Sun, Sand and SplendorOctober 1, 2025

Caribbean & The Bahamas By
October 1, 2025

Sun, Sand and Splendor

Caribbean & The Bahamas
Eagle Beach, Aruba

Eagle Beach, Aruba

Shifting away from the traditional locales that are ideal for financial and insurance meetings and events can boost employee morale, increase productivity and improve team collaboration. Unlike traditional conference and meeting venues, the Caribbean and Bahamas offer a setting that allows attendees to disconnect from daily routines and explore the beauty of the tropics. In addition, many resorts are designed for large groups, with all-inclusive amenities that help streamline costs and logistics.

Sacha Walton, CEO and event producer for SWI Management Group, is currently planning the “Biz Her Way Power Summit” in Punta Cana, Dominican Republic next March and The Digital Nomad Summit in August. She also provided event assistance to an event in Juan Dolio, Dominican Republic in May of this year.

“There is an increase of international corporate events taking place annually,” says Walton, who is drawn to the Caribbean because of the region’s reasonable flight times, all-inclusive resorts and relaxing vibes for the mental escape.

“Who doesn’t like sipping Mai Tais by the beach after a day of workshops?” Walton says.

The Dominican Republic was Walton’s choice because of the easy airline routes, the reasonable cost of airfare, and she’s very familiar with the country.

“Their increase of economic growth is another driving factor, as well as the many expat entrepreneurs we can market the event to,” Walton says. “Punta Cana is also very accommodating to American culture and is easy to navigate without many language barriers, and many event resources are there to avoid shipping supplies.”

Walton also loves the partnership she’s established as part of the event with a local women’s shelter where they can make a donation, which supported the group’s social responsibility efforts.

“My advice to other planners considering planning events in the Caribbean is to research the area, select an all-inclusive resort to minimize costs, ensure there is airport transportation available, plan time for attendees to enjoy the resort, and create an immersive experience,” Walton says. “Be prepared for deposits. Many hotels and resorts in the U.S. offer direct billing and it’s not widely offered in the Caribbean. Also, when selecting a Spanish-speaking country within the Caribbean, have someone on your planning team who speaks Spanish or select a major brand resort where many are bilingual.”

Michelle Crosby, CMP, CITP, account executive at Brightspot Incentives & Events, recently planned an annual 150-person business kickoff meeting that is held each spring at a different resort location in the Caribbean.

“This two-and-a-half day program brings together various business units, executive leadership and the top 25 sales performers,” Crosby says. “Together, they share ideas, learn new techniques, network and recognize milestone achievements.”

For Crosby and the attendees, the Caribbean allows the group to focus on both business but also culture. As the Caribbean is part of this client’s portfolio, hosting a program in the islands provides colleagues from other parts of the world an opportunity to get to know some of their colleagues better.

“Plus, a resort located near the water with a smooth beach and accessible marina allows for the implementation of rest and rejuvenation in between stressful meeting agendas,” Crosby says.

The Caribbean Islands are more than just fun in the sun. As Crosby explains, they are a wonderful way to infuse a bit of wellness and recognition into a standard hum-drum annual sales meeting.

“While many hotels are designed with the leisure traveler in mind, many have conference centers and unconventional event locations that can help spur out-of-the-box conversations and perhaps some fresh new perspectives and ideas,” Crosby says. “A site visit is always encouraged to ensure that the resort has the necessary onsite catering and event services team that will compliment your event.”

Recently, Jeffrey Hensel, broker associate with North Coast Financial, which is a real estate short-term, asset backed lending company based in California, helped plan a leadership retreat of a company of investors and real estate professionals in the Caribbean where the venue in itself became a viable option in terms of ambience and availability.

The Caribbean, he says, offers easy airlift, good hospitality and great resorts. “I make it a practice to incorporate a relaxed atmosphere with discussions geared around finance as it makes the participants open up and build stronger relationships in longer term alliances,” Hensel says.

He advises planners to assess the cost-to-travel convenience ratio and the capability that the venue has to accommodate formal meetings with some that are less formal.

“The Caribbean is outstanding in terms of balance, and that is the reason why it still attracts groups of professionals who care about not only productivity but building relationships as well,” Hensel says.

