AI Agents Are Starting to Choose Jamaica's Next Tourists. The Island's Tourism Board Is Racing to Be Understood by Them.

On 23 September 2026, the Jamaica Gleaner reported that the Jamaica Tourist Board is trying to solve a problem no tourism board has faced before: how a chatbot decides which Jamaican hotel to recommend. Four days later, that same problem became the theme of a national campaign. Jamaica's Tourism Awareness Week 2026, running 27 September to 3 October under the banner "Digital Agenda and Artificial Intelligence to Redesign Tourism," is the government's public answer to a shift the industry can already measure in traveller behaviour, even if it cannot yet measure what that shift is worth in bookings.

Jamaican tourism officials are preparing for a period in which travellers increasingly ask an AI assistant, rather than a search engine, where to stay and what to book, and the Jamaica Tourist Board (JTB) is restructuring how the island's businesses present themselves online so those systems can find and recommend them. The clearest sign of how seriously government is treating this: an entire national tourism week now carries an AI theme, with a youth forum, an industry workshop, and messaging built around one idea, that Jamaica's next visitor might be chosen by a machine before a human ever opens a browser.

Jamaica's north coast, the stretch of coastline the Jamaica Tourist Board's AI-readiness push is meant to protect. Photo: Unsplash

A Trade Show Warning, Then a National Theme

The shift did not start with a government press release. It started at a hotel trade show. At the Jamaica Hotel and Tourist Association's Jamaica Product Exchange (JAPEX), held 14 to 17 September 2026 at Moon Palace Jamaica in Ocho Rios, Accenture Song's Dean Challis, an AI strategist who serves as managing director and head of media and innovation for EMEA, told a room of hoteliers and tour operators about what he called agentic commerce: AI systems that plan, book and pay on a traveller's behalf instead of just answering questions. Citing Booking.com's 2025 Global Sentiment Report, Challis said 60 percent of consumers have already used AI to plan a trip, 91 percent are excited about the technology, and 89 percent want to use it again on their next one.

Challis made the risk concrete with a case study. Radisson Hotel Group, working with Accenture, has already launched an AI-powered hotel discovery tool inside ChatGPT, letting travellers search more than 1,000 Radisson properties across over 100 countries through ordinary conversation instead of a booking site's search filters. For a traveller, that is convenience. For a destination competing for the same attention, it is a preview of who gets found and who does not.

What the Tourism Board Is Actually Worried About

Nine days after JAPEX closed, Kristopher DaCosta, the JTB's global travel marketing leader, told the Gleaner that the shift is already underway. Travellers, he said, are asking AI assistants questions like "Where should I go? What's a good Caribbean destination? Build me an itinerary," and getting answers built from whatever data the assistant can parse. His warning was specific: "If we do nothing, there is a real possibility that AI disproportionately recommends the businesses that are easiest for machines to understand."

DaCosta framed the task as a matter of legibility rather than marketing. "Can a machine determine who you are, where you're located, what you offer, whether the information is current, and how someone books with you?" he asked. He placed the shift in the same lineage as two earlier ones the JTB has had to manage: "Twenty years ago, we had to make Jamaica searchable. Then we had to make Jamaica social and mobile. Now we have to make Jamaica understandable and actionable by intelligent systems." He was candid about the limits of what the board actually knows here: the JTB cannot yet quantify how much business AI-driven recommendations are sending to the island, which makes the current push as much a bet as a strategy.

The Size Mismatch Behind the Warning

The businesses DaCosta is describing are not abstract. Paul Salmon, owner of the Rockhouse Hotel in Negril, a boutique cliffside property built on three decades of repeat guests and word of mouth, is the kind of operator that could disappear into an AI system's blind spot: a small, independently run hotel whose room policies, menus and booking terms live on a website built for a human reader, not for a language model parsing structured data. Set that against Radisson's 1,000-property ChatGPT integration and the mismatch DaCosta is naming becomes obvious. A traveller who asks an AI assistant to find a boutique hotel in Negril gets an answer only as good as whatever structured information exists for that hotel to be found by.

