The 2026 Caribbean Sports Calendar

Whatsup Squad,

Caribbean sports coverage just got a major upgrade.

Allow me to reintroduce the Caribbean Sports Calendar, currently featuring 80 events across 11 sports and 21 countries.

You can check it out here.

Why This Matters: Calendars and Sports Tripping

Global sports tourism is projected to be a $2 TRILLION industry by 2032, a massive surge from the $707 billion it was worth last year.

The concept of people traveling to participate in or spectate sporting events is often referred to as “sports tourism”, but I prefer to call it sports-tripping.

Regardless of what you call it, this phenomenon has exploded over the last few years.

In the United States, companies like OnLocation provide a full calendar of events that let sports fans book travel packages directly.

In mature markets, this behavior is clearly here to stay. But in emerging markets, it’s just getting started.

The Caribbean is perfectly positioned to capitalize on sports-tripping because the region is disproportionately reliant on tourism for employment and economic growth.

Don’t believe me? Believe Carole Beckford.

Her career spans three decades of work in media, marketing, communications and PR, highlighted by her role as a Publicist for Usain Bolt during his rise to global stardom.

In her latest article, Carole explained:

“Sports tourism should not be treated as something peripheral, it has to be treated as a formal pillar of regional economic planning.”

But here’s the problem: you can’t plan a trip around these sporting events if you don’t know they exist.

Right now, Caribbean sports events are scattered across federation websites, social media pages, and local news outlets. There’s no single source showing the full picture.

Fans miss opportunities. Media can’t plan coverage. Sponsors overlook activation moments. Local economies lose tourism dollars.

That’s where a comprehensive calendar becomes critical infrastructure.

What I Built

This is not the first Caribbean Sports Calendar I created, but it is a major step up from last year’s version.

Not only does it include almost double the amount of events, but it is searchable, mobile-first, and interactive.

Filter by sport to track basketball across the region, filter by country to plan your Jamaica trip, or view the full calendar to see what’s happening during your travel window.

Once you find an event, you can explore viewing options or add it directly to your personal calendar.

Breaking Down the Highlights

First up in February is The XXV Winter Olympic Games, featuring Caribbean athletes from Jamaica (alpine skiing and bobsled), Haiti (alpine skiing and cross country skiing), and Trinidad and Tobago (alpine skiing).

Then West Indies cricket takes on the world at the ICC T20 World Cup in India and Sri Lanka.

At the end of that month, Jamaica hosts the Bahamas in Kingston for a shot at the FIBA 2027 World Cup.

The biggest year in Caribbean sports continues with the FIFA World Cup in June. Haiti and Curaçao have already qualified, but Jamaica still has a chance.

And in August, the Caribbean Premier League (CPL) gets underway, with Barbados’ Kensington Oval set to host the final for the first time ever.

What’s Next

In the near term, I’m adding a way for users to submit events to keep the calendar comprehensive and up-to-date.

I also plan to integrate this calendar more deeply into BACKCOURT content, featuring upcoming events in the newsletter and highlighting them across social media.

Long-term, I could see this expanding beyond sports to other forms of entertainment like concerts and carnivals.

My goal is simple: make this THE go-to resource for sports-tripping in the Caribbean. But I’ll need your help. What events or features are missing?

Final Thoughts

When Caribbean sports are easier to find, more people show up (physically and digitally).

That’s good for athletes, good for federations, and good for the region’s economy.

So explore the calendar, share it, and use it to plan your trip to the Caribbean.

Until next time ✌🏾

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