Unforgettable Day on a Private St. Maarten Sailboat Charter!

Let me tell you, folks, there’s nothing quite like chartering a private sailboat in St. Maarten. It’s the epitome of a luxurious escape, a chance to ditch the crowds and create memories that will last a lifetime. Recently, I had the pleasure of experiencing this myself with Random Wind Charters, and let me tell you, it was pure magic.

Escape the Ordinary: A Day Designed for You

The beauty of a private charter is that it’s entirely on your terms. Unlike those crowded group tours, you’re the captain (well, almost)! From the moment we booked, Random Wind Charters was incredibly accommodating. We opted for a full-day excursion, but they offer flexibility – shorter sails or even multi-day adventures are on the table. We also pre-arranged a delicious vegetarian lunch, which was a delightful touch (and trust me, their veggie options are no afterthought!).


Let a crew take care of the day’s itinerary for you on a private catamaran charter off the coast of St. Maarten, with stops at secluded areas far from the crowds of Philipsburg. In addition to an open bar, enjoy a homemade lunch prepared on board and unlimited use of snorkeling gear, kayaks, and paddleboards. Unlike large group tours, a private charter offers an intimate, tailored experience.

  • Excellent value for money
  • Ideal choice for families
  • Small group ensures personal service
  • Free drinks included
  • Lunch included
  • Private tour is operated with just your party and a guide/driver
Private Sailboat Charter in St Maarten

Setting Sail: Embracing the Caribbean Breeze

Our adventure began in the picturesque Simpson Bay. The crew – a friendly and professional bunch – greeted us warmly and ensured we were comfortable aboard the beautiful catamaran. As we set sail, the Caribbean breeze played through our hair, and the turquoise waters stretched endlessly before us. The feeling of leaving the everyday behind and surrendering to the rhythm of the ocean was pure bliss.

Simpson Bay itself is a sight to behold, a perfect gateway to the wonders of the Caribbean Sea. As the catamaran glided gracefully through the water, the scenic coastline of St. Maarten unveiled itself, a tapestry of lush green hills and sparkling blue waters. The tranquil beauty of the surroundings set the tone for an extraordinary day ahead.

Snorkel Among Vibrant Coral Reefs

Our first stop was a hidden gem – a secluded cove teeming with marine life. Donning the provided snorkel gear, we plunged into a world of vibrant coral reefs and colorful fish. It was like swimming through an underwater kaleidoscope! The crew was fantastic at pointing out interesting marine creatures and ensuring everyone felt safe and comfortable exploring the underwater world.

The cove we visited is one of St. Maarten’s best-kept secrets, an underwater paradise that few get to experience. Schools of tropical fish darted through the coral, while graceful rays glided by. The water was so clear that every detail of this underwater wonderland was visible. It was an unforgettable experience, a chance to connect with nature in its purest form.

Thrills and Chills: Tarzan Swing and Beach Break

After our underwater adventure, we cruised to another idyllic location – Little Bay Beach. Here’s where the fun really kicked in! We took turns swinging from the legendary “Tarzan Swing,” a heart-pounding (and exhilarating!) experience that had us shrieking with laughter. Afterward, we relaxed on the pristine white sand beach, soaking up the sun and cooling off in the crystal-clear water. The crew kept the drinks flowing (courtesy of the open bar!), and we were treated to a delicious lunch spread prepared fresh onboard.

What’s Included

  • Paddle board
  • Kayak
  • Lunch
  • Unlimited drinks (open bar)
  • Use of Snorkeling equipment
  • Private tour
  • Tarzan Swing!
  • Gratuities (not included)
  • Hotel pickup and drop-off (not included)

What To Expect

1. Mullet Bay

Here you may use the paddle board and/or kayak. Chillax with a noodle, swim to the beach….we will serve lunch on board.

  • 1 hour 30 minutes
  • Admission Ticket Free

2. Little Bay Beach

In Little Bay we swing from the All Ages Tarzan Swing! We may stop in Baie Longue, Little Bay, Mullet Bay, Simpson Bay, Maho Bay to see the planes.

  • 1 hour
  • Admission Ticket Free

Maho Beach (Pass By)

Pass the airport twice to see the planes take off and land.

Additional Info

  • Confirmation will be received at time of booking
  • Children must be accompanied by an adult
  • Vegetarian option is available, please advise at time of booking if required
  • Not wheelchair accessible
  • Stroller accessible
  • Service animals allowed
  • Most travelers can participate
  • This is a private tour/activity. Only your group will participate
  • Operated by Random Wind Charters

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund. For a full refund, you must cancel at least 24 hours before the experience’s start time. If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded. Any changes made less than 24 hours before the experience’s start time will not be accepted. Cut-off times are based on the experience’s local time. This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

Tailored to Perfection: Your Ideal St. Maarten Experience

Throughout the day, the crew was attentive and ensured our every need was met. They offered fascinating insights into St. Maarten’s history and culture, adding another layer of richness to the experience. We even had the opportunity to choose our itinerary – the crew suggested some amazing spots, but we were ultimately in control. This level of personalization truly made the trip feel special.

The flexibility of a private sailboat charter means you can craft your perfect day. Whether you want to explore more secluded coves, visit popular beaches, or simply sail and relax, the choice is yours. The crew’s local knowledge and willingness to accommodate our preferences made all the difference, turning a great day into an unforgettable one.

More Than Just a Sail: Unforgettable Memories

As the sun began to dip towards the horizon, casting a warm glow on the water, a sense of contentment washed over us. We had spent a perfect day exploring hidden coves, snorkeling in a vibrant underwater world, and creating memories that will forever be etched in our minds. The private sailboat charter was more than just a boat trip – it was an experience that embodied the essence of a Caribbean paradise.

Watching the sunset from the deck of the catamaran was the perfect end to a perfect day. The sky transformed into a canvas of oranges, pinks, and purples, reflecting off the calm sea. It was a moment of pure serenity, a reminder of the beauty and tranquility that a place like St. Maarten can offer.

Why Choose a Private Sailboat Charter?

If you’re looking for a unique and unforgettable way to experience St. Maarten, a private sailboat charter is the answer. Here are just a few reasons why:

  • Unparalleled Intimacy: Escape the crowds and create a personalized experience tailored to your group.
  • Flexibility: Craft your own itinerary, choose your stops, and sail at your own pace.
  • Luxury at Sea: Enjoy spacious decks, comfortable seating areas, and top-notch service from a professional crew.
  • Unwind and Recharge: Disconnect from the hustle and bustle and reconnect with nature and your loved ones.

A private sailboat charter offers a level of exclusivity and luxury that group tours simply can’t match. It’s a chance to see St. Maarten from a different perspective, to explore its hidden gems and beautiful coastline in a way that’s tailored to your preferences.

Ready to Set Sail on Your St. Maarten Adventure?

Whether you’re a family seeking a fun-filled adventure or a group of friends yearning for relaxation, a private sailboat charter is the perfect way to experience the magic of St. Maarten.

So, what are you waiting for? Book your private sailboat charter today and get ready to create memories that will last a lifetime!

From the thrill of the Tarzan Swing to the serene beauty of snorkeling in secluded coves, a day on a private sailboat in St. Maarten is an experience like no other. Don’t miss out on the opportunity to discover paradise in your own way, on your own terms.


  • Karin K

    Meet Karin, the passionate author and founder of StMaartenAdventure.com. My love affair with St. Maarten began in 1994 during a memorable trip. The island's allure was so captivating that I decided to make it my permanent home. Since then, I've been committed to sharing the beauty and wonders of St. Maarten through my adventures and insights. Join me on this incredible journey!

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