RANDOM WIND CHARTERS

The Spirit Of St. Maarten

Reviews from millions of Tripadvisor travellers place this in the top 1% of things to do worldwide.

St. Maarten Sailing Charters


Looking for a group-friendly, family-fun, adventure out on the beautiful waters? Join us at Random Wind Charters! With each adventure, we sail, swim, snorkel, eat, drink and swing into the Caribbean blue on the original Tarzan swing! 


When you’re aboard our vessel, it’s more than just a normal sailing tour. You are our guest, and our crew strives to provide you with the best experience possible! With our charters, a delicious lunch is cooked on board, there is a full & open bar, and all gear (snorkel gear, life jackets, noodles) included. The full-time crew is internationally qualified & their experience is clearly demonstrated; guests feel safe, comfortable & cared for. 


We are COVID-19 Safe!

We're here to make sure that your excursions are enjoyable, memorable, AND safe!

Our Sailing Charters

Choose any of our sailing charters for a memorable experience!

Perfect for family-fun.


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    PARADISE DAY SAIL

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$129 USD per person

$105 USD/child between 5-12 years old. 4 and under FREE!

Maximum is 30 passengers

Available 10 AM to 3 PM

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    SUNSET CHARTER

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Starts at $500 USD

Up to 8 passengers

$40 for each additional up to 30

Available 5 PM - 7PM (Approximate)

NOT AVAILABLE

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    PRIVATE CHARTER

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Starts at $3300 USD for 8

$3300 for 8 People

$60 for each additional up to 30

Available 10 AM to 3 PM

BOOK NOW LEARN MORE

Our Sailing Charters

Choose any of our sailing charters for the experience of a lifetime!


  • Slide title

    PRIVATE CHARTER

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Starting at $3300 USD for 8

Starts at $3300 for 8 People

$60 for each additional up to 30 People

Available 10 AM to 3 PM

BOOK NOW LEARN MORE
  • Slide title

    PARADISE DAY SAIL

    Button

$129 USD per person

$105 USD/children 5-12 years old. 4 and under FREE!

Max capacity is 30 passengers

Available 10 AM to 3 PM

BOOK NOW LEARN MORE
  • Slide title

    SUNSET CHARTER

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Starts at $500 USD

Up to 8 passengers

$40 for each additional up to 30

Available 5 PM - 7PM

(Approximate)

NOT AVAILABLE

LEARN MORE

Not Your Typical Boat Trip


A day with Random Wind Charters is unique. You’ll experience an excursion different from other boat trips. We offer a blend of fun, comfort, and homestyle hospitality that will leave you with great memories of the Caribbean. 


Our crew is exceptional on all levels. You will be safe and cared for, and our crew will make sure your day is to your full satisfaction. If you’re looking for fun, excitement, relaxation, adventure, or a combination of them all, we’re here to make it happen for you. Nowhere else will you find a personable, highly-qualified, kind, respectful, and hospitable crew.

BOOK YOUR CHARTER
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  • 4 dolphins swimming by catamaran yacht

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25

Years of Sailing in St Maarten

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6679

Trips Taken

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89161

Happy Customers

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  • two women sitting on Random Wind yacht holding drinks

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  • Plate of grilled chicken rice and salad served for Lunch on Random Wind Charters

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OUR MISSION STATEMENT


  • Encourage fun and laughter in a stress-free environment


  • Treat all people equally and with respect


  • Enjoy alcohol responsibly so as to enhance the good time we are having


  • Take pleasure in the waters of Sint Maarten – Saint Martin as a green company; appreciating the beauty and leaving no footprint.
READ MORE ABOUT US

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We Have Award Winning Excursions Since 1999

Check out who we're working with!

See what our customers say about us!

Random Wind Charters Promotes Sustainability!


Random Wind Charters is pleased to announce to have been admitted into the EU-funded SUSTOUR project that supports over 600 small and medium-sized tour operators and travel agents from 35 European countries in improving their sustainability performance.


Sustainability is a core value of the tourism experiences that we want to provide for our customers. Therefore, we are happy to participate in this one-year support programme running from mid 2022 to mid 2023 and we commit to using this opportunity and actively improving our sustainability management and performance.

#SUSTOURproject #SUSTOURforsustainability

#SUSTOURparticipant #promotingsustainability

#aimingforTravelifecertification #SUSTOURacceleratorprogramme 

This Is How We Play the Game

Our Zero Tolerance Stance

Whether you are a Guest or a Crewmate at Random Wind Charters

We Do Not Accept Racism or Discrimination of Any Kind

We Believe

You belong here, and we welcome you as you are.

Your unique qualities are important.

You will be treated with dignity and respect.

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