El Morro National Monument in San Juan, Puerto Rico. The U.S. Territory offers the cultural experiences of the Caribbean, but without needing a passport. Courtesy of Discover Puerto Rico

When the snow starts and the temperatures plunge, many planners’ thoughts turn to warmer locales for meetings and events. That’s where the islands of the Caribbean and the Bahamas come into play. From cultural and environmental diversity, spectacular beaches, mountains and tropical forests, to proximity and direct access to two continents, the islands of the Caribbean and the Bahamas are an ideal meeting spot for any size group.

As Bethanie DeRose, CDME, senior vice president, tourism and destination advisory practice with JLL’s Hotels and Hospitality Group explains, “The notion of being able to escape and enjoy some leisure time while traveling for work meetings makes the Caribbean timelessly attractive.”

Attendees want a more immersive experience, and the Caribbean is a great place to enable that. “Any off-sites that can be activated for team events or opportunities to have experiences should be considered,” DeRose says. “Of course, the efficiency of arrival and departure are important, so the planner’s ability to work with destination partners to streamline that experience is a big plus.”

The meeting planning team at Brightspot recently sourced, planned and managed a client’s elite club trip to the Caribbean, specifically Grand Cayman, for their direct and indirect channel teams. “Our team and the client’s planning team came in, along with client hosts, a few days before the direct winners arrived for a three-night program,” says Michael Butler, vice president of sales at Brightspot. “Following their program, the top channel partners came in for a second wave, with hosts staying the full week. The Caribbean fares well post-pandemic because it’s closer to home for U.S.-outbound programs.”

The country of St. Kitts & Nevis offers activities unique to each island, which are 2-1/2 miles apart. Courtesy of St. Kitts Tourism

St. Kitts & Nevis

An unspoiled and lush historic pair of islands in the Caribbean, St. Kitts & Nevis, can be accessed by direct flight from many North American cities. This getaway is an instant paradise. Expansive function space, on- and off-site activities — from golf to sailing to monkey-watching — and luxe accommodations, make Four Seasons Resort Nevis an ideal choice for meetings, events and incentive travel. “An incentive trip to Four Seasons Resort Nevis is unforgettable,” says Terrance Kelly, director of sales at Four Seasons Resort Nevis. “With luxurious accommodations, including more than 50 private villas, our own golf course, delicious Caribbean cuisine and exciting recreational opportunities, your top employees will leave here feeling pampered and rewarded.”

Planners can stage a formal affair in the ballroom, which can accommodate as many as 300 attendees, or opt for one of the resort’s smaller salons for a more intimate event. “If you prefer the outdoors, we deliver function lawns, gardens and our popular South Beach venue. It’s directly on the Caribbean, where our artists can create a sand sculpture to fit your theme,” Kelly says. “The small island requires that we order and import things, so you need to order in advance. There are no street lights, [and] there are monkey and donkey crossings, so give a little extra time while planning off-site dinners.”

Cinthya Cabrera, meeting planner and general manager at Sunlinc, created a farewell gala dinner on South Beach at the Four Seasons Resort Nevis. “The blank canvas of the beach alongside the backdrop of Nevis Peak and the Caribbean Sea was absolutely perfect for a really special evening,” Cabrera says. “We were able to customize the infrastructure to match the vision of the event in this magnificent space. The Four Seasons Resort Nevis is authentic Caribbean luxury with traditional plantation-style accents with a perfectly modern twist. This stunning resort is fully committed to the highest standard of quality and service, offering a sense of place at this unique secluded destination.”

Cabrera adds that if your incentive trip requires a high-end secluded Caribbean experience, she highly recommends considering St. Kitts & Nevis. “While sometimes clients are concerned that there will not be enough to do on a small Caribbean island, this, in fact, is far from the reality. Unlike other islands in the Caribbean, St. Kitts & Nevis are one country, featuring two islands, where there is no passport control, no borders and no immigration between them,” Cabrera says. “Since the islands are 2-1/2 miles apart, the ability to offer attendees two totally unique islands during a multi-day program really does set this destination apart from all others.”

