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St Martin / St Maarten
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Private Sailboat Charter in St Maarten

Select Date and Travellers
per group (up to 15)
2 travellers
You’ll have 3 starting options
See Important Information for details
  • 1
    Mullet Bay
    Stop: 90 minutes -
    See details
  • 2
    Little Bay Beach
    Stop: 60 minutes -
    See details
    Pass by Maho Beach
You'll return to the starting point
    Important Information
    Departure Point
    1: 26 Juancho Yrausquin Blvd, Philipsburg, Sint Maarten
    2: Buccaneer Beach Bar, Billy Folly Road, Simpson Bay, Sint Maarten
    3: Skip Jack's, Welfare Rd, Simpson Bay, Sint Maarten
    Departure Time
    9:45 AM
    Return Details
    Returns to original departure point
    • Beverages
    • Paddle board
    • Kayak
    • Lunch
    • Snacks
    • Unlimited drinks (open bar)
    • All activities
    • Use of Snorkelling equipment
    • Private tour
    • Gratuities
    • Hotel pickup and drop-off
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    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 experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund
    • This is a private tour/activity. Only your group will participate
    Cancellation Policy
    For a full refund, cancel at least 24 hours in advance of the start date of the experience.
    Traveller rating
    • 20
    • 0
    • 1
    • 0
    • 0
    Traveller type
    Time of year
    Selected filters
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    • English
    Popular mentions
    We have been enjoying the Random Wind for 5+ years and every year is better than the next! So much fun. We have sailed with kids 3 years old all the way up to family and friends 70 years young! The crew is wonderful, the lunch is great and the drinks are cold and plentiful! Can
    Read more
    Response from Diane S, Owner at Private Sailboat Charter in St Maarten
    Responded 3 weeks ago
    Thanks so much!
    Read more
    If you doing want to be crammed in with tons of other people ..this is the day cruise for you. I had been on their previous sailboat, which evidently is sitting in the bottom of the Lagoon. The day we sailed (1/23/20) started off cloudy and overcast. It went from bad to
    Read more
    Response from Diane S, Owner at Private Sailboat Charter in St Maarten
    Responded 4 weeks ago
    Sorry you only had a 3 star day. Please don’t tell others that they won’t see anything when everyday they do. The life in all the sea is beautiful, and everywhere unless you can’t see it. But this day is about snorkeling and so much more. Most are able to fully enjoy ALL it has to offer.
    Read more
    The Random wind team was one of the best we have experienced! They were professional and went above and beyond to make our day with them wonderful! We had the best time sailing the beautiful Caribbean Sea with them. We can’t wait to do it again. Thanks for the great memories
    Read more
    Response from Diane S, Owner at Private Sailboat Charter in St Maarten
    Responded Nov. 10, 2019
    Thank you!
    Read more
    Anna and her crew are total professionals and work hard to accommodate all guests and ensure that everyone has a great time. We appreciate their hard work to make this a great experience and a memorable one. Thank you!!!
    Read more
    Response from Diane S, Owner at Private Sailboat Charter in St Maarten
    Responded Nov. 10, 2019
    Thanks so much!
    Read more
    My wife and I needed to find an activity that my mother-in would find relaxing. Jet skis and parasailing just weren't on the list. The Random Wind came tot he top when we researched catamaran tours. We weren't disappointed! Anna and Captain Coy were friendly from the start and
    Read more
    Response from Diane S, Owner at Private Sailboat Charter in St Maarten
    Responded Nov. 7, 2019
    Thank you so much!
    Read more
    About the operator
    By: Random Wind
    Alex & Jen
    Truly The Best Catamaran Day Sail in St Maarten!
    This is a must do activity for anyone visiting St. Marteen. 6 years ago my wife and I came to St Marteen and
    Read more
    Winchester, Massachusetts
    Best catamaran tour on the island
    by far the best catamaran tour on the island, hands down. What makes it special first off is the crew, which
    Read more
    St Martin / St Maarten
    Exceptional day sail!
    The team aboard Random Wind gave us an exceptional day out at sea! What an amazing crew who tends to your every
    Read more
    Great fun for the family
    Had a really lovely day with Anna, Koy, Prince and the crew. Was a bit windy so we chilled at Simpson bay, had a
    Read more
    Robin P
    Amazing customer service and honesty!
    We had booked a large group of friends (18) to sail on Random Wind a this past Friday. Although the sun was
    Read more
    Mike A
    Great day
    Was great. Crew was great and always asking if you needed anything. It is a tour you won't be sorry for taking.
    Read more
    Jamie S
    Andalusia, Illinois
    Felt like family!
    We had a blast on this tour! We truly felt like part of the family while we were on board! Great snorkeling, great
    Read more
    Hillary T
    A Great Excursion!
    We spent the day on a lovely catamaran with lovely people. Not only did the crew provide a full bar, soda’s and
    Read more
    St Maarten Day Sail
    This was absolutely the best and most amazing day trip we’ve done. Anna and Coy worked hard to make our day
    Read more
    Gayle M
    Random wind st Maarten
    Had one of the best days ever. Anna and Coy were wonderful and I would recommend this trip to all. Relaxing
    Read more
    Key Details
    • Duration: 5h
    • Mobile Ticket Accepted
    • Instant confirmation
    • Languages Offered: English, Portuguese, Spanish
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    • Free Cancellation up to 24 hours in advance
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