Lower Prices than Cruise Lines. Higher Quality, Smaller Tours. Money Back Guarantee. 24/7 Traveler Hotline. 19,780+ Customer Reviews. Guaranteed Return to Ship.19,780+ Customer Reviews

Private Sailing Charter

From $160.00/person to $3750.00/person (Select "Individuals" below) Price varies based on number of individuals in your group
This vessel accommodates groups of up to 37 guests maximum. Please take this information into consideration when booking.
Choose Your Options View My Cruise Itinerary
Tour Departure Date:
Tour Departure Time:
Number of Individuals*:
Tour Details
Tour Details

St. Maarten Private Sailing Charter Day Tour

"All I ask is a tall ship," said the poet John Masefield. You'll realize how he felt as your private sailing charter takes you on adventure after adventure on this St. Maarten excursion.

Climb aboard your sailboat where you will find plenty of space in the shade or sun, on a boat that accommodates up to 37 guests, plus crew on board. Sit back, lie down, hang on and, of course, relax, as the crew welcomes you on board, and the captain prepares to sail.

Join us on this St. Maarten excursion as we sail, swim, snorkel, eat, drink, fish, and swing into the Caribbean Blue for a wonderful day in paradise. Our adventure begins as we set sail for the beautiful, calm French side of St. Martin aboard our 52-foot luxury catamaran for a day of coastal sightseeing, snorkeling, and enjoying life on the water with family and friends.

During your tour of St. Maarten your captain and hostess will take you to quiet bays away from the crowds, where there are all sorts of underwater activities. Don snorkel gear or a float to discover coral, fish, turtles, and maybe even dolphins. You can even try using a paddleboard or an ocean kayak.

If you're feeling adventurous, you can also take a turn on our Tarzan swing as you fly over and into the ocean! This is good, clean fun in paradise for all ages. Bask in the sun on board or stay cool in the shade, your choice. Snacks, as well as a delicious lunch of Caribbean chicken, green salad, french bread, and rice, plus top shelf open bar, make this a memorable day for the whole family!

This private charter is really quite special and perfect for weddings, birthdays, anniversaries, family reunions, etc. Not only will you have the yacht to yourselves, you can discuss the itinerary / destination as well as additional food choices with the operator, who will try to honor any wishes, however, the final itinerary is at the captain's discretion on the day of the tour based on sea and weather conditions and the safety and comfort of the guests.

Shore Excursion Size
Shore Excursion Type
Scenic, cultural, water/beach
Shore Excursion Duration
5 Hours
Activity Level
Shore Excursion Leaves From
Just outside the cruise pier. A taxi (not included, approximately $5 each way) may be preferable, depending on where you are docked. Full details will be provided in your electronic ticket upon confirmation.
Food/Beverage Provided
A delicious lunch of Caribbean chicken, green salad, french bread, and rice, plus snacks and a top shelf open bar is included.
Recommended Dress
We recommend wearing a bathing suit under comfortable clothing and sensible walking shoes. Shoes must be removed while on the boat. A beach towel, sun glasses and sun screen are also suggested.
Guests must be able to pull themselves from the water using the ship's ladder.
5 Stars5Based On 2 Reviews Review This Tour
5 StarsWhat a day!August 06, 2018

Reviewer: Victo J. Sorondo
On July 26, 2018 a group of 19 members of our immediate family traveling in the Oasis of the Seas spent the day aboard the Random Wind on a private adventure that came to be the highlight of our cruise. The catamaran is a splendid vessel with room for all, equipped with all the toys needed to have fun for everyone from the young ones (5 yrs. old) to the elders (73 yrs. old). As nice as the equipment is, the thing that made this a truly memorable day was the outstanding attention to detail displayed by our hosts: Ana, Kristen and Stefan. We were truly blessed to have spent such a wonderful day and thank our hosts for their hospitality.

5 Stars;The highlight of our trip!January 15, 2011

Reviewer: Betsy
This was by the far the highlight of our trip. We had a group of 21 family members and friends of all ages and everyone agrees that it's the best day ever. Diane and her crew were fun, accomodating, laid back, and just super. There's nothing negative that I can say about this. We plan to go back and do it all over again!

View All Customer Reviews