Private Sailboat Charter in St Maarten
5
Private Sailboat Charter in St Maarten
By Random Wind
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About
Lowest price guaranteeReserve now & pay laterFree cancellation
Ages 0-120
Duration: 5–7 hours
Start time: Check availability
Mobile ticket
Live guide: English
More
- 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
- Start:Multiple meeting point options.
- Option 126 Juancho Yrausquin Blvd, Philipsburg, Sint Maarten
- Option 2Nowhere Special, Welfare Rd, Simpson Bay, Sint Maarten
End:This activity ends back at the meeting 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.
- 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
From
$3,300.00
per group (up to 8)
Select date and travelers
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About the operator
Don’t take it from us – here’s what people have to say about this operator:
- katyhK5565BW0 contributions1000/10 would recommend!Hands down one of the best catamaran experiences I’ve ever had! Anna, Scottie, and sweet Queenie (boat doggo) truly made this experience so great. Anna was super attentive and made it a point to remember everyone’s names. Scottie captained the boat and had interesting knowledge about the island and sailing. Queenie of course was doing queenie things and provided doggo cuddles and some laughs while she had the zoomies as they hoisted the sails. The catamaran was clean, well kept, and even had an area that was shaded which was helpful after I got sunburned the day prior. The Tarzan swing was a hit and a must for all. The area where we went snorkeling was beautiful and full of fish. They also had plenty of noodles and a couple paddle boards to float around on. They served us lunch (chicken skewers, salad, and rice) which was delicious and cooked fresh right on the boat. Also try the rum punch! It was the best rum punch I had the entire trip. Overall it was a great experience and I would highly recommend.Written October 11, 2024
- U7963KTalexv0 contributionsBeam me up Scottie!This excursion was the highlight of our trip to Sint Maarten. A fun filled day of sun, sailing, water activities, food, drinks (all you can handle) and making new friends! Anna is like the bubbles in champagne, so full of energy, high-spirited and she knew everyone's name on the charter! Captain Scottie is the epitome of customer service and has a great arm for tossing a beer 30+ yards! This is a must do trip if you are on the island and guaranteed to have a full belly, drinks galore and fantastic memories!Written October 11, 2024
- Jill S0 contributionsGreat TripStaff was top notch. Fun for the whole family. Snorkeling wasn't great but the experience was so fun. Beautiful views of the island.Written October 8, 2024
- U9016HFcarolinek0 contributionsBest experience ever!!!Best. Experience. Ever. Truly so incredible!!! We had such a fun time, the service was top notch, plenty of food and beverages and the boat is so fun! We Highly recommendWritten October 5, 2024
- Courtles30 contributionsCruise + Queenie = Wonderful ExperienceWould do this excursion again over and over when coming back to SXM. My husband and I checked reviews and thought this one sounded best. Staff and crew and pup (Queenie) did a tremendous job. They learned everyone’s names and were so fun. We did two stops both for water time, snorkeling, or whatever your preference. The second stop we did a Tarzan swing. Food was great and the drinks were even better. Many of the guests did it with their time off a cruise so there IS time for those traveling by cruise. Book this cruise for sure.Written October 5, 2024
- 229debrab0 contributionsBLAST!Had a BLAST! The crew was amazing! The food was amazing! The views were gorgeous! I did this tour alone, but never once did I feel like it!Written September 30, 2024
- Camper526785107400 contributionsRandom Wind is a 10/10 Charter!!! Best Crew!Absolutely wonderful experience with such a lovely crew! I am so happy I got the opportunity to snorkel and sail the beautiful seas around the island. I would recommend this to everyone!Written September 26, 2024
- Shannon1562130 contributionsA great choice!Amazing Day with Anna, Scottie, Mel and Queenie. The crew works hard to please everyone. They immediately remembered each persons name, provided safety instruction, cold drinks, quality food and a day filled with fun. You must try the Tarzan swing.Written August 29, 2024
- Nomad354491297240 contributionsFantastic ExperienceWhat an amazing excursion! I'll admit I was a little hesitant booking from an independent company since we were coming in on a cruise but the reviews were fabulous so we took a chance and it ended up being the best day of our entire cruise. We had 9 people ranging from 7-47 and each one of us had the best time. The crew was so welcoming and took care of our every need. Their boat was fantastic and the areas they took us to for snorkeling were amazing. The lunch was cooked on the boat and was so delicious. We rate this a 10 out of 10 and would definitely book again if we were to go back.Written August 26, 2024
- Jennifer G0 contributionsBest day of my vacationI booked this excursion a couple of months before our cruise and I was looking forward to it since then. It exceeded my expectations. The crew, Anna, Scottie, Mel and Queenie (who, as everyone knows was the one in charge!) made sure everyone was safe, happy and having a great time. Lunch was delicious and no one ever had an empty drink all day long. Diane checked in with me before the excursion to ask about my son’s allergies, which eased my mind. Our party of five all had an awesome day. Wear your sunscreen and a hat!!!Written August 25, 2024
- W9763WNjoshj0 contributionsThe bestMade an account just to review this. Can’t recommend enough. Only thing we’ve done on our long trip where the time flew right by for everybody. We had 4yrs old to 65yrs old in our group and everybody had an absolute blast. The crew is phenomenal, delicious lunch, great drinks, absolutely zero negative things to say. Felt like a lot of experience crammed into one journey. Highlight of a great vacation for sureWritten August 22, 2024
