St Maarten Catamaran Cruise: Unforgettable 5-Hr Island Escape
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Sail in the Caribbean paradise of St Maarten on a casual yet upscale cruise within walking distance from the cruise ships and close to most resorts. Some days we leave from Philipsburg and other days we leave from Simpson Bay. Your day includes real sailing, homemade lunch and unlimited drinks from the open bar. 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; snorkeling, paddle boarding and plenty of fun on board with the TARZAN SWING! Enjoy personal attention on this small-group tour, limited to 30 people.
Reviews
Reviews and Rating (Tripadvisor)
5 stars
Reviews by Tripadvisor travelers
807RachaelS, 11/4/2025 6:27:22 AM
We had an amazing day with Random Wind. Anna & Jackie were so helpful and friendly. The day we were in port was windy and they offered us a change of date or a refund if we didn’t want to sail due to rough seas. We decided to go ahead and we were so glad we did. Our kids loved the day and were so well looked after. They especially enjoyed the swing and jumping off the boat. My daughter loved Queenie the dog! The catamaran was lovely and the food and drink were fantastic. St Maarten is beautiful and we would definitely do the trip again if we are ever back in St Maarten.
H683JBbenb, 11/3/2025 8:50:12 AM
Random Wind certainly lived up to expectations from 15 years ago. Now, a beautiful catamaran with a new crew who were exceptional in their hospitality. We had a fabulous day sailing, snorkeling, eating and drinking continuously. Thank you Scot, Anna and Jackie for looking after us so well and creating the fun
T5387UTloril, 10/23/2025 3:23:46 PM
Fun, exciting, and relaxing all in one. Once you step aboard you have no worries for the coming hours. The amazing staff take care of everything. Swim, snorkel, swing…or laze around on a beautiful boat. Delicious lunch and the crew truly made it an exceptional day!
Karrie S, 10/19/2025 7:06:51 PM
This is the best catamaran trip in St. Maartens! Fantastic day with delicious food, snorkeling and drinks. Gracious hosts and amazing views made this trip the top of the week. We will definitely return and highly recommend it.
Nicki M, 10/9/2025 11:47:07 AM
This is hands down the best catamaran sail tour I’ve ever done. I went back for a second time and had just as good a time. Great for families, friends, couples. The crew is so friendly and takes care of everyone. The Tarzan swing is a definite highlight!
Nomad09400787212, 10/9/2025 10:32:45 AM
Our hosts Meghan, Anna and Scott were amazing! Views were stunning! Lunch was delicious and our afternoon flew by. We went snorkling,swimming and jumping from a fun rope swing. There was something for everyone.
GoPlaces60193879601, 10/6/2025 11:00:52 AM
We had the most amazing experience. Captain Ana was very attentive and made sure we were all enjoying ourselves while making sure we were all safe. Captain Scott was amazing as well and we cant forget to mention the boss queenie. The waters were beautiful. Lunch was refreshing and sooo yummy. The swing was sooo much fun. Our group was very friendly and even though a quick shower came thru we made the best of it and had a time of our lives to remember. As for pre-boarding Diane was very communicative and that help alot. Thank you again for an amazing day on water and new friends that we made. I cant wait to come back to the island and do this all over again.
210kirstenz, 10/5/2025 10:11:51 AM
This exceeded our expectations! Not only was the experience itself wonderful, but the food and drinks were absolutely divine. I wish I had time to go again!!
Jose P, 10/1/2025 9:18:08 AM
It was one the best excursion I ever went on, capitán Scotty, Ana, & Megan were the best, and of course the doggy queen, the trip was perfect, drinks kept on coming, and food was delicious, it's the perfect 5 hour getaway for the day. I know when we come back we will book it again.
Cmarleaux, 9/30/2025 4:59:40 PM
We met the owner of Random Wind thru a mutual friend and decided to give it a try. I have to say, it was a really fun experience. The boat is beautiful and the crew is very fun. The trip was beautiful….went to Little Bay for snorkeling and lunch then sail to Mullet Bay for more water time and the infamous Tarzan Swing…..it was a great day and I highly recommend it to anyone in St. Maarten.
- Service animals allowed
 - Public transportation options are available nearby
 - Suitable for all physical fitness levels
 - Minimum age to consume alcohol is 18 years.
 - Within walking distance of your ship.
 - Parking available
 - Travelife Sustainability Partner
 - IMPORTANT! PLEASE IGNORE WHAT THE TICKET SAYS REGARDING MEETING PLACE AND WATCH FOR THE EMAIL FROM DIANE - ALSO CHECK JUNK MAIL. We determine the meeting point and will send it to you the week before via the email you give. You must check your email NO MATTER WHAT THE TICKET SAYS - The meeting place will be emailed
 
Departure point
PLEASE IGNORE THE TICKET AND GO TO WHERE YOU HAVE BEEN INSTRUCTED VIA EMAIL FROM DIANE. We have 2 meeting points - we will determine the meeting point and email you the meeting instructions to the email you give when you book. Please tell us if you are on a cruise ship or staying on the island.Return details
Sail in the Caribbean paradise of St Maarten on a casual yet upscale cruise within walking distance from the cruise ships and close to most resorts. Some days we leave from Philipsburg and other days we leave from Simpson Bay. Your day includes real sailing, homemade lunch and unlimited drinks from the open bar. 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; snorkeling, paddle boarding and plenty of fun on board with the TARZAN SWING! Enjoy personal attention on this small-group tour, limited to 30 people.Redemption
Do your sustainability part: do not print this ticket. Our reservation system is digital - we have your info - all you need is your name and a smile. If you have this on your phone - that works but please don’t print. ☺️ We have two meeting points on the island. We can never be at both places at once. WE WILL CHOOSE THE MEETING POINT according to information we receive from all guests; that is why we ask if you are staying on the island or coming in on a cruise ship. If you have not already done so, please let us know. We will determine the best meeting point for the day of your tour and let you know. We use email most to communicate. Please check your email - the one you gave when you booked - Please check your SPAM/JUNK folders too. You can always reach Diane at info@randomwind.com or 757-660-5624 phone/text/WhatsApp. *Please note: St Maarten does not participate in Daylight Savings. This means from Fall through Spring the time is one hour ahead of Eastern Standard Time (EST) and most ship times. Please watch your email for meeting instructions. If you have ANY questions or concerns, please call and /or email 757-660-5624 / info@randomwind.com24 hours before travel date - 100% refund
Less than 24 hours before travel date - 0% refund











