The St. Maarten Heineken Regatta runs every year in the first week of March in Simpson Bay, Sint Maarten, and it has been running since 1981. It is the largest regatta in the Caribbean and likely the largest warm water regatta in the world. The motto is Serious Fun, and the motto is accurate in both directions: the racing is serious, with world-class race committees, competitive fleets from more than thirty countries, and the specific quality of Caribbean trade wind sailing that the northeast trades off Sint Maarten produce in March when they are most consistent.
And the fun is serious in the way that only the Caribbean in racing mode can produce it: the days on the water followed by the nights in the Regatta Village, the music, the Heineken, the specific atmosphere of a thousand sailors who have been racing hard since dawn and who are very pleased to be in Sint Maarten rather than anywhere else.
I have been to the Heineken Regatta before. More than once. The memories it carries are the memories of the specific combination that the event produces and that no other event on the sailing calendar replicates in quite the same form: the competitive racing in the mornings and the afternoons, the specific camaraderie of the fleet at anchor in the evenings, and the particular quality of the Sint Maarten night that the Regatta Village provides for the four days of the event. It is on the list of things I remember about the offshore sailing life with the specific warmth that the things worth remembering carry.
Where the Naora Voyage Is in March 2028
In March 2028, the Naora circumnavigation is in the Caribbean. The Eighty2 crosses the Atlantic in November 2027 in the northeast trade winds from the Canaries, arrives in the Eastern Caribbean in December, and spends the Caribbean dry season moving through the island chain westward toward Panama and the Pacific departure in April 2028. March 2028 is the heart of the Caribbean chapter: the best sailing conditions of the Caribbean year, the consistent trade winds, the specific quality of the Caribbean spring that the sailing world has been organising its calendar around since the race circuit established itself in these waters.
Sint Maarten in the first week of March 2028 is therefore not a detour from the Naora route. It is, depending on how the specific legs of the Caribbean chapter are sequenced, a port that the route is passing through or very close to. The Heineken Regatta’s 48th edition will be happening in the first week of March 2028. The Eighty2 will be in the Caribbean. The specific question of whether we enter is a question we have not yet answered, and I want to be honest about that rather than announcing a participation that is not yet confirmed.
Why We Are Considering It
The Heineken Regatta is not a race for the Naora voyage in the competitive sense of the vessel whose campaign is built around the result. The Eighty2 is a 24-metre offshore catamaran configured for a five-year circumnavigation: the dive compressor, the dual watermakers, the lithium battery bank, the systems redundancy that the offshore life requires.
It is not the stripped-out racing machine that the CSA1 fleet front-runners campaign. It is, however, a large and capable offshore catamaran in the specific conditions that the Heineken Regatta produces, and the specific pleasure of the event is not reserved exclusively for the boats at the front of the racing fleet.
The Heineken Regatta is genuinely a regatta for everyone, including professional teams sailing Maxis, Monohulls and Performance Multihulls to holiday-makers on chartered Bareboats to live-aboard families cruising the Caribbean. This is the quality of the event that I remember from the previous editions and that makes the question of participation worth asking rather than dismissing: the Heineken Regatta is the race that contains the competitive fleet and the cruising fleet and the bareboat fleet and the one-design fleet simultaneously, and the racing that the Eighty2 would do in the multihull class is the racing of a boat that is fully present in the race rather than a boat that has strayed into a competition it was not built for.
The other reason we are considering it is the Naora Circle. The members who are aboard the Caribbean legs of the circumnavigation in March 2028 are the members who boarded after the Atlantic crossing and who are in the Caribbean for the specific quality of the Caribbean chapter before the Pacific departure. The Heineken Regatta is the specific quality of the Caribbean chapter in concentrated form: four days of the sailing life at its most festive, in the destination that the Caribbean circuit considers its marquee event, in the conditions that the Caribbean trade wind winter produces at its most consistent.
If the Naora is in the Caribbean in March 2028 and the Heineken Regatta is happening, the question of whether to be part of it is the question of whether the members aboard would want the Heineken Regatta to be part of their Caribbean chapter. Based on the memories the event carries, the answer is probably yes.
What the Heineken Regatta Is
For the Naora member who has not been to Sint Maarten and who is considering the Caribbean leg in early 2028, the Heineken Regatta deserves a proper description rather than the assumption that the name explains itself.