There also is an abundance of activities between the two islands. Attendees can enjoy rainforest hiking tours, sunset horseback riding, customized rum and plantation tours, biking tours, zip lining, 4×4 off-road tours, a double story scenic train that runs on tracks built more than a century ago, plenty of water sports and more.

The Ritz-Carlton, St. Thomas offers more than 10,000 sf of indoor and outdoor meetings and events space, seven outdoor function venues, including two ocean view gazebos, and five indoor meeting rooms.

U.S. Virgin Islands

Considered to be the classic Caribbean experience, the U.S. Virgin Islands are ideal backdrops for meeting and incentive events. Set amidst breathtaking natural beauty, nestled between Great Bay and a green mountainous skyline, The Ritz-Carlton, St. Thomas features an alluring blend of sea-inspired luxury amenities and a new Caribbean-inspired design. The resort reopened its doors in 2019, following a period of extensive enhancements. The all-encompassing, $100 million project includes fully redesigned public spaces, rooms and suites, events and meetings spaces, and dining venues. The reimagined resort brings the beauty of the U.S Virgin Islands to life, enticing business and leisure travelers to fall in love with the property and the destination all over again.

Lauren Cramer, chief event planner at Turn-Key Events, orchestrated an annual incentive trip for Rapid7 at The Ritz-Carlton, St. Thomas. “Our attendees are looking for warm weather with lots of activities. As planners, we were looking for a high level of service that could carry out the vision that we had. The Ritz-Carlton, St. Thomas went beyond our expectations,” Cramer says. “At every step, they offered creative solutions and were committed to executing a flawless event for us. After our initial site visit, we knew we partnered with the right hotel to create an outstanding experience.”

The Ritz-Carlton, St. Thomas features more than 10,000 sf of indoor and outdoor meetings and events space, seven outdoor function venues, including two ocean view gazebos, and five indoor meeting rooms totaling 5,141 sf with ample pre-function areas. Its exquisite Great Bay Ballroom offers high ceilings and floor-to-ceiling windows, state-of-the-art A/V equipment and technicians, and private dining at Oasis at Bleuwater, which accommodates up to 50 attendees.

Cayman Islands

“Beyond the perfect weather and crystal blue waters, sourcing an incentive trip to the Caribbean offers your attendees a unique experience of diversity, gorgeous scenery and incredible cuisine,” says Kelly Hamlet, director of catering and events at Kimpton Seafire Resort + Spa. Located on Grand Cayman, Kimpton Seafire Resort + Spa is the boutique hotel company’s first international luxury resort, delivering an unforgettable island escape. Seafire opened its doors in November 2016, offering contemporary architecture that unfolds dramatically to the grounds, the beach and the sea. Kimpton Seafire’s meetings and events spaces amplify the setting, with eclectic and inspiring interiors, and ample opportunities for indoor/outdoor activities. The hotel offers 13,630 sf of indoor meetings and events space, and 9,350 sf of thoughtfully designed outdoor function space offering ideal venues for Caribbean-crafted weddings, social celebrations, incentive group events and corporate meetings.

“Few destinations offer such a variety of water sports options for all experience levels, incredible range of regional cuisines with the freshest seafood, unique and beautiful cultural customs, along with the highest level of luxury service,” Hamlet says. “Make sure to include a sunset catamaran trip for all of your incentive groups. This is a team-bonding experience that will be remembered fondly by all.”

The Turks & Caicos islands, which offer world-renowned diving, are 30 miles southeast of the Bahamas and 90 minutes from Miami by air. Courtesy of the Turks & Caicos Tourist Board

Turks & Caicos

From executive retreats and small corporate meetings to once-in-a-lifetime incentive programs, Beach Enclave Turks & Caicos can accommodate groups of up to 90 attendees. Planners can choose from 27 private, luxuriously appointed villas located in three distinctive, beachfront communities. For memorable dining, a variety of themed catering menus are available, or groups can have their menus customized to their tastes and preferences by their personal in-villa chef. Pop-up dining experiences bringing in the flavors of local restaurants are also available upon request.

