• Wave icon Trip Type: Coastal
  • Speech bubble icon Instructors: 2
  • People icon Crew Size: Max 9 (10 for ocean)
  • Cake icon Ages: 18-70 ish
  • Pin icon Region: Caribbean & The Americas

Adventure Rating:


Experience Required:

10 Days from £2,499

Dates, Prices & Travel

Join the crew for St Maarten Regatta

The St. Maarten Heineken Regatta is serious fun, with a wonderful blend of friendly competition and Caribbean festivities. It’s much more than just a sailing regatta; it’s also a celebration of the music and culture of the island (also called Sint Maarten). The event, which is the largest regatta in the Caribbean offers world-class racing in crystal-clear waters. Competitors range from Olympic medalists to enthusiastic amateurs, all drawn by the thrill of sailing and the event’s unique spirit.

The regatta is renowned for its warm trade wind sailing conditions, fun courses, and the camaraderie among participants and party goers. Post-race, crew can enjoy great local food and enjoy a cold beer in the Regatta Village. The island then transforms into a big party. Each night is a lively mix of local events and world-class entertainment, featuring live music, dancing, and spectacular beach parties. Past events have seen bands such as the Black Eyed Peas, UB40, Wyclef Jean, and The Commodores. It’s this blend of competitive sailing and beachside entertainment that makes this event so uniquely appealing.

Race with Confidence: Join the Rubicon 3 Team for a Safe, Supportive, Thrilling Adventure

Racing with Rubicon 3 is famously friendly and inclusive, with crew comfort and confidence as our top priorities. Perfect for beginners and seasoned sailors alike, our approach is designed to ease all your concerns about yacht racing.

  1. Tailored Training: Our experienced skippers provide comprehensive training, ensuring you gain the skills and confidence needed, regardless of your starting level. We focus on a step-by-step approach, making yacht racing accessible and enjoyable for everyone.
  2. Emphasis on Safety: Your safety is paramount. As well as our world-class safety protocols, we conduct thorough safety briefings and drills. You’ll learn how to handle various scenarios while racing, significantly reducing the risks and anxiety.
  3. Physical Fitness Not a Barrier: Our team values strategy and teamwork over physical prowess. Roles on the yacht are assigned based on your comfort level and ability, ensuring everyone can participate and contribute effectively.
  4. Supportive Team Environment: Rubicon 3 is a welcoming community where camaraderie is critical. We believe in teamwork, mutual support, and enjoying the experience together. You’ll never feel out of place or under pressure to perform.
  5. Guided Introduction to the Sport: We demystify yacht racing with clear explanations and hands-on experiences. Learn at your own pace in a stress-free environment, turning the unknown into a thrilling adventure.

Join us for a unique opportunity to take part in yacht racing in a safe, supportive, and fun setting.

Want to join?

Go to the Dates & Prices button to see the dates this trip runs. It will also give you information on connecting travel, including where to fly and when and where to join the boat.

Sailing Area

st maarten regatta race area map
st maarten regatta race map
The Yachts
Key Information
What’s included
  • All food and accommodation on board

  • All fuel & berthing fees

  • Your own bunk and storage area

  • Use of oilskins

  • Use of lifejacket

  • Sailing tuition

  • RYA Competent Crew (supplementary fee)

What’s Not included
  • Your connecting travel to & from boat

  • Sailing & travel insurance

  • Meals you choose to eat ashore

  • Alcohol

  • Visas where required

  • Discretionary tip

Interested in dates & availability?

To see when this trip runs, its start and end locations, price to join the crew and availability, click on the ‘Dates, Prices & Travel’ button up top.

Discretionary tipping of the Rubicon 3 crew

The trip price is 5% less than we would normally charge. This is to allow you at the end of your adventure to offer a combined 5-10% tip to the Rubicon 3 skipper and mate if you feel they have delivered exceptional performance. This tip is entirely discretionary. See our FAQs here.

Got some questions?

Joining a big sailing adventure is a big thing, so don’t be surprised if you have lots of questions before you book. Who else joins, what to expect, and so many more queries are entirely normal. The home page has loads of info on this (scroll to the bottom), there are our FAQs and never hesitate to contact us by email, phone or live chat. The team are here to have a chat, discuss options, answer questions and help make sure you get on the exact right sailing trip for you.

The St Maarten Regatta takes place over four days. To ensure you have the best experience, we include a pre-race sail from Antigua, two days of pre-regatta training, and a couple of days to sail back to Antigua afterward, giving you some more relaxed time to enjoy the island and sailing.

Join the boat in Antigua

We’ll start with all the safety briefings and yacht acclimatization you’d expect with Rubicon 3. A really thorough start helps ensure everyone stays safe but also that everyone can get fully involved. We’ll head out on the water in the afternoon and get the rust out of the system, polishing your individual skills and starting to shape you into a regatta-ready team!

Sail to St Maarten

Next, we’ll set sail for St. Maarten, which is around 150 miles north of Antigua. This gives us a full day of sailing in the powerful trade winds and perfect training, followed by a special night of sailing under the stars and memories for life. On arrival into Antigua the next day, you’ll find the crew have bonded and are operating really well as a team.

Pre Regatta Training

Next, we’ll be conducting training drills off the coast of St. Maarten, discussing and fine-tuning racing techniques.

