Private Tour
Private Sailboat Charter in St Maarten
Overview
Available languages
Mobile ticket
Spend the day out on the beautiful Caribbean Sea on this private sailing charter in St Maarten! Whether your group is two or 30 - you will be comfortable and well cared for - the yacht is yours for the day. With pick up in Philipsburg or Simpson Bay, the choice is yours, just let us know.
Your day includes real sailing on a newly refitted 52 foot catamaran with homemade lunch and unlimited drinks from a top shelf open bar. If you are celebrating, please let us know if you want a cake from the French bakery at no extra cost. Relax on a cushioned seat in the sun or shade aboard the ‘Random Wind’ as you travel up the coast. This family-friendly yacht takes you away from it all; offering beach time, snorkeling, paddle boarding and plenty of fun on board with the Tarzan swing! Enjoy personal attention from our certified and experienced crew.
Additional Info
Infants and small children can ride in a pram or stroller
Service animals allowed
Suitable for all physical fitness levels
Children must be accompanied by an adult
Vegetarian option is available, please advise at time of booking if required
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
What To Expect
Mullet Bay
Here you may use the paddle board and/or kayak. Chillax with a noodle, swim to the beach....we will serve like ch on board.
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
What‘s Included
Private tour
Unlimited drinks (open bar)
Kayak
Lunch
Use of Snorkelling equipment
Paddle board
Tarzan Swing!
Gratuities
Hotel pickup and drop-off
Options
Private Charter Group of 15pax
Book this option for a private charter with your group of 15 people maximum.
Private Charter: Group of 8pax
Private Charter Group of 12pax
Book this option for a private charter with your group of 12 people maximum.
Private Charter Group of 10pax
Book this option for a private charter with your group of 10 people maximum.
Private Charter Group of 11pax
Book this option for a private charter with your group of 11 people maximum.
Private Charter Group of 13pax
Book this option for a private charter with your group of 13 people maximum.
Private Charter: Group of 9pax
Book this option for a private charter with your group of 9 people maximum.
Private Charter Group of 14pax
Book this option for a private charter with your group of 14 people maximum.
Reviews
57 reviews
Total reviews and rating from Viator & Tripadvisor
Best Shore Excursion in 10 years of Cruising!
JoBesana,,Dec 27, 2025
- Review from Tripadvisor
5.00We took this tour as part of a Celebrity Cruises shore excursion and in 10 years of cruising, this was one of the best excursions we have ever done! The boat is lovely, the crew are fun, relaxed and friendly, and the tour itself was amazing! We went to 2 locations to swim and snorkel, with lunch served to us in between the two, which was bbq’d for us right on the boat! The second location had us snorkling over a sunken submarine and a crashed helicopter! The trapeze bar for swinging off the boat was a real treat and so much fun. Captain Scotty, Anna, Jackie, and Amy were great hosts and tour guides and we had a perfect day. When trying to tease out what made this one better than other similar tours we’ve had in the past, there were some little details (all equipment in excellent working order including fins and masks that didn’t fog up, and they didn’t push for tips like some places do (we tipped them more for this alone!)) but really, the crew made us feel like we were sailing with friends. Would 100% recommend!
Random Wind Catamaran
499staceyv,,Aug 13, 2025
- Review from Tripadvisor
5.00Amazing experience with Random wind catamaran with our family of 4. The most fun excursion during our entire trip!! The staff, Anna, anna and the captain were so welcoming, friendly and made sure we were safe and comfortable. The Tarzan swing was awesome for our teenagers and my husband and I. We saw so many fish!!! The owner, Anna was amazing in every way! Highly recommend this excursion!!! Smaller group, lots of drinks, great food-so much to love about this!!!
What a way to spend a day!
Travel455375,,Apr 26, 2025
- Review from Tripadvisor
5.00What a fabulous day trip on a beautiful catamaran. The best part was the gracious hosts. There were just 2 of them and the worked hard to keep everyone happy. They were such lovely, tentative people.
The most amazing day in St Maarten!