When not in meetings, attendees at Atlantis Paradise Island can hit the links at the Ocean Club’s 18-hole par 72 championship course.

When not in meetings, attendees at Atlantis Paradise Island can hit the links at the Ocean Club’s 18-hole par 72 championship course.

The Bahamas

Atlantis Paradise Island recently underwent a $150 million resort-wide transformation and introduced new luxury retail and food and beverage openings as well as a reimagined casino. In addition, the resort’s new state-of-the-art pickleball courts are a popular option for attendees looking to relax and unwind after a day of meetings. The resort’s redesigned Atlantis Casino includes the Bar Sol cocktail lounge and a redone Moon Bar overlooking the casino floor.

Atlantis Paradise Island features over 500,000 sf of indoor and outdoor flexible meeting space with state-of-the-art technology, plus an array of interactive experiences customizable for groups of all sizes.

In addition to a wealth of meeting venues throughout Atlantis, meeting planners who host an event there can help financial and insurance companies and their attendees make a meaningful impact. Atlantis supports World Central Kitchen (WCK) and its mission to use the power of food to nourish communities and strengthen economies in times of crisis and beyond. When a group selects the WCK banquet option, a donation is made in the organization’s name, with a matching contribution from Atlantis, helping to advance WCK’s humanitarian efforts.

In addition, booking a group event at Atlantis contributes to the protection of marine species in decline, with a donation made in the organization’s name to the Atlantis Blue Project Foundation. The foundation advances solutions for a variety of challenges, including coral reef and habitat conservation, as well as improving the health of marine life and the surrounding oceans.

Grand Hyatt Baha Mar is another gem in the Bahamas that has captured the attention of planners and attendees alike. Attendees can explore the Baha Bay Waterpark, which is complete with 24 waterslides, a floating river and wave pool. When it comes time to get down to business, groups can enjoy over 200,000 sf of indoor and outdoor event space, including the Baha Mar Convention, Arts & Entertainment Center. The picturesque beachside meeting areas and the expansive outdoor event lawn allow attendees to enjoy the tranquil setting while also engaging in the business activities at hand.

One of the many amenities at Atlantis Paradise Island is their casino, which offers 80 gaming tables, including Blackjack, Craps, Roulette, Baccarat and more.

One of the many amenities at Atlantis Paradise Island is their casino, which offers 80 gaming tables, including Blackjack, Craps, Roulette, Baccarat and more.

Dominican Republic

The Dominican Republic has quickly become a favorite among meeting planners looking for a memorable Caribbean locale to host financial and insurance meetings, conventions, leadership summits and events. From the large convention centers in Punta Cana to historical sites in Santo Domingo, the Dominican Republic offers an array of unique cultural and adventure-filled activities for team-building. The island also offers world-class resorts, pristine beaches, off-the-beaten-path ecotourism opportunities and fantastic golfing for groups of all sizes.

Casa de Campo Resort & Villas in the Dominican Republic boasts over 18,000 sf of flexible indoor and outdoor meeting space. From three distinctive conference centers to multiple unique onsite venues, Casa de Campo is designed for business gatherings of all sizes in an extraordinary Caribbean setting. The resort’s all-inclusive amenities means that attendees can explore the multitude of activities, excursions and dining options – streamlining the overall planning experience for meeting planners.

Virgin Islands

With nonstop air service from many major U.S. cities, the U.S. Virgin Islands (USVI) offers a relaxing, creative atmosphere for a distraction-free environment for insurance and financial meetings. Attendees can get out of the corporate environment and enjoy resorts that offer beachfront terraces, oceanfront event lawns and expansive indoor spaces that are ideal for brainstorming sessions, leadership meetings, annual conferences and large-scale conventions.

The Westin St. Thomas Beach Resort & Spa features over 25,000 sf of indoor space and 60,000 sf of outdoor gathering spaces. On St. Croix, the Carambola Beach Resort & Spa is a favorite thanks in part to the resort’s five meeting rooms and nearly 4,000 sf of event space. The Westin St. John Resort Villas provides 3,500 sf of space in a stunning tropical setting.

The main islands of St. Thomas, St. John and St. Croix offer varied attractions, dining and shopping excursions for attendees. Team-building activities, such as corporate day charters, sailing, horseback riding and other local experiences, are available for attendees to enjoy.