Sail Trim and Boat Handling

  • Practice adjusting sails for optimal speed and efficiency, considering wind and sea conditions.
  • Drill on tacking and gybing, focusing on smooth, coordinated maneuvers.
  • Work on upwind and downwind sailing techniques, including spinnaker handling if applicable.

4. Starting Line Procedures

  • Practice timing and positioning for race starts.
  • Execute simulated starts to understand the importance of positioning and timing in relation to other boats.

5. Race Tactics and Strategy

  • Discuss race strategy, including course navigation, identifying shifts in wind, and tactical positioning relative to other boats.
  • Practice mark rounding, focusing on efficient turns and maintaining speed.

6. Crew Communication and Coordination

  • Emphasize clear, effective communication among crew members.
  • Practice rapid, coordinated responses to changing conditions and commands.

7. Safety Drills

  • Conduct man-overboard drills and other safety procedures.
  • Reinforce the importance of safety gear and protocols during racing.


  • Racing is sponsored by the Caribbean Yachting Association with the cruising boats rated under the St. Martin handicapping system

St. Maarten Heineken Regatta

Each of the four race days follows a similar structure:

  • Morning: Briefing and preparation for the day’s races.
  • Day: Participate in the race events.
  • Evening: Enjoy the regatta festivities, including live music, parties, and local events, including the legendary closing party

Return Sail to Antigua

Early the next morning, we’ll depart St. Maarten for Antigua. We’ll enjoy a more relaxed sail back, sharing experiences and learnings from the regatta. It’s always a very special sail. On arrival in Antigua, there’ll be a final dinner with the crew, sharing memories and saying farewells before disembarkation and goodbyes as the crew depart for home or continue their travels.


The difference between Rubicon 3 and a yacht charter

This is not a luxury yacht charter vacation on a private yacht but a proper sailing adventure. 

  1. Tailored Experience: Unlike many yacht charters, the Rubicon 3 team works daily to tailor the experience to your interests and skill level. Whether you’re interested in learning advanced sailing techniques, exploring off-the-beaten-path destinations, or focusing on particular activities like snorkeling or fishing, we look to help you achieve it.
  2. Expert Knowledge: Yacht charter companies will send you off with minimal instruction. Rubicon 3 has extensive local knowledge and expertise. We can find hidden gems, secluded anchorages, and the best spots that might be off the radar of the charter companies. This insider knowledge significantly enhances the sailing adventure. 
  3. Learning Opportunities: Racing with Rubicon 3, you don’t need any previous sailing experience. If you’re interested in learning about sailing, navigation, or seamanship, the expert Rubicon 3 instructors ensure a hands-on, educational experience. This is ideal if you see your sailing trip as a vacation and a learning opportunity.

Dates, Prices & Travel

Start Date & Location

March 4, 2025

End Date & Location

March 13, 2025






Join Waitlist

Trip Information

Start Date: March 4, 2025

Start Time: 09:00

Start Country: Antigua

Start Port: Antigua

Start Marina: Jolly Harbour

End Date: March 13, 2025

End Time: 10:00

End Country: Antigua

End Port: Antigua

End Marina: Jolly Harbour

Find Flights For This Trip
Fly Into: Antigua (IATA Code: ANU)
Fly Out of: Antigua (IATA Code: ANU)

* Flights are not included in the trip price.

Important Notes
Joining the boat
  • You will join the boat in Antigua.
  • It is scheduled to be in Jolly Harbour, Antigua.
  • The trip starts at 9:00 AM on March 04 2025, so you will need to be in Antigua by March 03, 2025.
  • You have two options for accommodation on the night before the start date:
    • Stay in a hotel or AirBnB in Antigua.
    • Alternatively, you can stay onboard the boat from 6:00 PM on a bed & breakfast basis. Select this option during your booking process.
Leaving the boat
  • You will leave the boat in Jolly Harbour, Antigua
  • The boat is scheduled to arrive into Antigua on the evening of March 12, 2025, and you will need to disembark by 09:00 March 13 2025.
General Notes
  • We have a very strong track record of meeting the scheduled end date, with only a few exceptions over a decade of sailing and across hundreds of thousands of miles of sailing. However, given the nature and distance of ocean crossings, we can’t guarantee it and recommend booking flexible onward travel from Antigua or at least allowing an extra day in your itinerary as a precaution.
  • You cannot stay on the boat after the trip end date.
  • Once you have booked, we will connect you up with other crew so you can liaise regarding connecting travel, meet up in advance etc.
  • If you have any questions, don’t hesitate to get in touch.
5-Point Pre-Booking Checklist

Before you finalize your booking, we suggest you run through our pre-booking checklist:

  1. Check Flights: Make sure you have found the right flights for your trip. Book them as soon as you have booked your Rubicon 3 trip.
  2. Travel Insurance: Once you’ve booked your trip with us, buy some sailing travel insurance. Read our full guide here.
  3. Passport Validity: Ensure your passport is valid for at least six months beyond your planned return date. Some countries require this for entry, so it’s crucial to check and renew your passport if necessary.
  4. Visas: Most sailors will not require any visas for this trip. However, if you are concerned, check any visa requirements for both your destination and any transit countries. If you do need a visa, processing times can vary, so it’s advisable to apply well in advance of your trip.
  5. Vaccinations and Health Checks: There are no vaccinations required for this trip. Make sure you have an acceptable level of fitness and agility. You can read our guide here. This is for the safety of all on board.

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