Meander02028381859,,Apr 23, 2024
- Review from Tripadvisor
5.00We booked a Private Charter in January 2024 whilst we were in St Maarten for the day on a cruise and we are SO glad that we did! On arrival we were greeted by the very lovely Anna who's boat it is, Jackie who is just wonderful and our skipper for the day. They really went out of there way to look after the whole family! Jackie was always there to make sure that we had a drink in our hand (she makes the BEST rum punch!!) and that we had everything that we needed. Anna was such a great host and the boat was perfect! She encouraged the whole family to join in with the activities such as swimming off the boat, snorkelling and the Tarzan Swing which are things some of us thought we would never do! The BBQ lunch was lovely, and they really went out of their way to help us celebrate a family birthday with birthday cakes from a bakery on the Island (which were amazing!!), music and lots of fun. If you are wondering if to book, just go for it! You won't regret it. This day will always be a special memory for the whole family and we are so glad we choose Random Wind as the whole team were so amazing!!! Thank you so much, and we look forward to seeing you when we are next in St Maarten!
Would Gladly Go Out Again
NCTravelFam,,Apr 14, 2024
- Review from Tripadvisor
5.00We thoroughly enjoyed this catamaran ride with lunch. Captain Scottie, Anna, and Jackie were all friendly, and experienced in handling the catamaran and the guests. Having been to St. Maarten before, the snorkeling sights are only mildly interesting to us, it was the atmosphere on the sailboat, the vibe, that made the day. The curried chicken lunch was good, we both enjoyed taking a turn on the swing and watching the other passengers go out and over. The boat ride itself was a delight, the captain making use of the chop to liven-up the afternoon. The whole excursion felt comfortable, safe, and at ease. These folks provide a superior outing, and yes we touched on nirvana
Wonderful day trip on Red Barron
lisapC8318CJ,,Apr 4, 2024
- Review from Tripadvisor
5.00Captain Mike and Elmira provide an unbelievable experience!!! Plenty of fresh food, drinks, island education, conversation and fun. It was like sailing with friends.
Must do in St Marteen
T1540NPrachelr,,Mar 8, 2024
- Review from Tripadvisor
5.00I cannot say enough great things about Random Wind Charters! We have been on this excursion over three times because we love it so much. The catamaran is in great condition. The crew is phenomenal! They keep the drinks flowing all day. Lunch is delicious. (Both drinks and lunch included) They take you swimming, snorkeling, paddle boards and even the Tarzan swing. Great for all ages! We just got back with our 1.5 year old.
Amazing Day on the water with Random Wind Charters!
S3839RDkathrynb,,Apr 20, 2023
- Review from Tripadvisor
5.00We had a group of 19 people with kids ranging in age from 7 to 15. Our day spent on the waters of St. Maarten was the best day of our 7 night Caribbean cruise! Arranging this private charger with Diane was simple - she was able to provide comprehensive information and took a small deposit via Venmo. Getting from the cruise port to the marina was a short ~10 minute walk (sidewalk). Once there, Anna got everyone ready to board and quickly went through a safety briefing. Then it was rum punches (or juice/soda) for everyone! The service was impeccable! It was a windy day so they were able to adjust a bit to take us to two areas - the first was for swimming, a beach, or jumping from the boat's jump platform (a huge hit!), followed by a delicious freshly prepared lunch
Great day on the water
Gipi2014,,Apr 10, 2023
- Review from Tripadvisor
5.00An excellent day on the Random Wind. Anna and Scottie are amazing and I really enjoyed my day with them on the water. Everything was just perfect. Thanks a lot! Highly recommend this private charter!
Everything the day was promised to be and more!
J6142JUjamesg,,Feb 13, 2023
- Review from Tripadvisor
5.00Anna, Captain Scotty and Jackie were as accommodating as they could be. The beer, rum punch and delicious lunch were plentiful and the atmosphere was so relaxing. We snorkeled, swam and used the trapeze to jump off the side of the beautiful boat. The dog, Queenie, was the star of the day. I highly recommend this tour.
Related Experiences
Operated by Random Wind Charters