Random Wind Charters
The Spirit of St. Maarten

Do you want to be spoiled?
Do you want a lovely luxury sailing catamaran with cushioned seating in the sun and shade with a crew that is top rated for service as well as safety at sea?

We sail, swim, snorkel, eat, drink and swing into the Caribbean blue on the only and infamous ALL AGES Tarzan Swing.

Delicious lunch cooked on board, full open bar and all gear (Snorkel gear, life jackets, noodles) included.

Full-time crew is internationally qualified & their experience is clearly demonstrated; guests feel safe, comfortable & cared for.

Choose one of these sailing charters for the experience of a lifetime!

Your All day Sailing Excursion

Your Exclusive Sailing Trip

The Green Flash on a Caribbean Horizon

Interested in a fishing charter or small private charter? Ask me about HALF-A-WAKE, a 35 foot power boat.

We have received a previous request. Please Call 757-660-5624 or 721-587-5742 for assistance.


“We’ve been on a lot of nice catamaran cruises but this one was over the top! The lunch, snacks, dessert were delicious and of course we can’t forget the cocktails and beer! We can’t say enough about the crew they were fantastic they ran around waiting on this all day!”
Lynn K, TripAdvisor 08/15/2019

Even a little rain didn't stop this from being an amazing time!

“So much fun. Anna, Luke and Dom did an amazing job the entire trip. Constantly walking around to make sure everyone was happy and had everything they needed (cocktails too). So friendly!  Our trip started with a quick rain storm but that did not slow them down. 2 great stops with paddle boards, kayaks and snorkeling. Last stop was the Tarzan Swing! Definitely a must try! Food was delicious. Our day was perfect. Thanks to you all.”
Deb C, TripAdvisor 08/07/2019

Best Experience!

“They were so fun and energetic! You can really tell how much they love their jobs and the island. They went above and beyond to make sure we felt as comfortable as you can because unfortunately I got very sea sick and Anna did everything she could to make me feel better. We were super impressed with the lunch they served! Favorite part was Captain Luke throwing beers to us while we floated in the water with our noodles! Such an awesome day and would highly recommend!”
Kurt123, TripAdvisor 08/02/2019

Award Winning Excursions Since 1999

2020 TripAdvisor Travelers Choice Award

TripAdvisor’s 2020 Traveler’s Choice Award
TripAdvisor’s Certificate of Excellence Award: 2013, 2014, 2015, 2016, 2017, 2018 and 2019
Luxury Travel Guides The Service Excellence Award 2017 & 2018 and Adventure Activity of the Year 2016
Travel and Hospitality Award’s Sailing Company of the Year 2018

Our 5-Star trips are not just typical boat trips.

It’s a unique boating adventure that you are sure to love and remember for years to come. This St. Maarten activity is perfect for all ages – kids and adults alike.  We make sure that you have the room and everything else you need to have the best day possible while enjoying the crystal clear waters of St. Maarten.

Choose Paradise Day Sail, Private or Private Sunset Charters for the experience of a lifetime!

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