- lindseychafe0 contributions10/10This was one of the best catamarans I’ve ever been on! We booked this separate from the cruise line. They were eye responsive to questions on WhatsApp. The hospitality was unmatched. They never let your drink be empty, made a fantastic lunch, and kept us safe. There was a bad storm that came in and we ended up huddling inside and eating lunch and they all were so welcoming. I can’t say enough about this trip!! Book on their website and you get a discount!Written August 11, 2024
- mommahutch0 contributionsperfect family day.The crew was professional, friendly, and very easy to communicate with. To some it up all of the other 5 star reviews were spot on. My boys love the Tarzan swing. Just book it.Written August 11, 2024
- 417cydneyw0 contributionsThe title of the booking speaks for itself!Ugh! This was truly the best Catamaran experience ever! With a mixture of fun, relaxing and adventurous, the host, the Captain (forgive me, I forgot their names) and Queen the sail pup, were nothing less than hospitable! Definitely a must to book when visiting SXM!Written August 10, 2024
- 994poojab0 contributionsBest day out in Sint MarteenIn all the catamaran day trips we’ve been on around the world, we would have to say that Random Wind would be one of the very best! Anna was a true hostess and made this trip one to remember. We booked this trip for our family, which included 2 young boys under 14, and we all enjoyed it thoroughly - the boys were made to feel very special by all. If you’re looking for a day out in Sint Marteen, I would recommend this trip without a doubt, from the superb views, the delicious and filling lunch, the never ending drinks and the snorkelling, paddle boarding and especially the Tarzan swing! Our son Shay can’t wait to grow up and visit Anna and the crew again!Written August 1, 2024
These reviews are the subjective opinions of Tripadvisor members and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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Popular mentions
5.0
53 reviews
Excellent
52
Very good
0
Average
1
Poor
0
Terrible
0
Mary H
Evansville, IN91 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.
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 January 23, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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 January 24, 2020
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!
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 December 5, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Sunshineandsnacks
Danbury, CT16 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 July 14, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Conchita122
Puerto Morelos, Mexico7 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 April 5, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thanks you for all you do.
We All Rise Together.
Written April 16, 2020
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
James G
1 contribution
Feb 2023
Anna, Captain Scotty and Jackie were as accommodating as they could be. The beer, rum punch and delicious lunch were plentiful and the atmosphere was so relaxing. We snorkeled, swam and used the trapeze to jump off the side of the beautiful boat. The dog, Queenie, was the star of the day. I highly recommend this tour.
Written February 13, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
NCTravelFam
ForsythCounty, NC58 contributions
Mar 2024 • Couples
We thoroughly enjoyed this catamaran ride with lunch. Captain Scottie, Anna, and Jackie were all friendly, and experienced in handling the catamaran and the guests. Having been to St. Maarten before, the snorkeling sights are only mildly interesting to us, it was the atmosphere on the sailboat, the vibe, that made the day. The curried chicken lunch was good, we both enjoyed taking a turn on the swing and watching the other passengers go out and over. The boat ride itself was a delight, the captain making use of the chop to liven-up the afternoon. The whole excursion felt comfortable, safe, and at ease. These folks provide a superior outing, and yes we touched on nirvana
Written April 14, 2024
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Kathryn B
5 contributions
Apr 2023
We had a group of 19 people with kids ranging in age from 7 to 15. Our day spent on the waters of St. Maarten was the best day of our 7 night Caribbean cruise! Arranging this private charger with Diane was simple - she was able to provide comprehensive information and took a small deposit via Venmo. Getting from the cruise port to the marina was a short ~10 minute walk (sidewalk). Once there, Anna got everyone ready to board and quickly went through a safety briefing. Then it was rum punches (or juice/soda) for everyone! The service was impeccable! It was a windy day so they were able to adjust a bit to take us to two areas - the first was for swimming, a beach, or jumping from the boat's jump platform (a huge hit!), followed by a delicious freshly prepared lunch
Written April 20, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
MirjamSaskia
St Martin / St Maarten17 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.
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 April 30, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thanks so much!
Written May 1, 2021
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Marabeth M
Naperville, IL8 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.
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 May 10, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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.
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 January 18, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thank you!
Written January 29, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
No questions have been asked about this experience