The Best Catamaran Day Sail in St Maarten
Overview
Available languages
5 hours
Mobile ticket
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.
Additional Info
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 VIATOR 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
In case you didn’t get that, we determine the meeting place and will let you know via email. Please check your email including junk mail for the meeting instructions. Thank you. Diane.
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
What To Expect
Mullet Bay
We usually stop twice during the day both; stops are in the Caribbean Sea. We don’t go into the Atlantic Ocean. At the first we snorkel, paddle board, kayak, swim to the beach, hang with noodles.....and have lunch. We shop each morning. Marinated chicken skewers, captain grilled, green salad, baguette, lovely Caribbean rice. Would you like a rum punch with that? At the second stop we swing from the Tarzan swing. Those between 2 and 89 have enjoyed this easy, safe and super fun trapeze-type swing. The bar is always open and included and if you are hungry after swinging - or laughing - have a snack!
Little Bay
This could be the first stop or it could be the second stop depending on the day and the conditions of the sea.
What‘s Included
Unlimited drinks (top shelf open bar)
Snacks
Lunch
Tarzan Swing
Use of snorkel equipment and life jackets
Stand-up paddle board
Gratuities
Options
The Best Catamaran Day Sail in St Maarten
Reviews
1,677 reviews
Total reviews and rating from Viator & Tripadvisor
Very fun! Stopped at 2...
Amy S,Apr 2, 2026
- Review from Viator
5.00Very fun! Stopped at 2 places to swim, snorkel and use the Tarzan swing! Maybe 25 people on board. Food was terrific and unlimited drinks
Absolutely wonderful
A7656DEsusang,Apr 1, 2026
- Review from Tripadvisor
5.00The 5 hour sail was absolutely wonderful. The owner/guide, Anna, was delightful. We went snorkeling, did the Tarzan Swing and had a great time. Lunch and drinks were included. The lunch was delicious. The price was very reasonable.We fully recommend this experience!
RANDOM WIND - Great Vibe, great value
suetD9499CV,Mar 31, 2026
- Review from Tripadvisor
5.00SPECTACULAR ! Anne and Scotty and Mia did everything they could to make this a great day. We have sailed on Random wind several times, dating back to when it was a wooden monohull . I am happy to say , the Vibe has not changed. They keep the group small, the fun high and the boat spotless !
The Best Day: Worth repeating over and over again
Lori O,Mar 30, 2026
- Review from Viator
5.00I would give this activity six stars if I could! Anna, Captain Scotty and Maya treated us like royalty. They served us cold beers, rum punch, pop and water. We ate a delicious grilled chicken and rice lunch. When we stopped to float and snorkel in the ocean, they tossed beers for us to drink while we lounged on our noodles. It was a great experience. One of our friends has done this about seven times if that tells you anything. It’s the only thing he and his wife do when they go to St. Lucia on a cruise. I would do this again as well.
Beautiful day
Sunrise83,Mar 28, 2026
- Review from Tripadvisor
5.00Brilliant 5 hours onboard Random Wind. We were warmly welcomed by Anna (and 🐕Queenie). Mya was a lovely crew member, friendly and always topping us up with drinks. Our first stop was in Simpson Bay where we spent an hour enjoying time swimming. Lunch was fresh and tasty. From there, we went on to Little Bay where guests had the opportunity to use the Tarzan swing (lots of fun) and go snorkelling (equipment provided if needed). We were back in Philipsburg about 15:00. The catamaran was clean, facilities were good. Thanks to captain Scott, Anna and Mya for a fun day.
boat ride snorkeling and Tarzan jump
424alexandriap,Mar 26, 2026
- Review from Tripadvisor
5.00the trip was amazing Saint Maarten is so beautiful the food was fire shoutout Annie and big cap love yall downnn
An absolute MUST when visiting the island!!
350brynnw,Mar 24, 2026
- Review from Tripadvisor
5.00Throughout the years, I’ve take numerous boating day trips in various countries, always having a great experience and enjoying myself. To my immense surprise, the charter I took today was absolutely the best time i’ve ever had. (I’m not even one to write reviews it was just that great!!) The food we were served was DELICIOUS and filling, each stop along the way felt perfectly timed, and the staff were amazing to be around. We ended up being apart of a group around 20 (including my group of 9), and everyone from the young children to older adults had so much fun. HIGHLY recommend and would do it again and again if I didn't have to go back to the U.S in a couple days!! (Shoutout to Queenie: the most nonchalant and cutest boat pup on the planet.)
Best sailing trip out there
Dream37857145484,Mar 22, 2026
- Review from Tripadvisor
5.00We had a great time, the crew was very attentive and fun
Do not pass up on this excursion!
886elainab,Mar 22, 2026
- Review from Tripadvisor
5.00Best boat excursion I’ve been on and I’ve been on quite a few! A lot of boat excursions make you feel like you are just a passenger. This team made you feel like you were right at home. The staff was absolutely terrific. Want to thank Captain Scotty, Anna and Olga for their exceptional hospitality. And cannot forget Queenie! Queenie was such an adorable crew member. She knew every piece of the operation and all the stops. The food was surprisingly terrific. Captain Scotty was barbecuing on deck and the drinks were a’plenty. Could not have had a better time. I highly recommend to anyone - young and old. You will thoroughly enjoy yourself.
Fantastic catamaran sail
605herbh,Mar 20, 2026
- Review from Tripadvisor
5.00Fantastic day sailing snorkeling and swinging on Tarzan swing Scottie and Anna do an amazing job are super friendly laid back hosts!!
From US$145.00
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Operated by Random Wind Charters