Located on the southeastern edge of Providenciales, Beach Enclave Long Bay is a dream-come-true incentive destination. This stunning, white-sand beach stretches more than 3 miles and ranks among the top 10 beaches in the world year after year. Groups can enjoy ideal conditions for water sports or even take on a new adventure, such as kiteboarding.

Rising 40 feet above the ocean on the island’s more remote northern shore, Beach Enclave North Shore features dramatic, elevated views of Turks & Caicos’ world-famous turquoise waters. Set within 10 acres of indigenous landscape, this location is ideal for groups seeking the utmost privacy and exclusivity.

Beach Enclave’s third and newest location, Beach Enclave Grace Bay, is situated just steps from the island’s best restaurants, shopping and nightlife. For groups seeking rejuvenation after a day, or night, full of play, wellness classes by Beach Enclave’s resident yoga instructors are available. Each small group session takes place on an open-air, ocean-facing deck. Options include yoga, meditation, intention setting and gratitude journaling, to name a few.

“Undoubtedly, the biggest draw of hosting a program in the Caribbean is the inspiring, picture-perfect setting. Turks & Caicos is blessed by Mother Nature with spectacular beaches and superb weather year-round,” says Keyona Coward, director of sales at Beach Enclave. “The villas at Beach Enclave are designed to bring the beauty of the outdoors in with floor-to-ceiling sliding glass doors, expansive terraces and exclusive access to a private beach, ensuring a captive and engaged audience.”

Anguilla

Melanie Sell, meeting planner and senior program manager at First Incentive Travel, recently orchestrated an incentive trip to Zemi Beach House in Anguilla, a small boutique resort ideal for the demands of small incentive corporate groups or general buyouts of around 150 people amidst a collection of 76 rooms. “We have an original and laid back — but exquisite — approach to our meetings and events,” says Antoine Alsayah, director of sales & marketing at Zemi Beach House. “You will not find banquet halls in paradise.”

The event Sell planned rewarded top dealers of a company’s brand. The attendees were leadership level individuals, such as CEOs and company owners. “This group consisted of 135 people total. The program was very detailed and had many moving parts, from speedboat transfers from Saint-Martin, small group excursions on Anguilla and Saint-Martin, to full group excursions, including a one-day buyout of a small island with catamaran transfers,” Sell says. “[Other activities included] an upscale awards presentation night, on-site live gifting experiences with the addition of room drop items each night, local entertainment, local photographers, themed and coordinated décor for on-site and off-site dinners, and events and fun after-dinner parties.” She adds, “This client strives to create a better program than the previous year. While some elements may seem over the top to some, they have become an expectation of sorts for these attendees. They look forward to being spoiled for their hard work year after year — and rightly so.”

The staff at Zemi Beach House are experts at utilizing event-appropriate inventive spaces, such as the resort’s gorgeously appointed spacious suites with oceanfront views, the beautiful Rum Room or directly on the beach on Shoal Bay, considered one of the most beautiful coastlines in the world. “The island is off the beaten path, quiet, laid-back, authentic and secluded,” Sell says. “It’s a perfect fit for a hideaway or an intimate gathering, with lots of privacy, making it a celebrity favorite, and for those looking to just get away and relax away from the crowds.”

Brad Dean, CEO of Discover Puerto Rico, standing, says the island is working to further develop it’s hotels, activities and attractions. Courtesy of Discover Puerto Rico

Puerto Rico

Considered one of the most beautiful, culturally diverse and accessible islands in the Caribbean, Puerto Rico — a U.S. territory — is a sunburst of tropical indulgences. Puerto Rico is known for its beaches, unique attractions and adventures. A business trip to the island would not be complete without some time set aside to explore Puerto Rico’s culture.

