Anguilla’s Tourism Chief Pushes Regional Unity

The Caribbean has a marketing problem, and it isn’t the islands competing with each other for the same American beachgoer. According to Anguilla’s tourism chief, the real rivals are half a world away — and it’s time the region stopped fighting itself long enough to notice.

Jameel Rochester, at 33 the youngest person and first man ever to serve as Director of Tourism for the Anguilla Tourist Board, laid out that argument in a recent interview with Lawrence Boschulte on 90.9 FM, run by the Caribbean Broadcast Network in the British Virgin Islands. His message: Anguilla isn’t really competing against St. Barths or the BVI for the discerning traveler’s attention. It’s competing against Seychelles, Dubai, Fiji and Bora Bora — and no single 35-square-mile island can win that fight alone.

A Different Kind of Rivalry

It’s a subtle but important reframing for an industry that has, for decades, treated its neighboring islands as the primary threat. Rochester’s pitch is that Caribbean destinations pooling their strengths — rather than undercutting each other on price or poaching each other’s marketing dollars — is the only realistic way to hold ground against the far-flung luxury destinations increasingly courting the same high-spending traveler.

Practically, that means encouraging multi-island itineraries that link Anguilla with the U.S. Virgin Islands, the British Virgin Islands, St. Maarten-Saint-Martin, St. Barthélemy and other nearby destinations, turning a single-island vacation into a longer, richer regional trip. For travelers, that’s a genuinely useful idea: hop from Anguilla’s quiet, undeveloped beaches to St. Barth’s for a night out, or pair a stay in the BVI with Anguilla’s slower pace, all without the 20-hour flights required to reach Fiji or the Seychelles.

The timing is notable. The Caribbean just closed out a record year — roughly 35 million stayover arrivals in 2025, a 2.5% increase over 2024, according to the Caribbean Tourism Organization, marking the third consecutive year the region has outpaced its pre-pandemic 2019 benchmark. Early 2026 has kept that momentum largely intact, though performance has varied sharply by destination: Jamaica saw stayover arrivals drop 27.5% in the first quarter due to the lingering effects of Hurricane Melissa, even as it later crossed the 1-million-visitor mark for the quarter, while Bermuda and Antigua and Barbuda both posted solid single-digit gains. Against that uneven backdrop, Rochester’s call for islands to cooperate rather than compete carries extra weight — a rising tide doesn’t lift every island equally, but a coordinated one might come closer.

Anguilla’s Own Numbers Tell the Story

Rochester has plenty of momentum behind him at home. Anguilla posted the highest stayover visitor growth of any reporting Caribbean destination in the first quarter of 2026, according to CTO figures: 46,691 stayover visitors between January and March, a 24.6% jump over the same period last year. For an island with a resident population under 20,000, that’s a significant surge, and it puts Anguilla well ahead of the region’s broader growth trend.

Part of that growth traces back to improved air access — a second pillar of Rochester’s strategy alongside workforce development and regional cooperation. He pointed to nonstop American Airlines service from Miami, BermudAir/AnguillAir flights connecting the island to the U.S. and Canada, and expanded routing options through Turks and Caicos as key drivers. Those connections matter beyond convenience: they’re also strengthening links between Anguilla and other British Overseas Territories in the region, giving international travelers more flexible ways to reach the island without funneling everyone through the same one or two gateway airports.

That kind of connectivity investment mirrors a broader shift happening across the region. Intra-regional carriers like Caribbean Airlines and interCaribbean Airways have been expanding seat capacity, making island-hopping easier without the traditional backtrack through Miami or San Juan — exactly the kind of infrastructure Rochester’s multi-island vision depends on.

Redefining Luxury — and Who Gets to Benefit From It

Rochester describes Anguilla’s positioning as “luxury inclusive,” a phrase meant to convey that the island’s beaches, restaurants and experiences are accessible across a range of spending levels, not reserved exclusively for five-star resort guests. It’s a deliberate contrast to the ultra-exclusive image Anguilla has carried for years, and it fits the island’s “Lose the Crowd. Find Yourself.” campaign, which leans into simplicity and quiet rather than spectacle. As Rochester put it, Anguilla is “something to somebody, but not everything to everybody” — a candid acknowledgment that the island isn’t chasing every traveler segment, just the ones who want what it actually offers.

But the more striking part of Rochester’s platform is who he wants running that experience. His central argument is that tourism revenue needs to visibly benefit the people of the destinations generating it — and that means moving young Anguillians beyond entry-level hospitality roles and into management and ownership positions. He’s pushed back specifically on the idea that tourism careers top out at “dishwasher and server and clerk,” arguing that leadership pathways need to be made visible and attainable much earlier.

Rochester’s own résumé makes the case: stints in banking and at properties including Malliouhana, Zemi Beach House, Cap Juluca and Four Seasons Anguilla, followed by a role at Wymara Resort + Villas in Turks and Caicos, a Caribbean Hotel and Tourism Association scholarship, an MBA from Les Roches in Spain, and undergraduate study at the University of the West Indies, Mona. He’s also served as General Secretary of the Anguilla Football Association, expanding youth sports programming — a background that suggests his interest in workforce pipelines extends well beyond the resort industry.

This isn’t a niche concern. Across the wider Caribbean, tourism accounts for a huge share of GDP and employment in small island economies, yet local ownership of hotels, tour operations and other tourism assets often lags behind foreign investment. A workforce strategy that pushes locals toward senior roles — not just service jobs — addresses a structural gap the industry has wrestled with for years, and it’s one other destinations are likely watching closely.

For travelers weighing Caribbean options this year, Rochester’s comments offer a useful signal: Anguilla is investing in growth without losing its identity, and it’s angling to be part of a more connected, cooperative regional network rather than a standalone stop. If that regional pitch gains traction, it could mean smoother, more affordable ways to combine an Anguilla stay with a hop to St. Barths, the BVI or St. Maarten — itineraries that are currently more the province of yacht charters and private jets than mainstream travel planning.

It’s also a reminder that “luxury” in the Caribbean doesn’t have to mean exclusivity in the way it once did. Anguilla’s pitch — quiet beaches, high-quality food and service, but access at multiple price points — runs counter to the ultra-velvet-rope positioning some competing luxury destinations lean on.

Whether Caribbean destinations can genuinely coordinate rather than compete remains an open question — tourism boards have talked about regional cooperation for years without always following through, hampered by different currencies, visa regimes, air links and marketing budgets. But Rochester’s framing, that the real competition sits in the Indian Ocean and South Pacific rather than the next island over, is a useful gut check for an industry that sometimes forgets how small its internal rivalries look next to the global luxury travel map. If Anguilla’s early-2026 growth numbers are any indication, that outward-facing approach — paired with better air access and a workforce built to lead, not just serve — may be paying off already.

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