Tours and Tickets
Private Sailboat Charter in St Maarten
5
LIKELY TO SELL OUT*

Private Sailboat Charter in St Maarten

By Random Wind
Recommended by 97% of travelers
This number is based on the percentage of all Tripadvisor reviews for this product that have a bubble rating of 4 or higher
from
₱185,150.89
per group (up to 8)
from
₱185,150.89
per group (up to 8)

Lowest price guaranteeReserve now & pay laterFree cancellation

Ages 0-120
Duration: 5–7 hours
Start time: Check availability
Mobile ticket
English


  • Paddle board
  • Kayak
  • Lunch
  • Unlimited drinks (open bar)
  • Use of Snorkelling equipment
  • Private tour
  • Tarzan Swing!
What's not included
  • Gratuities
  • Hotel pickup and drop-off


Departure details
  • 26 Juancho Yrausquin Blvd, Philipsburg, Sint Maarten
  • Nowhere Special, Welfare Rd, Simpson Bay, Sint Maarten, Welfare Rd, Simpson Bay, Sint Maarten
Return details
  • Returns to original departure point

  • Not wheelchair accessible
  • Stroller accessible
  • Service animals allowed
If you have questions about accessibility, we’d be happy to help. Just call the number below and reference the product code: 6239P4

  • Confirmation will be received at time of booking
  • Children must be accompanied by an adult
  • Vegetarian option is available, please advise at time of booking if required
  • Most travelers can participate
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund
  • This is a private tour/activity. Only your group will participate

  • For a full refund, cancel at least 24 hours in advance of the start date of the experience.

What you can expect during your visit
  • Regular temperature checks for staff
  • Regularly sanitized high-traffic areas
  • Temperature checks for tour participants upon arrival
  • Guides required to regularly wash hands
  • Hand sanitizer available to travelers and staff
  • Contactless payment for gratuities and add-ons
  • Gear/equipment sanitized between use
  • Social distancing enforced throughout experience
  • Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.

How much is Private Sailboat Charter in St Maarten?
Private Sailboat Charter in St Maarten price starts from ₱180,574.56. Discover and book Private Sailboat Charter in St Maarten on Tripadvisor
What is the Private Sailboat Charter in St Maarten cancellation policy?
Private Sailboat Charter in St Maarten cancellation policy: For a full refund, cancel at least 24 hours in advance of the start date of the experience. Discover and book Private Sailboat Charter in St Maarten on Tripadvisor
Which company provides Private Sailboat Charter in St Maarten?
Private Sailboat Charter in St Maarten is hosted by Random Wind. Read reviews, discover additonal experiences or contact Random Wind on Tripadvisor. Discover and book Private Sailboat Charter in St Maarten on Tripadvisor
How much time do I need for Private Sailboat Charter in St Maarten?
On average, this experience will take approximately 5h. Discover and book Private Sailboat Charter in St Maarten on Tripadvisor

If you have questions about this tour or need help making your booking, we’d be happy to help. Just call the number below and reference the product code: 6239P4

Itinerary
  • You’ll have 2 starting options
    See departure details
  • 1
    Mullet Bay
    Stop: 90 minutes
    See details
  • 2
    Little Bay Beach
    Stop: 60 minutes
    See details
    Pass by
    Maho Beach
  • You'll return to the starting point
+
About the operator

Don’t take it from us – here’s what people have to say about this operator.

kimberlywH7885TF
kimberlywH7885TF
00
Catamaran Excursion
Such a great experience! Captain Scotty, Anna and Queenie were wonderful hosts. The catamaran was clean and the v
ababaier
ababaier
00
A Perfect Trip!!
My best friend and I were in St. Maarten celebrating our 40th birthdays. We had the best day with Anna and Scotty o
Jennifer M
Jennifer M
00
So much fun! Definitely recommend!
We had an excellent day on the water with the crew of Random Wind. They are attentive and friendly. The served is
Voyage28814955864
Voyage28814955864
00
Amazing day with lots of fun!
We sailed on Random Wind with 1 adult and 2 teens for a snorkel/swim spot and another spot for snorkel/swim/ Tarzan
R1580APjohnp
R1580APjohnp
00
Awesome
This was a great trip and great value. Excellent hosts, good food and drinks. Would go again we even got to sail fo
jubyleerhyannej
jubyleerhyannej
00
Amazing Excursion
Very nice ride and service! Food was good as well I would highly recommend. Coordinator provided info via text and
GAM1970
GAM1970
00
Hand down the BEST!!!
This is the one time that I relied on a review to purchase tickets and so glad that I did! Anna (host extraordinai
donellam2023
donellam2023
00
Ten out of ten, would recommend!
We celebrated my best friend’s birthday on the boat. Anna and Scott were amazing and we had a fun group of people o
williamgregory1
williamgregory1
00
Great and Enjoyable Catamaran Cruise
This was an excellent and enjoyable experience. Anna and Scott were superb and assured a fun time by all. The cat
May A
May A
00
Best experience on St Maarten
For starters they’re very accommodating. My father has brain cancer and has been going through chemo which slows hi
Naffhf
Naffhf
00
Great day in St. Martin!
We had a great day on the Random Wind! The hosts were so hospitable and served a fresh lunch and kept the drinks co
mariamquarium
mariamquarium
00
A good time!
10/10 experience - would recommend! The drinks were flowing, my cousin and I had an amazing time on the boat & we m
228lesr
228lesr
00
Enjoyable but missed out on the airport beach
We had a wonderful day of swimming, snorkeling and even jumping with a Tarzan swing. Wonderful lunch. Just missed o
S5307XAkyler
S5307XAkyler
00
Kyle Robertson
This experience was one of the best excursions I’ve ever taken and well worth the money! Our captain and tour guide
akdabson2022
akdabson2022
00
Incredible Catamaran!
What an incredible day!! Anna, Scotty, and Queenie were amazingly kind, helpful, and so much fun. The drinks and lu
Detailed Reviews: Reviews order informed by descriptiveness of user-identified themes such as cleanliness, atmosphere, general tips and location information.
Popular mentions