The view a boutique Jamaican property sells to a guest. The question DaCosta is raising is whether an AI system can find that property at all. Photo: Unsplash

The Money Already on the Table

The stakes are not abstract either. Jamaica welcomed 2.34 million visitors and earned US$2.5 billion in the first eight months of 2026, according to Jamaica Tourist Board figures, on a trajectory the Ministry of Tourism has framed as a "5x5x5" target: five million visitors and US$5 billion in annual earnings within five years, en route to eight million visitors and US$10 billion by 2030. Tourism accounts for a large share of the island's foreign exchange earnings, and a shift in how AI systems recommend destinations, hotels and experiences touches nearly every part of that number, from resort bookings down to the tour operator who takes visitors up into the Blue Mountains.

A Sector That Already Learned This Lesson Once

Jamaica has recent, painful experience with what happens when a digital shift outruns institutional readiness. Jamaica's National Security Council, chaired by Prime Minister Andrew Holness, declared lottery scamming a national security threat on 23 July 2026, after the island's Business Process Outsourcing sector, the call centre and back-office industry that once employed roughly 60,000 people, saw that number fall to about 40,000, according to Jamaica Observer and Gleaner reporting on the council's decision. The scam economy that grew inside legitimate call centre infrastructure cost the sector billions of dollars in reputational and direct damage before government treated it as core to the industry's survival rather than background noise. Nobody is suggesting AI travel recommendations carry the same kind of risk. The parallel that matters is procedural: a technology shift moved faster than the institutions meant to manage it, and Jamaica paid for the gap in lost jobs. Tourism officials appear to be trying not to repeat that sequence.

What Tourism Awareness Week 2026 Actually Does

The government's response opens Sunday 27 September with a Thanksgiving church service in Montego Bay at Faith Temple Assemblies of God, and runs a Speaker Series at Tourism Action Club schools on 28 and 29 September and again on 1 and 2 October. The programme's two substantive events land midweek: the Tourism AI Youth Forum on Wednesday 30 September, where students take part in an AI challenge and hear from tourism and technology professionals about careers the sector is creating, and a "Hospitality & Tourism: AI in Tourism" workshop on Thursday 1 October at the Jamaica Centre for Tourism Innovation, aimed at operators rather than students.

Minister of Tourism Edmund Bartlett framed the week's intent plainly. "Tourism is being transformed and the pace of technological change means that Jamaica must not simply respond to the future, we must help to shape it," he said. Director of Tourism Donovan White added the caveat that matters most for an island whose brand depends on more than efficiency: "Technology must enhance, not replace, the Jamaica experience. Our hospitality, authenticity, creativity and human connection remain central to what visitors come here to experience."

What a Jamaican Tourism Business Can Actually Do This Week

The practical advice from JAPEX and from the JTB itself is not complicated, even if it requires work most small operators have never had reason to do. Claim and fully complete a Google Business Profile with accurate hours, pricing and amenities, since that structured listing is one of the clearest sources an AI assistant can parse. Keep website information current rather than seasonal, because a model recommending a restaurant or tour operator has no way to know a menu changed six months ago unless the page says so. Add basic schema markup, the structured data tags search engines and AI systems both read, to hotel, restaurant and attraction pages, a step most Jamaican small business websites have never been built to include. None of it replaces the service a guest actually receives on arrival. All of it decides whether that guest finds the business in the first place.

Adrian Dunkley, president of the Caribbean AI Association and founder of StarApple AI, the Caribbean's first AI company, built in Kingston in 2016, has made a version of this argument for years about industries well beyond tourism: that Caribbean businesses need to treat their own data with the same discipline banks apply to compliance data, structured, verifiable, and built to be read by a machine, not just by a guest.

"If di system cyaan find yuh, it cyaan sell yuh," Dunkley said of the shift DaCosta is describing, "and no amount of good service inna di lobby is gwine fix that."

The Caribbean AI Association, which he leads, has flagged exactly the readiness gap Tourism Awareness Week is trying to close: most small and mid-sized Caribbean tourism operators have no one on staff responsible for how their business appears to an AI system, largely because until this year, almost nobody needed one.

Whether Tourism Awareness Week changes actual booking numbers is not something the JTB can measure yet, by DaCosta's own admission. What it does measure is intent: a government putting a national week's worth of programming behind the idea that the next tourist to discover Jamaica might never type the word "Jamaica" into a search bar at all.

Dunkley's writing on AI readiness across Caribbean industries is collected at adriandunkley.net. The Caribbean AI Association, which he leads as President, and StarApple AI, the company he founded, both publish material on the data and governance questions this week's programming is trying to answer for tourism specifically.

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