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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.

Highlights

Why travelers choose this experience

  • 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.

Planning Details

Before you go

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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