The Jamaica Pegasus has just been named the Caribbean’s Leading Business Hotel 2026 at the World Travel Awards. Before it, only one other hotel had received this title: the Hilton Barbados, in 2007. Between a hotel founded in 1968, a U.S. president, and students seeking shelter from a hurricane, here’s what this award reveals about Kingston.
On October 11, 2026, in Green Island, Hanover Parish, the World Travel Awards presented their trophies for the Caribbean and the Americas. One of them made its way to Kingston. The Jamaica Pegasus was named Caribbean’s Leading Business Hotel, in other words the best business hotel in the Caribbean. As head of the Courtleigh Group, which owns the property, Kevin Hendrickson can savor a moment that has taken nineteen years to come around again.
Competing with it are hotels in Cuba, Trinidad and Tobago, the Dominican Republic, and Jamaica. The Gran Hotel Manzana Kempinski in Havana, the Hyatt Regency Trinidad, the InterContinental Real, and the Sheraton in Santo Domingo are all part of international hotel chains. S Hotel Kingston, which opened in 2009, is even located in the same city as the winner.
Jamaica Pegasus, a title that made a comeback after 2007
This category hasn’t always been known for its consistency. Prior to this year’s competition, only one hotel had ever won it: the Hilton Barbados, in 2007. The Jamaica Pegasus is thus the first winner in nineteen years.
Across the island, the competition remains tight. S Hotel Kingston claimed the Jamaican title for best business hotel. Two hotels in the capital are thus sharing the spotlight, which is a good sign for Kingston. The Jamaica Pegasus also receives this award nearly a year after Hurricane Melissa, a season the island won’t soon forget.
A hotel founded in 1968 that has become Jamaican
The story begins in 1968. A company was formed as a joint venture between the airline BOAC, now British Airways, the Trusthouse Forte Group, and the Jamaican people. The hotel opened partially in 1973 to host a major convention, and then officially in September of that same year.
In 1976, the Jamaican government acquired a stake in the company. In 2002, management returned to local hands. Around 2010 and 2011, Kevin Hendrickson’s group acquired full ownership. Hendrickson was named Caribbean Hotelier of the Year in 2022 by the Caribbean Hotel and Tourism Association. Today, the Jamaica Pegasus boasts an all-Jamaican staff. The story of a hotel built with foreign capital and later taken over by local ownership is no mere detail. It explains why this victory is celebrated in Kingston as a matter for the extended family, well beyond the board of directors alone.
Jamaica Pegasus: The Business Side and Behind the Scenes
Heads of state are familiar with the hotel. On April 8, 2015, Barack Obama arrived in Kingston and checked into the hotel. There, he met with staff from the U.S. Embassy, went to visit the Bob Marley Museum, and then returned to spend the night. Three weeks before his arrival, the hotel had stopped taking reservations. That is sometimes the price of having the honor of hosting a president. For a business hotel, closing its doors to regular guests for three weeks is a gamble, and the Jamaica Pegasus took it.
Day-to-day operations revolve more around meetings, conferences, and trade shows, what the industry calls the MICE sector, short for meetings, incentives, conferences, and exhibitions. Here, too, the hotel was named the best in Jamaica in 2021 and again in 2024. It has proven its ability to accommodate guests on short notice. In late October 2025, as Hurricane Melissa approached the island, the government of Antigua and Barbuda secured two nights of accommodations, including meals, for its students who were in Jamaica. The hotel served as a shelter before it served as a conference venue.
What This Award Says, and What It Doesn't Say
A quick word of honesty. The World Travel Awards are determined by online voting. Travel industry executives and travelers choose their favorites, and the vote of a verified professional counts double. There is no jury to decide the outcome, and the Jamaica Pegasus plays by these rules. This award, therefore, measures popularity, not the results of an inspection.
Yet this reputation matters, because business travelers often choose a hotel they’ve heard of before. The votes measure this reputation. Nassau, in the Bahamas, was voted the best Caribbean business destination, while Kingston ranks first in terms of hotels. The two rankings complement each other and paint a picture of the Caribbean that goes beyond its beaches.
There’s just one more step to go. The Jamaica Pegasus is also nominated for the title of World’s Leading Business Hotel 2026. Will business travelers choose the Kingston tower this time over the big international names? The answer will reveal whether the Jamaica Pegasus, born out of a convention in 1973, can speak to the whole world from Jamaica. The outcome will now be decided by the digital vote.
Frequently Asked Questions
The Jamaica Pegasus in Kingston, Jamaica, won this World Travel Awards prize. The Caribbean & The Americas gala was held on October 11, 2026, at the Princess Grand Jamaica in Hanover.
No. The award had already been presented in 2007 at the Hilton Barbados. The Jamaica Pegasus is the first recipient since then.
Through an online vote by travel industry executives and consumers. Each verified professional’s vote counts double, and the votes are audited.