5.0
46 reviews
Excellent
45
Very good
0
Average
1
Poor
0
Terrible
0

Nicole F
Zionsville, IN1 contribution
Feb 2022 • Family
Our group of six adults and five teens did a half day private excursion with Anna, Fiona and first mate Queenie. It was by far one of the best excursions our group has ever done. And we’ve traveled to different islands in the Caribbean and to different locations throughout the world. From the beginning, the Random Wind was communicative and accommodating and allowed us input in the day and offered ideas for where to go. They made us feel welcome and were friendly and open about talking about their experiences and sharing the boat with us. They prepared a delicious lunch and really made sure that we had a good time and stayed safe. I highly recommend this excursion if you’re visiting Saint Maarten
Written 2 March 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Thank you!
Written 7 March 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Jake Kramer
Chicago, IL7 contributions
Dec 2022
We had a group of eight people do a private charter & with Anna & Scotty (& of course, Queenie!). The experience was fantastic. The crew always kept our drinks refreshed & we really felt like they wanted to show us the place they call home!

First to airport beach, & then a lovely bay for a fantastic time in the water, followed up by the BEST snorkeling spot we have ever seen which included a sunken submarine & an underwater crashed helicopter! The fish/wildlife you will see is truly breathtaking.

As avid travelers, we believe this was the best experience we have ever had on an excursion, private or public. Don't forget to give lots of pets to the co-captain, Queenie!
Written 5 December 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Sunshineandsnacks
Danbury, CT12 contributions
Jul 2022 • Family
This was an excellent way to spend a day! What a fun and relaxing adventure. The crew was absolutely wonderful. They make every guest feel special and such there is such an upbeat happy vibe on the boat. The lunch was great and the flow of drinks was constant. The crew even served us while we were in the water. We went snorkeling and just floating around while watching others jump off the Tarzan swing. I felt very safe while in the care of Anna and Captain and Brianna. Thank you for such a special memory our family will have forever!!
Written 14 July 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Mary H
Evansville, IN92 contributions
Jan 2020
If you doing want to be crammed in with tons of other people ..this is the day cruise for you. I had been on their previous sailboat, which evidently is sitting in the bottom of the Lagoon.

The day we sailed (1/23/20) started off cloudy and overcast. It went from bad to worst, with rain (very heavy at times) ALL DAY. In all the years I’ve been coming to St. Maarten, it’s the first time I’ve seen it rain all day.

The crew of 3 remained upbeat, optimistic and of course....keep the passengers lubricated. Head mate Anna was constantly asking if anyone needed anything. Her assistant (whose name I cannot remember) was “Johnny on the spot” to help keep things running smoothly. A lovely fresh lunch was served consisting of grilled chicken, salad, and coconut rice. Packaged cookies were brought out for dessert.

The only negative for me (they couldn’t predict the weather) was I forgot they only go to Mullet Bay and then a little beyond to Cupecoy. Because I’ve always stayed on the Dutch side, the view from the boat was nothing new. Plus, I often go to Mullet Bay Beach on my own. Snorkeling at either of the locations in minimal-you probably won’t see anything! The most fun thing is their trapeze which allows you to swing out and drop into the water.

Be sure to cuddle with Prince ...their boat mascot.
Written 23 January 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Diane S
Sorry you only had a 3 star day. Please don’t tell others that they won’t see anything when everyday they do. The life in all the sea is beautiful, and everywhere unless you can’t see it. But this day is about snorkeling and so much more. Most are able to fully enjoy ALL it has to offer.
Written 24 January 2020
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

FunTravelingGuy
Brentwood, TN39 contributions
The Random Wind catamaran offers an incredible sailing experience in St. Maarten! This experience will be one of the highlights of your trip! The vessel is a beautiful 56' catamaran and very comfortable, with plenty of covered and open public areas for lunging around.

