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Philipsburg · St Martin St Maarten · St Martin St Maarten

Random Wind Catamaran Sail

Starting From From $157.82 per person Current Project Expedition rate
5 Hours 4.29 / 5 16 reviews Easy activity level Single Day Group Tour Operated by Random Wind Charters
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The Experience

What your day looks like

Sail in the Caribbean paradise of St Maarten on a casual yet upscale catamaran cruise within walking distance from the cruise ships! Your day includes real sailing, homemade lunch, and unlimited drinks from a top shelf 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 sailing 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 on this small-group tour, limited to 30 people. Larger groups can take a private charter.

At a Glance

The experience, in brief

  • Spend the day sailing around beautiful St Maarten
  • See starfish, jacks, moray eel, stingrays, and barracuda whilst snorkeling
  • Winner of numerous awards for service excellence and customer satisfaction
  • Try the tarzan swing, paddle boarding, and snorkeling
  • Enjoy a freshly prepared lunch and drinks
  • Great for cruise passengers and hotel guests alike!
Your Itinerary

Your day, step by step

Day 1

Philipsburg

Boating.

Continued

Philipsburg

Leisure.

Continued

Philipsburg

Paddle Boarding.

Continued

Philipsburg

Snorkeling.

Before You Go

What to know before booking

Included

Snorkeling Equipment Stand Up Paddle Board

Not Included

Gratuities Pickup

Meeting & Pickup

If you are a CRUISE guest: Turn left as you exit the cruise terminal. The walk from the cruise terminal exit will take approximately 8 to 12 minutes. We meet at 9:45 on the dock at Bobby's Marina, Philipsburg If ALL guests on any day are staying on the ISLAND - not cruise ship - then the directions are: Meet on the dock at Nowhere Special next to the St. Maarten Yacht Club in Simpson Bay 9:45.

Planning Notes

Hotel pickup offered: No Confirmation: Manual By Business

Traveler Impressions

What travelers are saying

2025-04-06 5.00 / 5

Great fun crew and pleasant vessel.

2024-12-30 5.00 / 5

Client said it was the best boat day they've been on!

2024-05-28 5.00 / 5

Ms Anna and Captain Scott were the best! Very kind, fun, hospitable & the lunch was amazing!! I would def go out on the water with them again ????

2024-03-19 5.00 / 5

Loved our experience on Random Wind. Having a max of 30 ppl made it so that we had enough space to spread out. The owner was very friendly and made sure everyone had a great time. The Tarzan swing was so much fun. We were able to try paddle boarding for the first time. We had a delicious lunch and plenty of rum punch. I highly recommend this for all ages!

2024-01-31 4.00 / 5

Anna and the crew were outstanding hosts and teammates connecting with each guest like long-time friends. Great time!

2024-01-19 5.00 / 5

We had an amazing day out with Random Wind. The crew was super friendly and kept thd drinks flowing. Stops were great and food was amazing. Highly recommend!

2023-12-29 5.00 / 5

Maybe the best for last! Anna and her crew were great and took care of us all day. Swimming, snorkeling , and the swing were great fun. Drinks were plentiful and lunch was great. Thx!!

2023-11-20 5.00 / 5

We enjoyed our day on the Catamaran. The lunch was nice and the drinks flowed! The owner, skipper and deckhand/bartender (Mel) were all wonderful! We would do this again!

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