According to Brad Dean, CEO, Discover Puerto Rico, the island is undergoing developments to bolster its current lodging inventory of more than 163 hotel options, with nearly 14,500 hotel rooms open and operating. Most recently, Puerto Rico opened DISTRITO T-Mobile, a world-class, 5-acre experiential complex combining the best in global retail, destination dining with 12 gastronomic concepts, art, entertainment, music, technology and hospitality. It’s conveniently located in the Puerto Rico Convention Center District, just 6 miles from San Juan International Airport and alongside several hotels. This complex is destined to be the ideal option for events, conventions and performances, offering a multi-sensory, audiovisual and technologically advanced experience.

“We understand our meeting planners’ needs, especially with the latest evolutions of the industry, and our industry partners have adapted to the movement in offering both visual and hybrid options in the space,” Dean says. “The Puerto Rico Convention Center has an in-house broadcast studio, where hybrid meetings can be broadcast to virtual attendees with a plug-and-play concept for ease of use. Despite the pandemic, this time has brought us an opportunity to rethink how tourism interacts with our economy, society, resources and infrastructure.”

As Louise Bang, regional vice president, sales and distribution at Marriott International, Caribbean & Latin America, explains, Puerto Rico offers the perfect balance between business and pleasure. Here you’ll find the ease of doing business in a U.S. market along with the beauty and climate of a Caribbean destination. “There’s no passport required for U.S. citizens, the dollar is the island’s currency, and English is widely spoken throughout the island. Plus, you’ll find convenient airlift travel options to the island, including a variety of daily air service from cities throughout the U.S., and fully vaccinated passengers on domestic flights no longer need a negative COVID-19 test to enter Puerto Rico,” Bang says.

Marriott International boasts a variety of lodging options on the island, from first-class business hotels in urban tourist areas, such as the Sheraton Puerto Rico Hotel & Casino, to high-end tailored gatherings and buyouts ideal for group meetings, incentive trips and executive retreats at Dorado Beach, a Ritz-Carlton Reserve. “And with plenty of outdoor attractions to choose from, attendees will create unforgettable memories while hiking to [everything from] tropical rainforests to waterfalls; exploring Old San Juan, a UNESCO World Heritage Site; enjoying its enticing gastronomy; or simply meeting its people, who are charismatic, hospitable and passionate,” Bang says.

In terms of the ultimate venues, San Juan’s new premier entertainment hub has something for everyone. If you’re looking for a place that has it all, the DISTRITO T-Mobile should be on any meeting planner’s radar. This trendy spot is ideal for experiencing Puerto Rican art, flavors, rum culture, music, dance, adventure and overall vibrancy. For large-scale events, the Puerto Rico Convention Center has more than 500,000 sf of versatile meeting space and the most technologically advanced A/V capabilities in the region.

The firm Serra & Serra Group, which specializes in continuing medical education events, has coordinated several events at the Caribe Hilton hotel in San Juan. One of the most outstanding was the XXIX Annual Congress of the Ibero-Latin American Society of Diagnostic and Therapeutic Neuroradiology. This event was attended by about 400 people from various countries in Latin America, Europe, and the United States.

Caribe Hilton offers a series of attributes that make any event memorable. It has spacious and comfortable meeting rooms, ideal for all types of activities, as well as spectacular exteriors. Specifically, the property features more than 65,000 sf of versatile meeting space, which incorporates three ballrooms and plenty of picturesque outdoor event spaces, inclusive of the resort’s beach, sprawling oceanfront pool area, sweeping gardens, a gazebo, terraces and more. In addition to plenty of outdoor space, the hotel provides groups with the option to keep accommodations within one building or wing of the hotel. “For our event, we sought a hotel that also had a historical background representative of the island,” says Vionesse Serra, president of Serra & Serra Group. “The Caribe Hilton brand is synonymous with Puerto Rico, and we wanted our international guests to have a first-class Puerto Rican and Caribbean experience.”