Everything the Random Wind offers is first class, with no corners cut to save cost. This staff goes out of their way to insure you will enjoy your day!

➡️ The service from Anna is unbelievable and very efficient, you will never have an empty drink in your hands. Hats off to her great service!
➡️ Our gourmet lunch was amazing! The grilled curry chicken skewers, with coconut / ginger rice and ceasar salad was the perfect meal, for a day of sailing and snorkeling.
➡️ Capt. Luke was super friendly and his vast nautical expertise made us all feel comfortable...

If you're considering joining a fun day of sun, snorkeling and a beautiful sunset... The Random Wind boat is your perfect choice! Book them in Advance, as they can fill up their tours quickly...
Written 4 January 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Diane S
Thanks so much!
Written 5 January 2021
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Marabeth M
Naperville, IL2 contributions
What a BLAST! We chartered a private day with 16 of us; Lunch and full bar (chicken kabobs/rice/salad); delicious.
The absolute best part is St. Maarten and the spectacular Caribbean Sea 💙
We snorkeled, we played on the Tarzan swing, listened to music and just loved every flipping minute of this excursion. The crew;
the Lovely Anna; Captain Scott and Queenie the catamarans Boss-Dog.
Truly such fun spirit and love for their life and it shows. Cannot recommend them more… a MUST to truly take in this island. Snorkeling spots with a downed helicopter, airplane as well as what one would expect… 🐠🐡🐟🐢 bliss.
Written 10 May 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Jeremy C
1 contribution
Jan 2022
I booked this charter as part of my wedding trip on the best man's 30th birthday. It was our first full day on the island and I could not have asked for a better start to our week. This was one of the best days I've ever had.

Mel, Amanda, and Captain JP were absolutely terrific. The service was amazing and you can tell how much they care about the group having a great time. Our drinks were consistently full and the food was amazing.

The first half of the trip was spent snorkeling in an amazing spot. I was surrounded by a wide variety of tropical fish that felt close enough to touch. During the second half of the trip we anchored near a lovely beach and spent time swimming in the ocean and swinging in off the Tarzan swing.

I cannot recommend Random Wind Charters enough. If you book with them you will not be disappointed.
Written 18 January 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Diane M
Thank you!
Written 29 January 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Conchita122
Puerto Morelos, Mexico8 contributions
Jan 2020
Thanks to the incredibly hospitable and professional Random Wind crew, our research work to collect important scientific data from the submersed Intellireefs by Reef Life Foundation went so smoothly this past January!! Our small team of divers received royal treatment. A spread of delicious healthy food and drinks kept us going on our dives to take video and samples of specialized materials (Oceanite) installed to help regenerate endangered coral reef ecosystems and biodiversity. We ended the day with a sunset sail and rich conversations on deck. I usually get seasick, but the catamaran was stable and so comfortable. Grateful for the generous help with set up in the AM and transporting our gear after a long day...Amazing! It's great to work with kind people and businesses who invest in the well-being of the ocean and want to keep corals and the local economy flourishing in tandem. I look forward to working with Diane and the fun, dedicated team of Random Wind again soon!! THANK YOU !! <3 Colleen Flanigan and Living Sea Sculpture
Written 5 April 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Diane S
Thanks you for all you do. We All Rise Together.
Written 16 April 2020
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

MirjamSaskia
St Martin / St Maarten10 contributions
Apr 2021 • Family
The whole experience from beginning to end was simply perfect. From making the reservations, (super quick response and very accommodating) all the way up to dropping us of at the dock.
Capt. Luke is not only very upbeat and entertaining, he also makes fantastic cocktails. I recommend the « dark and stormy »
First mate Anna is just so sweet and a ray of sunshine! She takes care of the guests like you are rockstars. What separates this boat tour from all the others besides their unique and exhilarating trapeze swing is their first class service in every area! Value for money gets my top rating.
Written 30 April 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Diane M
Thanks so much!
Written 1 May 2021
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Adam R
Pittsburgh, PA11 contributions
This was a perfectly executed day on the water in St. Maarten. Anna and Scott were incredible hosts that made my entire team feel like royalty. From the homemade lunch, to the great mixed drinks, to the island tunes playing the whole day, we couldn’t have enjoyed the trip anymore. If you’re looking for a great excursion for your team or family, look no further!
Written 3 April 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

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*Likely to sell out: Based on Viator’s booking data and information from the provider from the past 30 days, it seems likely this experience will sell out through Viator, a Tripadvisor company.
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2023 Private Sailboat Charter in St Maarten provided by Random Wind