Caribbean Travel, Reimagined: How Casey Davy Is Building A More Connected Caribbean For Travelers And Locals

For generations, the best Caribbean experiences lived off the grid — no websites, no booking apps, just a neighbor who knows a boat captain or a local chef. Montreal-born, island-raised founder Casey Davy saw both the magic and the friction up close — and set out to bring the region into a more connected, digital future.

When you ask Casey Davy what makes the Caribbean special, he doesn’t hesitate. “The people,” he says. “Beaches we can find everywhere, but there’s something unique about the Caribbean. It’s the people and those authentic experiences that make it so special.”

As the founder of Caribbean Travel & Tours (CTT) and its parent company, Breeze Travel Solutions, he’s building a platform designed to make the Caribbean easier to explore and, more importantly, easier for Caribbean people to benefit from.

Building A Bridge Between Islands And Innovation

Caribbean Travel & Tours is designed to address the region’s realities: fragmented suppliers, limited online presence, and travelers hungry for real local culture. Backed by years in travel tech and destination partnerships, CTT bundles flights, accommodations, transfers, tours, and community-led experiences — then layers on AI, multi-island itineraries, and an in-destination app to guide travelers on the ground.

Before Caribbean Travel & Tours, Davy was already deep in the travel-tech game. His background in media and marketing led him into hospitality systems long before most of us were booking vacations online. In the late 2000s, as sites like Expedia and Booking.com reshaped the industry, he co-founded Busy Rooms, a hotel management and distribution platform that grew from 80 clients to over 2,500 worldwide.

It was during that rise that Davy began to see the Caribbean’s potential in a new light. While Europe and North America were leaning into digital transformation, the Caribbean still relied on personal connections and word of mouth.

“You often have to know somebody,” he says. “Because this vendor doesn’t have a website, or that one isn’t on Instagram.”

For a long time, Davy resisted turning his professional eye toward home. “The Caribbean was my place of refuge,” he admits. “It was where I went to relax. The idea of doing business there was daunting.”

But the pandemic changed everything. When travel paused, Davy took it as a chance to reset. He launched Breeze Travel Solutions to help Caribbean hotels and tourism boards digitize, and the work quickly revealed a bigger opportunity.

By 2023, that early effort evolved into Caribbean Travel & Tours, a full-scale marketplace connecting travelers with the people and places that make the Caribbean magical. The goal wasn’t to turn the islands into something new — it was to make what already exists easier to find.

Turning Word-of-Mouth Into A Marketplace

If you’ve ever planned a Caribbean trip, you know it can take a village — and a cousin’s friend’s WhatsApp contact — to pull it all together. CTT was built to change that.

The platform functions as a hub for flights, hotels, tours, and transportation, but it’s far from a cookie-cutter booking site. Davy calls it a marketplace, not an online travel agency (OTA), built to serve everyone from global travelers to boutique tour guides.

“We’re not an online travel agent,” he explains. “We’re a marketplace that connects everyone — from the five-star resort to the guy giving kayak tours on the Rio Grande.”

Users can choose from three main experiences:

1. Pre-curated itineraries, designed with destinations and local curators, from wellness escapes to cultural deep-dives.
2. Build-your-own trips, for travelers who want flexibility and control.
3. AI-assisted planning, which helps match you with places and experiences you might not discover otherwise.

CTT also unlocks multi-island travel, something most platforms can’t handle due to the region’s fragmented transport systems. “We wanted people to experience the region seamlessly,” Davy says. “In 2026, we’ll even have multi-island Carnival itineraries — St. Vincent and St. Lucia, Barbados and Grenada, or all four for the true Carnival warriors.”

For those already on the ground, the company’s in-destination app acts as a pocket-sized guide. Using location data, the app highlights nearby spots and hidden gems.

“If you’re in Jamaica’s Blue Mountains,” he says, “the app might tell you to stop for lunch at Strawberry Hill. Or in Barbados, it might point you to the best bread pudding on the island.”

What makes this approach especially powerful is its impact on smaller, community-based operators who’ve never had the tools or budget to market themselves globally. Through the app, they’re visible — not buried beneath the algorithms of big travel brands.

“Caribbean Travel & Tours is a one-stop shop for booking everything you need in the Caribbean,” Davy says. “And it gives local people a platform to be seen.”

Powering The Future Of Caribbean Tourism

Behind the glossy design and tech integrations, CTT’s deeper purpose is clear: keep more Caribbean wealth in the Caribbean.

“We’re always trying to make sure that some of the revenue being generated in the Caribbean actually stays in the Caribbean,” Davy says.

Through Breeze Travel Solutions, his team partners directly with governments, tourism boards, and community organizations to help local businesses get online. That might mean setting up a digital reservation system for a seven-room boutique hotel, or building a simple website for a tour guide who’s been running the same beloved boat trip for 20 years.

“Sometimes it’s as simple as building a small website for a boutique hotel that had none,” Davy says. “We’re really trying to help them help themselves.”

Then there’s the Influencer Program, which flips the traditional pay-per-post model into something more sustainable. Creators who visit a destination can now curate their own itineraries and earn commissions on every booking that comes through their link.

“They do earn, and that commission ranges from 5% up to 10%,” he explains. “We handle the licensing and logistics; they just need to focus on the creative.”

This fall, the company is also introducing the first of its Culinary Ambassador series, featuring Barbados-born, Miami-based Chef Paul Griffith. Guests will learn to cook Caribbean dishes from scratch while hearing the origin stories behind each meal.

Food, Davy says, is one of the purest ways to understand a culture — and one of the best ways to export it.

A Future Built By The Region, For The Region

Beyond the plate, CTT is already looking toward the future. The team is investing heavily in AI and voice technology to make sure Caribbean operators remain discoverable as search evolves.

“We’re trying to future-proof Caribbean destinations for what’s to come,” he says. “If these operators aren’t digitized, they won’t be found — unless you happen to have a friend on the ground.”

For Davy, though, the work is about more than code, commission structures, or bookings. It’s about changing what’s possible for Caribbean people in an industry that defines their region.

“Tourism isn’t just being a concierge or a driver,” he says. “There’s technology, there’s asset management, there’s marketing. There’s an opportunity for people to build generational wealth.”

Caribbean Travel & Tours serves as a bridge between travelers seeking connection and the local communities ready to share it. Each partnership and curated experience builds toward a shared vision: keeping the region’s stories, creativity, and opportunities in the hands of the people who call it home. In Davy’s eyes, that’s what progress in the Caribbean should look like — modern, collaborative, and rooted in culture.

This article has been edited and condensed for length and clarity.

The post Caribbean Travel, Reimagined: How Casey Davy Is Building A More Connected Caribbean For Travelers And Locals appeared first on Travel Noire.