Serious Fun at the St. Maarten Heineken Regatta

Sint Maarten, Heineken Regatta, 2023, Race Day 1, Thursday

By Allegra Smith-Herriott

As the plane started its descent, bright blue skies gave way to crystal clear turquoise waters as we skimmed over the famous Maho Beach. Exiting the airport, I was hit with a wall of warm salty air from the northeast trade winds. Nothing compares to arriving in the Caribbean.

From the airport, I headed to the Regatta Village in Port de Plaisance. Wednesday being ‘Day 0’ was registration day of the Regatta. Teams were out on the water to shake out sails, on the docks making last-minute preparations and in the Regatta Village for registration and most importantly picking up their cases of Heineken.

Regatta Green Zone party © Souleyman T. Photography

I was welcomed at the sustainably built bar with an icy cold refreshment to enjoy the vast open-air space and get myself registered. Nearing the end of the day, the Village was winding down with a few stragglers enjoying their complimentary Heineken, but most sailors were back on their boats in preparation for Day 1. It was a nice, serene atmosphere, a direct contrast of what the next few days would bring.


The St. Maarten Heineken Regatta is one of the world’s best sailing competitions and the largest regatta in the Caribbean. The event includes four days of world-class racing and four days of world-class partying. All in a picture-perfect setting. The regatta takes place in Port de Plaisance, a gateway to Simpson Bay where all of the action happens out on the water each day.

Sint Maarten, Heineken Regatta, 2023, Race Day 4, Sunday, March 5
Volvo fleet racing past a watch boat © Laurens Morel

The event has a strong international appeal and draws sailors from all around the world. Teams travel not only by plane but many by boat, some clocking close to 3,500 NM trans-Atlantic. The 43rd annual St. Maarten Heineken Regatta hosted over 100 boats from all around the world, including many Canadian teams.

© Souleyman T. Photography


It was a bright and early start on Thursday morning, the official first day of regatta racing. Boats started casting off the dock full of anticipation to head out into the open waters for some pre-race practice. Based on the conditions, different racecourses were called by the Race Director and relayed to the teams along with the staggered start times for each fleet. Soon it was time to climb into a media boat and head out to watch the action.

It was an ultimate day for racing with strong winds as we bobbed in and amongst the boats tacking and gybing all around us. We took up position directly beside the start boat as the clock neared the top of the hour. And then it was time for the Volvo fleet to start.

Sint Maarten, Heineken Regatta, 2023, Race Day 4, Sunday, March 5
Nauti Canucks from the Bareboat division © Laurens Morel

It was choreographed mayhem with 65-to-70-foot boats running parallel to the start line in anticipation of the gun. It was windy, and wavy. Sailors were yelling, boats creaking under tension, people cheering and then the gun sounded. If I reached out my hand far enough, I could have touched a 70-foot Volvo barrelling across the start line right in front of me. Before we knew it, they were out of sight and the next fleet was getting ready for their scheduled start.

After an amazing day on the water with near-perfect conditions chasing the fleets, sailors crossed the finish line and made their way back to the docks for a short breather. The fun was just getting started.

Sint Maarten, Heineken Regatta, 2023, Race Day 3, Saturday, March 4, Round The Island, Panacea
Panacea in full race mode © Laurens Morel

The Regatta Village officially opened at 15:00 every day. It was a constant stream of sailors as they made their way to the Village to enjoy their choice of complementary beverage to celebrate the day’s success; Heineken, Veuve Clicquot, Tito’s or Fiji water. Thousands of locals and tourists joined in on the fun as well.

Daily prize giving happened at 18:00 every day until local artists took to the main stage to perform for the rest of the night. And the fun didn’t stop there. Every night were Green Zone parties at top venues around the island. Starting at 22:00, you could stay up until sunrise giving you just enough time until you had to be out in Simpson Bay at 10:00 the next morning for the first race start.


Day 3 was the around the island race and I was lucky enough to climb aboard Canadian team Bella J for the day. This J/133 travelled over 2000 NM to the Caribbean from Halifax, Nova Scotia. The friendly crew of 13 made for a thrilling 32 NM race with great winds and lots of liquid sunshine. Being out on the water in a first-hand race setting showed what a great mix of sailors take part in this regatta. The opportunity to compete against professional teams puts your skills to the test no matter how much fun you had the night before.

Bella J crew
Bella J crew

There were two Canadian Bareboat entries that were there for the sailing but just as much there for the fun; Team Nauti Canucks and Team Asterias. The combination of a low participation fee and a boat charter option created opportunity for everyone to join in on the Serious Fun the Regatta has to offer. Canadian teams Panacea and Salacia 1 both keep their boat in the Caribbean to attend these Regattas. This was Panacea’s first time doing a charter boat concept. Teams Little Wing and Imaginaire also flew down for some racing and vacationing.

Sailors continually commented how one of the best parts of the Regatta is the comradery it brings. There’s no shortage of fun both on and off the water; not to mention the acclaimed bridge show! The Regatta also generates a positive economic impact and makes a strong effort to give back to the island.

Sint Maarten, Heineken Regatta, 2023, Race Day 3, Saturday, March 4, Round The Island
Around the Island Race © Laurens Morel

A unique aspect of the SMHR is their initiative of highlighting key values each day of the event. Day 1 was all about sustainability. For every regatta entry, one new mangrove was planted in St. Maarten. Day 2 highlighted the Next Generation and youth sailors from the Sint Maarten Yacht Club competed in their own races in Simpson Bay. Women stole the show on Day 3. Not only is Michele Korteweg the youngest woman to ever become race director, but women dominated the fleets like team Purple Mist from the UK and team Something Hot, Heineken’s women-only crew! Day 4 was the grand finale and celebrated talent. Grammy award-winning artist Koffee took to the main stage to end off the Regatta with a bang.


The following day I said my goodbyes and the plane took off over a sea of sailboats. Many sailors were departing the island, but many were lucky enough to stay for some recreational sailing or were making their way to the next Caribbean Circuit Regatta.

Team Asterias
Team Asterias

The SMHR hosts sailors from more than 25 countries from professionals on monohulls and performance multihulls to Bareboat vacationers and Caribbean cruisers. Whether you sail your own boat, join a crew, charter a boat for a week, volunteer or simply attend as a tourist, the opportunities to participate are endless. Serious Fun is the motto of this regatta and there’s no doubt you’ll experience just that.

Save the date! The 44th edition of the SMHR is February 29 – March 3, 2024. Get your crews in order and sign up for this bucket list Caribbean regatta! For more information, visit heinekenregatta.com.


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