Our Feature Attraction: A Day in Paradise!

Please note – most of our trips now leave from Simpson Bay – St. Maarten Yacht Club, 9:45.

The PARADISE DAY SAIL is a day cruise on our luxury sailing catamaran, RANDOM WIND, along the coast of beautiful St. Maarten.

All drinks, food and equipment is included in the cruise rate, so that you have a magical day on the blue Caribbean sea. During this day we sail, swim, snorkel, eat, drink and swing from the Tarzan swing. We also have a stand up paddle board that is really fun to try as well as an ocean kayak.

We go where the Random Wind takes us, dependent on the sea conditions. The Captain makes the call each day about the safest, most comfortable itinerary. Please respect that.

One last thing to remember on your Paradise Day Sail… if you are celebrating something, please let me know – I always find ways to make it special!



The Paradise Day Sail runs from 10AM to 3PM.

We meet at 9:45AM at The St. Maarten Yacht Club in Simpson Bay. 


It is US-$119 per person; US-$95 per child between 5-12 years of age. Kids 4 and under are always free.


We want all of our guests to be comfortable so we try to keep our total to about 32. Everyone has a cushioned seat.


From Philipsburg, we board right from the dock. From Simpson Bay, get out to the boat by 14FT dinghy taking 8 guests at a time. Each trip takes 5 mins or so. Once on the boat we check in. During Covid, most trips leave from Simpson Bay. 


We take Visa, Mastercard, American Express, Paypal or Cash.

Once checked in, we do a quick safety talk and off we go.

Typically motor out of the bay and if there is enough wind, we shut the engine off and make way completely under sail when we can.

While underway we serve drinks, with and without alcohol.  We do carry top shelf so if you have a favorite – be sure to ask. Also, have sodas, juices and bottled water.

The beaches are lovely and quiet. Snorkeling you may see starfish, jacks, moray eel, stingray, barracuda, blue tang among others. Turtles also may show up.

Some choose to stay on board and chill on the cushioned seats. Some in the sun, some in the shade.

At the first stop, try out the stand up paddle board, kayak around for a bit; chill in the Caribbean Blue with a noodle and a drink.

At the second stop, our attention is on the tarzan swing and guests around the boat.

After about an hour – lunch is ready. Homemade in the yacht’s galley and on the grill – fresh every day.

A delicious blend of mild spices and coconut milk make this chicken and rice dish a favorite. Cookies and chocolates follow.

If you would like to suggest a dedication – please talk with your hostess beforehand.

Call for last dip before we head over to another bay. This is a cool place with deeper lovely water; perfect for the infamous Tarzan Swing. Have a go, it’s super fun!

Everyone can do it – we stand on the rail and hold on to a solid trapeze swing, and in we go! You can do this alone or with someone.

Your crew can show you the back flip and front dive; but simply holding on and swinging in is such good fun.

On the way back nice snacks are served. Of course drinks and music are served all day until you are off the boat – and even then, you are welcome to take a roadie!

While relaxing on the way back, we will let you know that we have shirts available – There is also an opportunity if you wish to leave a gratuity.

Back on the dock about 3:00.

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