Luxury Catamaran Private Day Sail from St. Maarten to Anguilla

Imagine slipping into your flip-flops, stepping onto a sleek, brand-new Lagoon 42 catamaran, and heading out onto the calm Caribbean waters. That’s exactly the kind of experience this Luxury Private Day Sail offers—a smooth, luxurious cruise from St. Maarten to the serene island of Anguilla. Whether you’re celebrating a special occasion or simply craving a day away from crowded beaches and busy streets, this trip promises a blend of comfort, beauty, and personalized service.

Two standout features we love: first, the all-inclusive nature of the trip—think gourmet meals, premium drinks, and plenty of water toys—all served with a friendly crew that treats you like a guest rather than a just another booking. Second, the luxury vessel itself, a 2022 Lagoon 42 designed for comfort and style, making every moment on deck feel like a private yacht experience.

That said, a possible consideration is the price point—at nearly $700 per person, this isn’t your average day trip. But for those seeking top-tier service, privacy, and an upscale experience in the Caribbean, it’s a sound investment. This tour works best for travelers who appreciate comfort and are willing to indulge a little, especially couples, families, or groups celebrating something special.

Key Points

• Luxury vessel: Modern Lagoon 42 catamaran with all the comforts
• All-inclusive indulgence: Gourmet meals, premium drinks, water toys
• Personalized service: Dedicated captain and crew catering to your needs
• Beautiful scenery: Cruising along Anguilla’s coastline with crystal waters
• Flexible itinerary: Stops for swimming, snorkeling, and exploring beaches
• Highly rated: Consistently perfect reviews and strong recommendation rate

An In-Depth Look at the Experience

Starting Point and What to Expect at the Dock

The adventure begins at Port de Plaisance Yacht Club in Cole Bay, on the Dutch side of St. Maarten. The check-in process is straightforward—you’re welcomed aboard with a cool scented towel and a decadent handmade chocolate, which sets the tone for the day. After a brief safety briefing and tour of the vessel, the crew—comprising an experienced captain and attentive staff—takes over, ensuring you’re comfortable and ready for the journey ahead.

The Journey to Anguilla

Once underway, the real magic begins. The 9-hour trip is designed to maximize relaxation and enjoyment. You’ll love the way the crew keeps the mood light with chilled drinks, including a sparkling mimosa in hand as you settle into the luxurious lounge areas. The spacious teak deck invites you to stretch out, sip your drink, and soak in the vistas of Anguilla’s shoreline.

The boat boasts a floating lily pad, paddleboards, snorkeling gear, and other water toys, so you can get active or just float lazily in the clear Caribbean waters. The trip to Anguilla is around 8 hours—plenty of time to explore, swim, and enjoy the scenery. The route along the coast offers superb photo opportunities, with the coastline’s rugged beauty and pristine beaches providing a perfect backdrop for your day.

Highlights of the Itinerary

• Stop at Princess Port de Plaisance:

The trip kicks off with a brief 30-minute stop at this marina, where a quick safety briefing and orientation are provided. It’s a convenient starting point with modern amenities, so you’re well-prepared for the hours ahead.

• Cruise to Anguilla with gourmet snacks:

As you sail, enjoy breakfast items like fresh fruit, artisanal cheeses, and French pastries, paired with your choice of beverages. Many reviewers note the delicious food—from barbecued skewers to homemade cookies and locally made ice cream—that makes the trip feel indulgent.

• Time on Anguilla’s beaches:

Once in Anguilla, you’ll have time to swim, sunbathe, or explore the island’s famous beaches. Many reviewers highlight the crystal-clear waters and the tranquil, uncrowded beaches, perfect for relaxing or snapping memorable photos.

• Return journey via Simpson Bay Bridge:

The trip wraps up with a scenic cruise back through the bridge, where you can wave to onlookers, before docking at the starting point. The 30-minute return leg offers a final chance to unwind and reflect on the day.

