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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 22 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 with a spa quality mud bath and be pampered by an expert crew
  • Small-group tour limited to 22 ensures a more personalized experience

What You Can Expect

Small-Group Day Sail in St Maarten

Set sail in St Maarten!

Swing into the welcoming waters of the Caribbean on an exciting—and safe—Tarzan trapeze aboard the Random Wind, a 54-foot (16-meter) sailing yacht. This family-friendly boat offers three ‘chill lounges’ where you can relax on cushioned seats with backrests as you listen to your own tunes on the stereo system.

Your captain and hostess will take your small group up the coastline of St Maarten and stop at two beaches for fun in the sun. Visit both the French and Dutch sides of the island, where you can dip into the sea and swim, snorkel, and go stand-up paddle boarding. Give yourself a spa quality bath and enjoy a homemade Caribbean lunch such as coconut chicken with rice—mildly spiced and cooked fresh on board while you play.

Make new friends on this unique St Maarten sailing adventure as you relax in the sun or shade. Sip drinks from the open bar, including complimentary top shelf rum, gin, vodka and tequila as well as beer, juice and bottled water.

Customer Reviews

Larry S

5 star rating: Highly Recommended June 2016

Best day! Tons of fun for all ages. Trapeze swing was Big hit for our teenagers. We will do it again on our next trip!!!

James P

5 star rating: Highly Recommended May 2016

We could not have asked for a better day or better people to spend the day with.

Marianna M

5 star rating: Highly Recommended April 2016

The excursion was great. Very well organized. Lots of fun!

Denise M M

5 star rating: Highly Recommended August 2015

One of my favorite excursions ever!! The boat was amazing along with the staff. Good food and drinks. My kids had the time of their life swinging from the boat and snorkeling. There was a lot do do on this trip from paddle boarding to lounging on a noodle. I would recommend it to anyone. If I ever go back I will definitely book this trip again!

James M

5 star rating: Highly Recommended March 2015

This is the best trip on the island! I sent my son and his fiancee on the same trip in December and they had a blast. Relaxing, fun,
foods great, plenty to imbibe, and the crew is top notch. You can;t go wrong with Diane, Trevor and a day on the random Wind!

Danielle C

5 star rating: Highly Recommended January 2015

We had a great time on this excursion. The crew were interesting and knew what they were doing. The snorkeling wasn't the best but I'm going to assume that's because of the windy conditions and turned up sea. The food and drinks were great and the boat is very relaxing. We had a great group of people and everyone had a blast jumping off the swing. I highly recommend this tour and look forward to using them again when we go back.

Gary G

5 star rating: Highly Recommended September 2014

This was our favorite excursion. Very relaxing yet lots to do and see. The crew was very attentive and personable. Plenty to eat and drink. Great boat! We would definitely take again.


5 star rating: Highly Recommended May 2014

Great trip and day out on the water. Captain was professional and fun, drinks and food were delicious!

steve m

5 star rating: Highly Recommended February 2014

great trip. had a blast. started out with tender to sailboat, then set sail in beautiful waters on great boat with diane, who was such fun and a great hostess. trevor was great capt. husband loved the swing. lunch and snacks great along with anything to drink. would do this again, for sure. thanks for the memories

Kurt T

4 star rating: Recommended June 2015

this was an amazing time on the water...Though the captain was not very personal and sparked an attitude, Rose the owner was very personal and I could tell she really loved to see people smile and enjoy themselves. I would do this trip again and attempt to give the captain a hug :

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