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Small-Group Day Sail in St Maarten

Philipsburg, Caribbean
Book online or call: (888) 651-9785(888) 651-9785

From US$118.99

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5 hours (Approx.)
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Cruise on the ultramarine waters off St Maarten during this 5-hour yacht excursion from Simpson Bay. Step aboard the family-friendly yacht, the 'Random Wind', to meet your friendly captain and crew as the boat departs the pier. Find a comfortable spot on one of the boat's cushioned seats in the shade or sun and get to know your small group of 32 people or less as you watch the coastline fade into the distance. Journey to both the French and Dutch sides of the island to visit several beaches and relax in the soft sand. Go snorkeling, stand up paddleboarding or try out the Tarzan swing. Eat a homemade lunch and sip drinks from the top shelf bar.
  • 5-hour St Maarten yacht sail aboard the Random Wind
  • Snorkel or try the stand-up paddle board in the Caribbean
  • Trapeze into the water on the famous Tarzan swing aboard the sailboat
  • Cruise along the coastline to beaches on the Dutch and French sides
  • Relax and be pampered by an expert crew
  • Small-group tour limited to 32 ensures a more personalized experience

Traveler Photos


131 Reviews
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Reviews by Viator travelers
Review of Catamaran sail
Alex E
, Aug 2019
Anna and Luke did a fantastic job caring for the passengers. My kids had a great time. Trapeze swing was excellent. They did great job caring for my 80 yo dad. Only complaint was we had 30 people on what was to be a 22 person max trip. Also drinks were not traditional type of drinks. We all had a great time!
Response from Host , Aug 2019
Sorry for the misunderstanding. The boat that sank in Hurricane Irma had a max of 22. The new boat, with the same name, has a max of 37 but we limit it to 32 so you are all comfortable. I am glad you had a great time!
Great Day
, Jul 2019
Anna and Luke provided excellent service. The rum punch was non stop and the snorkeling and trapeze swing were a hit with the family.
Response from Host , Jul 2019
Thank you!
Kaplan Family Sail on Random Wind
, Jun 2019
Our Family of Six had a wonderful time sailing on June 4th on the Random Wind with Captain Luke, Darcy, Anna and Prince as they were so welcoming and kind throughout the entire time on board. The girls loved the open deck space, beautiful stops with time for swim, snorkel, noodles and lots of beer flying from boat to swimmers!!! Lunch service and food was fabulous and just enough for the sail. Some of our family did the Tarzan Swing and it was a highlight and memorable moment during the sail. Captain Luke gave us a chance to see Maho Beach with a Large Commercial Plane fly over us and land at airport too. My granddaughter fell in love with Price and was delighted to learn he was a rescue puppy from the Hurricane last year. The Random Wind is a beautiful boat and very, very comfortable with covered, padded bench for shade and plenty of deck for sunning. We would certainly love to sail again in the future with this fantastic crew!!!
Response from Host , Jun 2019
Thank you so much!
Best excursion ever
, Jun 2019
We were really pleased with this excursion and enjoyed the family hosting the excursion. Highly recommend.
Response from Host , Jun 2019
Thank you!
Best day of our trip!
, May 2019
Where do I begin? From the moment we stepped on to the dock to check-in for our cruise, Anna was upbeat and bright - her energy instantly contagious. After our warm welcome from Anna, we were no sooner greeted by her 4-legged friend, Prince, Anna's hurricane rescue pup. As soon as we began sailing, Anna and Luke hustled to make sure no hand was left drink-less and explained the course for the day. The first stop consisted of paddle boarding, kayaking, swimming, snorkeling, floating in the water while Luke tosses you beers, and jumping off the side of the boat. We wrapped up the first stop with a delicious lunch and set sail for our second stop - where we anchored off a cliff in little bay and swung endlessly from the Tarzan swing. The entire essence of our time on Random Wind was something from a dream - we were relaxed, we were laughing constantly, we were having fun and we made friends. Some how, Anna and Luke were able to create a family-feel between the some 20 of us on board that day. I was sad when we pulled back to the dock at the end of our trip and hugged Anna and told her I'd miss her. and I do! This cruise was most definitely the most wonderful part of our stay on St Maarten. Thank you Anna and Luke!
Great trip!
Michael S
, May 2019
Great catamaran trip! Anna and staff made this a very enjoyable trip. All the rum punch you can drink😎 They were great host and kept everyone safe.
Don't trust Viator for bookings
Rhonda G
, Mar 2019
Was very excited to find this excursion via VIATOR while visiting my daughter in SXM. Everything went through fine, received confirmation and tickets. Then at midnight an email was sent that that day & time was not available and gave two options which were not possible. VIATOR Should not have confirmed booking if space wasn't available. VERY DISAPPOINTED!!
Perfect day on the water!
, Mar 2019
We really enjoyed our day sailing in St Maarten with Luke and Anna. The food and drinks were great! The seas were rough so we were only able to stop in Little Bay. At the stop there was plenty of time to snorkel, paddle board, kayak or just hang out in the water. It was very relaxing with lots of places to lounge and take in the sights.
Wonderful day!
, Dec 2018
What a great day! Fun and friendly crew! Plenty of activities including kayaking, paddle boarding, and snorkeling! Great food and drink!
, Aug 2018
This was the BEST day 5 hour sail with a great crew we had a small group on the boat! They take such great care of you get on the boat and they ask you what you would like to drink and the lunch was fabulous! The entire day was such fun! Thank you Anna for the wonderful service and day!

Product code: 6239SGSAIL

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