Heineken Regatta 2027: What Regatta Week Means for Owners and Buyers

The 47th St. Maarten Heineken Regatta will run from March 4 to 7, 2027, based in Simpson Bay. Registration is open, and charter berths are already on offer. For four days the island fills with crews, supporters and spectators, and every bed near the lagoon is in demand.

If you own a rental in Sint Maarten, this is one of the weeks that makes your year. If you are thinking of buying, it is one of the best weeks to see the island at full speed.

The event in brief

The Heineken Regatta is the largest regatta in the Caribbean and one of the best known in the sailing world. Its motto is "Serious Fun", and it lives up to both halves.

• Dates: March 4–7, 2027.

• Base: Simpson Bay, with the Regatta Village at Princess Port de Plaisance. Entry to the village is free, with music and food every evening.

• The fleet: more than 100 boats from over 35 nations took part in 2026, from maxis and performance multihulls to bareboat charters and one-design classes.

• The crowd: organisers put attendance at more than 20,000 visitors a year.

The 2026 overall win went to a local team, More Zessin', racing a J/105. That says a lot about the event: professional crews and island sailors race on the same water.

Why regatta week matters for rental owners

Early March is already high season. Regatta week stacks a second wave of demand on top: crews who need beds close to the start line, owners and sponsors who want something better than a crew house, and spectators who plan their holiday around the parties.

A few things we tell owners every year:

• Open your calendar early. Crews often book months in advance, once their entry is confirmed. If your March dates are still closed in the autumn, you are missing the first wave.

• Price the week, not the month. Do not apply your standard March rate. Look at what comparable units near the lagoon actually booked for the last regatta.

• Set clear rules. Crews are usually good guests, but they are groups. Be explicit about occupancy limits, parking and noise, and collect a proper deposit.

• Location decides. Simpson Bay, Cole Bay and Maho are within easy reach of the village and the lagoon. The further you are, the more your listing has to explain how guests get there.

If you would rather hand this to a team that does it every day, see our rental management service.

Why buyers should come in regatta week

Visit in low season and you see a quiet island. Visit in regatta week and you see how it works at its busiest: traffic on Airport Road, restaurants in Simpson Bay, the bridge openings, the noise level at night. That is useful information before you buy.

It is also a practical week. You can see how much demand exists for rentals near the lagoon, talk to owners, and view property in the same trip. If you plan to come, tell us in advance and we will line up viewings around the racing.

What to keep in mind

Regatta week is a strong week, not a business plan. A rental should make sense across the whole year, including the quieter months. We wrote about how arrivals shape demand in our analysis of the 2026 tourism figures.

Questions we get

When is the 2027 Heineken Regatta? March 4 to 7, 2027, based in Simpson Bay. It is the 47th edition.

Is the Regatta Village open to the public? Yes. Entry is free, with live music and food in the evenings.

When should I open my calendar for regatta week? As early as possible. Registration is already open, and crews start looking for accommodation once their entry is confirmed.

Is regatta week a good time to view property? Yes, if you want to see the island at its busiest. Book viewings in advance, as agents and owners are busy too.

Sources: St. Maarten Heineken Regatta, 2027 registration announcement and event information; attendance figure as stated by the organisers.