Aruba

Aruba is a warm, hospitable destination for financial and insurance meetings. From seaside pavilions to beach clubs to historic landmarks, Aruba boasts a variety of settings where gatherings of all sizes can be held. Meeting planners can also incorporate cultural elements and local traditions to create immersive and memorable experiences for attendees.

Many of the island’s top-tier resorts offer extensive conference facilities, ballrooms and breakout rooms. For example, Hyatt Regency Aruba Resort, Spa & Casino, recently Aruba’s Best MICE hotel, features over 23,000 sf, including boardrooms and ballrooms for large events. The resort’s Events Lawn is a favorite among groups as it offers an ideal space for elegant dining and networking events. The hotel’s beachfront setting also offers a stunning, versatile venue for groups of up to 700 attendees. Multiple pools, cabanas and activities like cooking classes, water volleyball, as well as an expansive spa, provide great relaxation and revitalizing activities for attendees to enjoy.

Like Puerto Rico, U.S. citizens don’t need a passport to travel to the U.S. Virgin Islands. Pictured: Frenchman’s Reef in St. Thomas.

Like Puerto Rico, U.S. citizens don’t need a passport to travel to the U.S. Virgin Islands. Pictured: Frenchman’s Reef in St. Thomas.

Puerto Rico

Puerto Rico is home to a wealth of luxury resorts with extensive event space, as well as a large convention center and two smaller ones that offer plenty of professional meeting amenities for groups of all sizes. As a U.S. territory, Puerto Rico offers the ease of domestic travel with the feel of an exotic getaway, making it a convenient destination for U.S.-based companies.

Old San Juan, an eight square block area that dates back to the early 1500s, is teeming with narrow cobblestone streets studded with cobalt blue stones and pastel-colored buildings with filigreed wrought iron adornments, statue-filled plazas, mosaic-tiled churches and chapels, and red cupolas framing Spanish colonial-style buildings.

Known for its large-scale event capabilities, luxury amenities, private island access and unique activities, El Conquistador Resort offers extensive meeting spaces and a compelling mix of business and pleasure.

Recently, El Conquistador underwent a $250 million transformation, resulting in over 100,000 sf of flexible indoor and outdoor event space, including a modern Grand Ballroom, ocean-view terraces and breakout rooms infused with natural light. Lush gardens and the resort’s private island (accessible by a 15-minute ferry ride) provide a memorable backdrop for meetings. In addition to its white-sandy beach, the resort’s private 100-acre Palomino Island boasts the perfect setting for a once-in-a-lifetime private evening business event.

Located on a 300-foot cliff overlooking the ocean, El Conquistador also offers something very unique – an all-in-one retreat experience that enhances attendee engagement. It also offers easy access to Puerto Rico’s natural attractions, such as the El Yunque National Forest and the bioluminescent bay in Farjardo. The resort provides opportunities for groups of meeting attendees to experience an array of cultural experiences, such as local mixology classes, historical tours and salsa lessons.

The oceanfront El Conquistador Resort in Puerto Rico recently underwent a $250 million renovation.

The oceanfront El Conquistador Resort in Puerto Rico recently underwent a $250 million renovation.

Jamaica

Jamaica offers a unique beauty all its own. All-inclusive resort amenities abound throughout this iconic Caribbean destination. A meeting mecca that celebrates the country’s spirited culture, Montego Bay is an ideal location for event attendees looking to work some and play some.

In addition, the Montego Bay Convention Centre is ideal for large-scale meetings, and the Jamaica Conference Centre, situated on the waterfront in downtown Kingston, offers an array of space, for conventions and small-scale meetings.

The natural beauty of Jamaica is perfect for those seeking offsite adventures such as cliff diving, ziplining, river tubing and more.

The natural beauty of Jamaica is perfect for those seeking offsite adventures such as cliff diving, ziplining, river tubing and more.

The natural beauty of Jamaica is the ideal backdrop for meetings and events. With more than 3,000 species of flowering plants, Jamaica is a wonderland of “all things tropical” and truly is an idyllic paradise for respite seekers and adventure lovers alike. And the region offers unique team-building options for groups including drumming challenges, ATV buggy races, ziplining and river tubing experiences. I&FMM

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