Caribe Hilton’s meetings and events space is big enough to accommodate convention-sized groups, yet the property offers a true leisure feel so groups get the best of both worlds and enjoy San Juan in style. “We offer a variety of on-site amenities for groups, including a secluded beach, oceanfront swimming pools, snorkeling and ‘snuba’ diving, tennis clinics at the Monica Puig tennis center, piña colada demos, revitalizing spa services and more,” says Letty Rivero, director of sales and marketing at Caribe Hilton.

When they’re not soaking up the sun or learning to blend the perfect cocktail, attendees have easy access to the area’s hottest restaurants and bars, rainforest excursions, local food and rum tours, and additional activities that showcase the island’s rich culture.

Atlantis, Paradise Island in the Bahamas offers more than 200,000 sf of indoor meetings and events space.

The Bahamas

With more than 700 islands and cays, and 16 unique island destinations, The Bahamas lies just 55 miles off the coast of Florida, offering an easy fly-away escape. There is world-class fishing, diving, boating and thousands of miles of spectacular water and beaches. Nassau is the tourism hub of the island chain, boasting luxurious resorts, casinos, dining, shopping and a vibrant nightlife — in other words, there are plenty of activities for attendees.

The largest and most popular resorts on Nassau include Atlantis, Paradise Island and Baha Mar. Atlantis offers five types of accommodations from which to choose: The Cove, The Royal, The Coral, The Beach and The Reef. There is more than 200,000 sf of indoor meetings and events space, including the Imperial Ballroom, which, at 50,000 sf, can accommodate as many as 4,000 attendees. The 25,000-sf Grand Ballroom can accommodate groups of up to 2,700. There is 300,000 sf of outdoor meetings and events space, including the Royal Deck and Cove Beach.

Baha Mar is home to three uniquely designed resorts with amenities that include the Caribbean’s largest casino, at 100,000 sf. There is also a 30,000-sf spa, a convention center and more than 40 restaurants, bars and lounges. Grand Hyatt Baha Mar offers 1,800 guest rooms and suites; SLS Baha Mar offers 300 rooms, including 107 residences; and Rosewood Baha Mar offers 185 oceanview rooms and suites, and five beachfront villas. Baha Mar’s Performing Arts and Convention Center, which doubles as an art gallery, offers 200,000 sf of state-of-the-art indoor and outdoor spaces.

Tips For the Caribbean

When orchestrating an event in the Caribbean, Hamlet says it’s important to remember that “island time” is a real thing. “Always remember to adapt as best [as you can] to the local culture, especially when on-site, as the local staff and vendors may be more relaxed than you are used to in city destinations,” Hamlet says. “A big smile goes a long way, as islanders place a great importance on hospitality and kindness.”

Also, book your vendors further in advance than when working domestic programs, especially on smaller Caribbean islands or during peak group season from February to May. Hamlet adds that the benefit of traveling to the Caribbean region is that there are so many cultural experiences for your attendees to engage in during their trip. “An immersive Caribbean cultural event can be a life-changing moment for guests new to the region, so make sure to include a touch of the island when planning your welcome reception entertainment,” Hamlet says. “Seek local vendors to enhance your group events, from basket weavers to local cigar rollers, to indigenous musicians, all the while supporting the local economy.”

Peter Lombard, meeting planner and founder/CEO of Globe Guides, a company focused on helping companies around the world plan staff retreats, incentive trips, leadership retreats and events, recommends getting off property for at least some of the meals, as there are so many great restaurants across the region that give such varied angles on culture, food and the people that it really steps up the experience. “Also, let people come in and unwind the rest of the day. This kills two birds with one stone, any flight delays will not impact the program, and everyone is in a rested and excited state of mind for the full event,” Lombard says. “And be sure to look at what the region has beyond the property. More and more travelers are wanting an immersive experience, not just a vacation. This means that while the hotel is very important, it cannot stand alone; there have to be local restaurants, activities [and] local guides to complete the experience that a growing number of today’s travelers expect.”   C&IT