The event attracts well over 20,000 visitors annually, from young professionals to businesspersons, from party-goers to international sailors, aging from 18 to 55+ coming from over 37 different countries. With over 1,000 sailors plus thousands more who come to the nightly parties, the St. Maarten Heineken Regatta is one of the biggest cultural events in the Caribbean, running for over four decades the first week of March.
The racing happens during the day in the consistent northeast trade winds off the coast of Sint Maarten, with boats ranging across multiple divisions for CSA monohull and multihull boats along with racing in one design and bareboat fleets.
The evenings are the Regatta Village: the specific atmosphere of the Sint Maarten waterfront when the racing fleet is in and the Caribbean night has begun and the music and the Heineken and the gathering of the crews from thirty-seven countries in the specific shared space of the event that knows how to hold both the serious racing people and the serious fun people in the same location without either group feeling that the other has colonised the event. This is rarer than it sounds. Most sailing events are either fully competitive or fully social. The Heineken Regatta is genuinely both.
Sint Maarten Itself
Sint Maarten is one of the more specific islands in the Caribbean in the sense that it is the same island as Saint Martin: the Dutch half and the French half of a 37-square-kilometre island that has been shared between two countries since 1648 without a fence or a border crossing and with the specific quality of a place that has been international for so long that the international-ness is no longer notable to the people who live there.
The Dutch side has the marina infrastructure that the sailing fleet uses: the Simpson Bay Lagoon is one of the finest natural hurricane holes in the Caribbean and the bridge that controls access to it from the sea is the specific passage that every visiting yacht knows from the planning chart before it knows it from the helm. The French side has the food: the specific quality of the French Caribbean cuisine that the island’s Gallic half produces in the restaurants above the beaches that the Sint Maarten cruising guide describes with the reverence that the French Caribbean gastronomy deserves.
The Naora voyage arrives at Sint Maarten in the Caribbean chapter as the boat that has been at sea since Bodrum and that has crossed the Atlantic in the weeks before the Caribbean landfall. The first Caribbean island is always the island of the Atlantic arrival, and the specific quality of the first land after 2,700 miles of the open Atlantic is a quality that Sint Maarten has been providing to the westbound Atlantic crossing fleet for as long as the Atlantic crossing fleet has been crossing.
If the first Caribbean island is Sint Maarten and the Heineken Regatta is beginning when the boat arrives, the coincidence is the kind of coincidence that the offshore sailing life produces with a frequency that the non-sailor would consider improbable and that the sailor knows as the normal operation of the calendar that the sailing world has been organising around the same wind systems and the same seasonal patterns for generations.
The Decision We Have Not Yet Made
We have not confirmed participation in the Heineken Regatta 2028. The five-year circumnavigation is planned around the offshore passages and the offshore destinations that the route identifies as the primary content of the voyage, and the Heineken Regatta is an event that the Caribbean chapter passes close to rather than an event that the route was planned around.
The decision to enter depends on the specific sequencing of the Caribbean legs in late 2027 and early 2028, on the condition of the Eighty2 after the Atlantic crossing, and on the specific conversation with the Naora Circle members who will be aboard in the first week of March 2028 about whether the regatta is the Caribbean experience they want to be part of.
What I can say is that the memories are good. That the event is one of the things the offshore sailing calendar produces that deserves its reputation. That in March 2028 we will be in the Caribbean, the Heineken Regatta will be in Sint Maarten, and the specific quality of the event and the specific quality of the Naora voyage in the Caribbean chapter are compatible in the way that two things are compatible when they share the same values about what the sailing life is for: the competition that is worth taking seriously and the fun that is worth taking equally seriously, in the water and conditions that the Caribbean provides at its best.
One thing is certain: we would never approach Naora as a racing platform. The purpose of this journey is far too important to compromise for competition. Racing inevitably introduces unnecessary pressure, risk, and unpredictability. Factors that could jeopardize the rhythm, safety, and continuity of the expedition itself.
Naora is designed around a very different philosophy. It is about moving through the world deliberately, safely, and with intention. Protecting the experience, the people on board, and the integrity of the journey will always come before speed or performance.
If you are considering the Caribbean leg of the Naora voyage in early 2028 and the prospect of the Heineken Regatta as a possible chapter of that leg is part of the appeal, the conversation with Antony is where the current planning status and the specific leg sequencing that makes it possible or not is most accurately described. The regatta is on our radar. The radar is pointing at Sint Maarten in March 2028. What happens at that position in the route is a story we are still writing.
