If you’ve been tasked with planning your organization’s President’s Club trip, you’re probably feeling a lot of pressure right about now. What location will inspire and motivate your team members to perform at their highest levels? In our experience, the promise of a trip to an idyllic Caribbean destination. There’s just something about crystal blue waters, swaying palm trees and mesmerizing calypso music that gets your top performers to outperform last year’s numbers!
For specific destination recommendations, see our 2027 President’s Club destinations guide.
Best Caribbean P-Club Trip Ideas for 2027
Anguilla
Just saying the name elicits calm and relaxation. Anguilla is a picture-postcard island and British territory in the Lesser Antilles. It boasts 16 miles of pristine white sand beaches and a plethora of cool things to do.
This is a great spot for your President’s Club trip for a couple of reasons: First, there are plenty of first-class accommodations and amenities to please your group. Second, you won’t get the crowds because there are no cruise ships that dock here. That is a BIG bonus.
Some of our favorite hotels on the island are the Four Seasons Resort Anguilla, Aurora Anguilla Resort & Golf Club, and Malliouhana Resort. All in all, this is an ideal spot, particularly for smaller groups.
The Dominican Republic
Located just 2 hours from Miami by plane, the Dominican Republic, or as it affectionately called by locals – DR, is one of the most culturally diverse islands in the Caribbean. Known for its luxury beachfront resorts and stunning landscapes, we love this destination because the locals are so friendly and there is such good food here!
It’s not a mistake that leisure travelers flock to DR each year and your team will be happy staying at any number of upscale resorts. Some favorites are the Hyatt Ziva & Zilara Cap Cana, Live Aqua Beach Resort Punta Cana, and Paradisus Palma Real.
Grand Cayman
We love sending President’s Club teams to the Grand Cayman because it offers the best of both worlds: a calm slice of paradise and ritzy nightlife. The largest of the Cayman Islands, this destination has it all when it comes to hotel options, fine dining, shopping and nightlife. Some of our favorite resorts on the island are The Ritz-Carlton, Grand Cayman and Kimpton Seafire Resort + Spa.
St. Kitts and Nevis
Talk about island hopping Heaven! These two islands have plenty to offer incentive groups, from 5-star luxury beachfront resorts to mouthwatering authentic Caribbean cuisine. These two islands also offer an abundance of peace and quiet, and some of the most crystal water we’ve ever seen. Your team members can get from one island to the other in under 30 minutes by taxi or car ferry, so you can plan meetings and events easily. For luxury accommodations, check out the Park Hyatt St. Kitts. If your group would benefit from a more secluded getaway, check out the serene Four Seasons Nevis.
St. Thomas
Where do you send your top performers if not all of them have a passport? St. Thomas!
This tropical playground boasts stunning clear turquoise water, powdery soft sand beaches and luxury accommodations that will make your team believe Heaven on Earth exists.
There is so much to do on this island. We recommend taking your team snorkeling with sea turtles, it is an incredibly memorable experience. At night, treat them to dinner at an upscale restaurant. For resorts we suggest the newly-renovated The Ritz-Carlton, St. Thomas and Westin Beach Resort at Frenchman’s Reef.
St. Lucia
A relative newcomer to incentive travel destinations, St. Lucia offers dreamy scenery and numerous luxury resorts sure to please. The only thing that beats the pristine beaches is the lush rainforest that sits alongside it. Magic is what this tiny island offers.
This is an ideal destination for those groups who are looking for the perfect combination of R&R and adventure. For those on your team who want to do very little, they can enjoy yoga on the beach and then sip a freshly made fruit smoothie. For those adrenaline junkies, have them zipline through the jungle. Luxury accommodations abound and we recommend Sugar Beach, a Viceroy Resort (they offer butler service). Other great options for all-inclusive resorts are the Royalton Saint Lucia and the dazzling Marigot Bay Resort.
The Wrap
As event planners, we want to do our very best to treat our top performers to a memorable and luxurious experience. And you can easily do that by sending them to any one of these Caribbean destinations.
If you need any help planning your team’s next President’s Club trip, get in touch with us. We specialize in creating incentive travel experiences that are truly memorable.
Related reading: 5 Domestic Incentive Travel Destinations
Related reading: Top International Incentive Travel Destinations
Related reading: 2027 President’s Club destination guide
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