The Best (and Last) Regatta on Earth

Published on May 20th, 2020

Meg Reilly is a circumnavigator who runs an international sailing team, Ocean Racers, with her partner Morgen Watson on their Pogo 12.50 Hermes. The duo has been quarantined on anchor in St Maarten, where the last race of their season left them.

As we prepare to finally depart from St Maarten, after over two months ‘stuck’ in paradise, I can’t help but reminisce about the Caribbean racing season that came and went too soon.

For us, the Caribbean 600 is a roaring start, immediately followed by the St Maarten Heineken Regatta in which we get into the rhythm for the marathon of regattas. And if your first lap is any indication of your overall performance, this was setting up to be a PB (personal best) of a season for us.

But we weren’t given the chance. Just a week after the St Maarten Heineken Regatta came to a close, COVID-19 began closing borders (and regattas) across the Caribbean, the US, and the rest of the world. It’s not like we were completely ignorant to the virus on the island; there were CDC warnings flashing on billboards, we had personalized no-share water bottles on our boat, and a hand sanitizer station greeted you on entrance to the regatta village with advice to party with caution.

Later we’d learn, we were amidst a global pandemic, and here we were in close contact with thousands of sailors from around the world. But we were fine, our NY-based crew was fine, and I wonder what percentage of sailors actually returned home healthy and well despite the supposed heighten risk scenario we were exposed to. Were our simple health and sanitation precautions enough to have kept us safe? Knowing what we know now, what will the regattas of the future look like?

Although we wish we could, we cannot predict the future. But the gleeful pre-COVID-crisis days deserve reflection, and a self determination as to what level of ignorance is truly bliss. Whatever your personal opinion or experience with the virus, we can all agree: carpe diem and party like it’s your last regatta. Without even knowing the stark reality, that is exactly what we did.

The St Maarten Heineken Regatta always had a special place in our hearts, as it is hosted in the port that we call home each winter. But aside from our bias, it actually is one of the best, if not the best, regattas for a variety of reasons.

All regattas strive to find the perfect mix of work hard – play hard, between the hot racing series on the water and a plethora of fun once you get ashore. But sometimes too much of a good thing can be… too much. Yet Heineken Regatta has figured out the perfect formula. Instead of pushing the limit of sailing and drinking over a full week as a combined sport, they lay it out in 4 days of non-stop fun.

Regatta aficionados know that the beloved “lay day” is a blessing and a curse as you break the sailing stride — but not the partying — and the recovery is slow going. St Maarten Heineken Regatta instead skips lay day, leaving the big blowout day for partying to be Sunday, keeping racers focused through the long weekend of racing.

It’s something to keep working towards, leaving the climax for the very end. Or at least that’s what we try to tell our inbound crew, who preferred to learn the hard way, arriving with a banger (and similar head ache the next day) instead of the slow rolling start us regatta veterans strongly advised.

Regardless, this year’s climax was headliner Flo Rida, who brought down the house in true music-festival style. The Heineken girls handed out green glow bracelets to the crowds, their dancing counterparts graced the stage in flashy Carnival costumes, while your choice of drinks were bountiful to take you through the night and into the early AM. I’m not a beer drinker myself, but sponsorship from Veuve Clicquot and the legendary jumbo mojitos kept me more than happy.

The “something for everyone” theme continued on the race course. Finally, we were matched in OUR class. Ocean Racing 2, with our Pogo 12.50 and Class 40s only, for the first time racing inshore against the right boats on courses made just for us. New Race Director Marc van Dongen drew a firm line in who was allowed to be in the Ocean Racing classes, and the offshore pedigree requirement preserved the closest inshore racing us ocean racers have ever had!

Just because you were a big boat or blue-water cruiser did not mean you earned a spot in the Ocean Racing classes. Instead, the CSA classes were better allocated between size and might, leaving the Ocean Racing classes for Volvo Ocean Race veterans and our Class40 comrades who rightfully earned the classification. Nothing beats the feeling when offshore boats who desperately try to fit in at inshore regattas are finally recognized in a league of their own.

You know the classes and courses are expertly formed when the racing is so close. Our first day we got two bullets, then spent the rest of the weekend vying for the top podium position. It was match racing at its finest! While our ratings were still handicapped, the first upwind legs were spent trading positions with pucker ducks and close-call battles to the marks.

“Serious Fun” is a well-earned tagline for the St Maarten Heineken Regatta. This year you could tell that the RC took their jobs very seriously, designing on-point courses for all classes, always starting on time and keeping communications clear and concise. Previous years it seemed that the party had taken precedence over racing, but this year we were racing long courses to the last possible moment that allowed you to catch the 3 PM or even 5 PM bridge back into Simpson Bay Lagoon.

Now it all seems like a lifetime ago, but it makes it easier to leave and return with such a good taste left in your mouth. While Simpson Bay is now empty, we can still look out on the water and remember when it was once packed with yachts from around the world. For many, it was the last regatta for a while, but one that we all look back on fondly. And we can only hope that the Regatta will return next year to not only be as good, but better than the last.

We welcome you to join us for a 2021 Regatta season, which will hopefully host a big comeback as the Caribbean always has through tough times in the past. Visit to book 2021 regattas at 2020 rates, and follow the team on @oceanracers Facebook and Instagram for your sailing fix as we make our journey up to the US for hurricane season.

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