Heineken Regatta 2027: Dates, Schedule and How to Join the Caribbean's Biggest Sailing Event

Date of the event: March 4 - March 7, 2027 (always takes place in early March)
Location: Sint Maarten, Caribbean

Source: the official St. Maarten Heineken Regatta website.

Quick answer

The 47th St. Maarten Heineken Regatta runs from Thursday, March 4 to Sunday, March 7, 2027 in Simpson Bay, Sint Maarten. It is the largest regatta in the Caribbean, with four days of racing and free evening entertainment in the Regatta Village under the motto "Serious Fun". You can join with your own boat or a chartered yacht. Tubber arranges the yacht and the details, so you only have to step aboard.

Heineken Regatta 2027 at a glance

• Dates: March 4 to 7, 2027 (registration Wednesday, March 3)
• Location: Simpson Bay, Sint Maarten (Saint Martin), Caribbean
• Organizer: Sint Maarten Yacht Club Regatta Foundation, title sponsor Heineken
• Fleet (2026): 113 boats from 38 nations (record: 284 boats in 2008)
• Visitors: 20,000+ per year from 37+ countries
• Regatta Village: Free entry, opens 4 p.m., live entertainment from 7 p.m.
• Spectator boat: March 6 and 7, 7:30 a.m. to 12:30 p.m., US$125 (food and open bar included)
• Airport: Princess Juliana International (SXM), a short drive away

What to expect

The regatta started in 1980 with just 12 boats and has grown into the Caribbean's flagship sailing event. Early March brings steady trade winds, warm turquoise water and sunshine, and it can get lively: the final day of 2026 saw gusts above 35 knots. The Regatta Village in Simpson Bay is the heart of the action, with live music, food, drinks and the chance to mingle with world class sailors. Whether you chase victory or just want to feel the Caribbean's most iconic regatta, there is a place for you.

Schedule

• Wed, March 3: registration, 8:30 a.m. to 6 p.m.
• Thu, March 4 to Sun, March 7: four race days, first warning signal at 9:40 a.m. in Simpson Bay. Daily prize giving from 6 p.m., live entertainment from 7 p.m. (final prize giving on Sunday from 6:30 p.m.).
• Sat, March 6: Diam 24 beach stadium racing in Grand Case from 11 a.m.
• Daily: Bridge Show at the Sint Maarten Yacht Club, with boats passing the Simpson Bay Bridge at 8:30 a.m., 3 p.m. and 5 p.m.

Schedules can change, so check the official schedule before you travel.

Racing, classes and ratings

Entrants range from Olympic medalists on Maxis and performance multihulls to holiday-makers on chartered bareboats. Racing monohulls sail eight races over four days, cruising and multihull classes get their own courses, and the fast Diam 24 trimarans form an exciting one-design class. The Island Time class offers one relaxed, medium-length race per day, perfect for cruisers and newcomers.

All classes except Island Time need a CSA (Caribbean Sailing Association) rating. Here is the twist: a lower rating can win you the race. The lower your yacht's rating, the less time is added to your sailed time. A furling mainsail gives a lower rating than a fully battened one, so charterers often choose accordingly. Choosing wisely can be the difference between an average finish and the podium.

How to join (with or without your own boat)

You can bring your own yacht or charter one with friends. Racers register through the official page on YachtScoring, where you can also read the Notice of Race.

Want a hassle-free way to join? Your Personal Shipmate at Tubber finds the right yacht and takes care of the details. Request a free quote or browse our yachts in Saint Martin and the wider Caribbean.

Included in a Tubber regatta package

• Regatta entry fees and a welcome cocktail
• Local race support before and during the event
• Yacht preparation and cleaning, including hull cleaning
• Official yacht measurement and a pre-race briefing

Not included

• Flights and local taxi transfers
• Cruising taxes, departure taxes and mooring fees
• Provisions and drinks on board
• Spinnakers, poles or cruising chutes (not available in the Caribbean)
• Delivery costs, and tickets for official events around the regatta

Parties and spectator experience

The nightly parties are as famous as the racing. The Regatta Village is free and open to the public, with international and local artists, creative costumes and concerts popping up all over the island. Picture dancing under the stars with an ice cold Heineken in hand and music drifting through the warm Caribbean night.

Prefer to watch? Book a seat on the official spectator boat (March 6 and 7, via the official booking site) for a front-row view of the racing. The regatta is family-friendly, with activities for all ages.

Why sailors love St. Maarten

Half Dutch, half French and full of adventure: St. Maarten mixes Caribbean charm with European flair. Sail from exhilarating open water racing to relaxed island hopping, then explore rainforest, white sand beaches and hidden caves onshore. The Sint Maarten Yacht Club, next to the Simpson Bay Bridge, is the lively gathering place of the local sailing scene.

Other Caribbean regattas

• Golden Rock Regatta: a friendly bareboat event starting in St. Maarten, with socials across several Windward Islands.
• BVI Spring Regatta: March 29 to April 4, 2027 at Nanny Cay, Tortola. See yachts in the BVI.
• Antigua Sailing Week: famous for excellent racing and legendary parties. See yachts in Antigua and Barbuda.

Future dates

The regatta always takes place around the first weekend of March: 2028: March 2 to 5, 2029: March 1 to 4, 2030 (50th anniversary): March 7 to 10.

Why book early?

The Heineken Regatta sells out every year. The best yachts and accommodations go first, flights to Sint Maarten fill up fast and prices rise as the event approaches. Booking early gives you the widest choice, the best rates and a stress-free start.

Frequently asked questions

When is the Heineken Regatta 2027?

From Thursday, March 4 to Sunday, March 7, 2027, with registration on Wednesday, March 3.

Can I join without owning a boat?

Yes. You can charter a yacht with friends. Tubber can organize this for you.

Do I need racing experience?

No. The Island Time class offers one relaxed race per day and does not require a CSA rating.

Is the Regatta Village free?

Yes. It is free and open to the public. The spectator boat and VIP experiences are ticketed separately.

How many boats take part?

The 2026 edition had 113 boats from 38 nations. The record is 284 boats, set in 2008.

How do I get there?

Fly into Princess Juliana International Airport (SXM), a short drive from Simpson Bay. Flights fill up fast, so book early.

Ready to go the extra mile?

With verified yachts, the best price guarantee and your own Personal Shipmate, you will be sailing in no time. Get in touch for a custom offer and we will plan your perfect regatta getaway.