Included Amenities and What They Mean for You

This tour doesn’t just offer a boat trip; it’s a curated experience emphasizing comfort and convenience:

• Gourmet food: Breakfast with fresh fruit and French pastries, plus barbecue skewers and homemade cookies.
• Premium drinks: An open bar with craft cocktails, mocktails, beer, wine, prosecco, and infused water keep everyone refreshed.
• Water toys: Paddleboards, snorkel gear, and a lily pad mat add fun options for active guests.
• Sun protection: Reef-safe sunscreen and towels are provided, so you can relax without worrying about skin protection.
• Private experience: Only your group participates, ensuring exclusivity and personalized service.

Value and Price Considerations

At $698.75 per person, this trip isn’t cheap. However, considering the inclusions—luxury vessel, gourmet food, unlimited drinks, water toys, and attentive crew—the value becomes clearer. Many reviews describe it as “worth every penny,” and the all-day indulgence is perfect for those wanting a premium experience without the hassle of planning.

The Crew and Service

Reviewers are unanimous in praising the crew, especially Captain Andre and Diane, for their warm hospitality and professional service. From the moment you board to the final wave goodbye, they treat you like friends, making the day both special and relaxed. This personal touch enhances the overall experience, making it more than just a boat ride.

Practicalities and Tips

• Booking: The trip is popular, booked about 80 days in advance on average, so plan ahead if you want a spot.
• Duration: Be prepared for a full day—starting at 8:00 am and returning around 5:30 pm.
• Weather: The tour is weather-dependent; if conditions aren’t suitable, you’ll be offered a different date or a full refund.
• Age restrictions: You must be 18+ for alcohol consumption.
• Transportation: No hotel pickup or drop-off included, so plan to arrive at the meeting point in Cole Bay.
• What to bring: Sunscreen, a hat, swimwear, and a sense of adventure.

Who Will Love This Tour?

This experience is perfect for travelers who want to indulge in luxury without sacrificing authenticity. It suits those celebrating a special occasion, couples seeking an intimate day at sea, or groups looking for a private, all-inclusive escape. If you appreciate good food, excellent service, and stunning scenery, this sail is likely to exceed your expectations.

The Sum Up

This private day sail from St. Maarten to Anguilla offers an upscale, well-organized, and deeply enjoyable way to experience the Caribbean. With its modern vessel, attentive crew, and delicious food and drinks, it’s a fantastic option for those prepared to spend a little more for a memorable day on the water. The relaxed pace, combined with spectacular views and water activities, makes it an excellent choice for anyone wanting a taste of luxury and local beauty.

While the price might seem steep, the amount of comfort, personalized service, and premium amenities included make it an attractive value for travelers seeking a special, hassle-free day. If you’re dreaming of sailing in style, this trip hits all the right notes.

FAQ

Is there a minimum age for this tour?
Yes, the minimum age for alcohol consumption is 18, but most travelers of all ages can participate in the cruise and water activities.

Are there water toys available onboard?
Absolutely. You’ll have access to paddleboards, snorkeling equipment, and a lily pad mat, perfect for relaxing or playing in the water.

What is included in the meal and drinks?
A variety of gourmet foods, including breakfast, barbecue skewers, homemade cookies, and locally made ice cream. The bar offers craft cocktails, mocktails, beer, wine, prosecco, and infused water.

Is the trip suitable for families or children?
Most travelers can participate, but the alcohol policy restricts ages 0-17 from drinking. Families with children should consider the overall experience and water activity levels.

How long is the trip?
The total duration is approximately 9 hours and 30 minutes, with about 8 hours spent cruising and exploring Anguilla.

Where does the tour start and end?
It begins at the Port de Plaisance Yacht Club in Cole Bay and returns there at the end of the day.

Is gratuity included?
No, gratuity is not included and is at your discretion based on the crew’s service.

Do I need to book in advance?
Yes, it’s recommended to book about 80 days ahead, especially during peak seasons.

What happens if the weather is bad?
The tour may be canceled or rescheduled due to poor weather. If canceled, you’ll be offered a different date or a full refund.

This private cruise offers more than just a boat trip—it’s a carefully curated day of luxury, relaxation, and Caribbean beauty. Perfect for those who want to indulge in comfort while exploring some of the region’s most stunning waters and beaches.