beach Resort). For a Puerto Rico incentive travel experience that your team will never forget, check out the ultra-lux Dorado Beach, a Ritz-Carlton Reserve, or the enchanting Condado Vanderbilt Hotel.

Mark our words – Puerto Rico is making a comeback!

Image of Park Hyatt St. Kitts Christophe Harbour Hotel by Park Hyatt St. Kitts Christophe Harbour Hotel

Image of Four Seasons Nevis by Four Seasons Nevis

St. Kitts and Nevis – Island Hopping Heaven

While St. Kitts and Nevis are two separate islands, together, they make up a dual-island nation situated around 27 km from one another. Both of these Caribbean islands have plenty to offer to those looking for premier group incentive travel, from authentic Caribbean cuisine to immaculate 5-star resorts.

If you want to do a little bit of easy island hopping, I highly recommend planning your incentive trip in St. Kitts or Nevis. You can get from one island to the other in under 30 minutes by taxi and car ferry. Take in the panoramic Caribbean Sea views from the Park Hyatt St. Kitts or enjoy a more secluded getaway from the serene Four Seasons Nevis.

Image of Sugar Beach, A Viceroy Resort by Viceroy Hotel Group

Image of Royalton Saint Lucia by Blue Diamond Hotels and Resorts Inc.

St. Lucia – The Newcomer in Luxury

In recent years, St. Lucia has been rising in popularity as an incentive travel destination. Between the dramatic scenery, year-round warm weather, and vast collection of luxury resorts, it’s not hard to see why. This magical island is located in the Lesser Antilles and spans 27 miles of lush rainforests and pristine beaches.

St. Lucia incentive travel offers the perfect combination of relaxation and excitement, where you can enjoy everything from yoga on the beach to ziplining through the jungle. For breathtaking views of the Pitons and luxurious amenities like butler service, Sugar Beach, a Viceroy Resort is a must for group incentive travel. Other fantastic options include the all-inclusive Royalton Saint Lucia and the dazzling Marigot Bay Resort.

Image of The Ritz-Carlton, St. Thomas Resort by Marriott International Hotels

Image of The Westin Beach Resort at Frenchman’s Reef by Aimbridge Hospitality

St. Thomas – Tropical Playground Without a Passport

If you’re looking to treat your top-performing superstars to a Caribbean incentive travel experience that doesn’t require a passport, look no further than St. Thomas. Those stunning clear turquoise waters will make you feel like you’re much further from home than you really are, and the upscale digs certainly don’t hurt either.

Beach bums and adventurers alike will fall equally in love with this enchanting island, where sun-drenched coastlines and panoramic mountain views are plentiful. Take your team snorkeling with sea turtles by day and dine out at the upscale casual restaurants by night. Newly-renovated The Ritz-Carlton, St. Thomas and Westin Beach Resort at Frenchman’s Reef are both amazing options for group incentive travel.

The Ritz-Carlton, Turks & Caicos Resort by The Ritz-Carlton, Turks & Caicos Resort

Image of The Palms Turks & Caicos by The Palms Turks & Caicos

Turks & Caicos – Caribbean’s Best-Kept Secret

A culmination of over 40 islands located south of the Bahamas in the Lucayan Archipelago, Turks & Caicos has been a longtime favorite among celebrities and the elite. While it was once considered to be the Caribbean’s best-kept secret, these enchanting islands are quickly becoming a popular choice for group incentive travel.

Turks & Caicos is home to the kind of pristine beaches you’ve only seen on a postcard, many of which have earned the islands countless awards and recognition. The Ritz-Carlton, Turks & Caicos offers lavish suites and sophisticated dining options, while The Palms Turks & Caicos is centered in the world-famous Grace Bay Beach with a bevy of luxury amenities. You really can’t go wrong here.

Premier Incentive Trip Planning Services

When it comes to planning incentive travel, we all want to treat our top performers to the best. There are many reasons why the Caribbean is one of the most popular travel destinations in the world, and we hope that this incentive travel guide to the Caribbean helped to solidify that for you.

Want some help planning your team’s next big trip? At Brightspot, we specialize in curating incentive travel experiences that create lifelong memories for our clients. Contact us today to speak with one of our travel experts about your next adventure.

Mike May

Author Mike May

Mike is a wearer of many hats. President of Brightspot, author of 12.5 Steps to a Perfect Incentive Program, past Chairman of the Incentive Research Foundation (IRF), and recognized as one of the Top 25 Most Influential People in the Incentive Industry. His expertise includes bucket-list incentive trips, motivational incentive program design, matching event goals with the perfect destination & hotel, cost savings strategies, global channel reward programs, and targeted communications. Mike maintains his certifications in many specialties including Certified Meeting Professional (CMP), Certified Incentive Travel Professional (CITP), and Incentive Professional (IP).

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