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Frequently Asked Questions - :


Please read the frequently asked questions before sending us an email. We are very happy to hear your questions, but some are listed below which gives us time to enjoy our kids and cocktails!

Like airplane tickets, trips are sold by many vendors and varying prices. When you book direct, you communicate with the owner. There won't be any misunderstandings about what you book and you won't overpay as we don't add commissions.

Many activities desks here on the island are owned by tour operators themselves and they have been said to lie about other tours in an effort to try to get you to buy their trips. Underhanded and sad, we agree. Always best to book direct and in advance of your arrival so you are sure to get what you want.

We meet at Skipjack’s in Simpson Bay. Skipjack’s is located in the heart of Simpson Bay – right on the lagoon.

If you are coming from the Royal Palm, Atrium, Azure, Flamingo or Simpson Bay Resort and Marina you can walk.

If you are coming from Maho or Cupecoy (Alegria, Royal Islander, Sonesta Maho, The Sapphire, The Cliffs, Rainbow, Ocean Club) – a short drive of 15 minutes or so by car, cab or local $2 bus.

If you are coming from Belair or Philipsburg (Belair Beach Club, Divi Little Bay, Sonesta Great Bay) it should take 20 minutes or so by car, cab or local $2 bus.

From Oyster Pond / Dawn Beach (Oyster Bay Beach Resort, Westin Dawn Beach, Princess Heights) leave 20-30 minutes and there will be no stress.

From Grand Case, Marigot and the cruise ship pier, allow 30 minutes.

Park across the street from Skipjack’s – lots of free parking. Be careful – there can be quite a drop off the road.

9:45AM – We will get there at 9:45 so we can get sailing asap. We DO NOT stress about time and hope that you won’t either – who needs stress on vacation? We do appreciate a phone call – you can use the cab driver’s phone if need be – especially if you are 15 minutes late or more.

Fall through Spring St. Maarten is one hour ahead of Eastern Standard Time

In season (November through May) the draw-bridge over the lagoon entrance opens more frequently and might delay traffic – so best to keep that in mind when planning. If driving and you are early, there is great food at the Taste Factory as well as La Sucriere – two close by bakeries, Taste Factory is just near Skipjack’s and you can park just once. Please wait OUTSIDE the restaurant – they are not open and don’t appreciate us playing with the lobster!!

Bathing suit, towel, sunscreen (NO AEROSOLS / SPRAYS PLEASE), camera, money for your balance and gratuity at your discretion and if you want a souvenir. T-shirts are only $10 and are good quality. Please do not bring snorkel gear unless prescription. We buy top quality and keep it clean.

random wind sailing 400YES! Whenever we can, we have the engine off and really sail. We love to sail! We can usually sail in the morning with no engine as the winds are favorable. It is not possible to sail INTO the wind so we typically motor on the way back as we also have to consider timing. It is not possible to sail without wind.

Typically Caribbean Chicken with rice, salad, French bread and fruit garnish. We usually have cookies and chocolates afterwards. Kids like it too but if yours would really rather have mac and cheese – please let your hostess know BEFORE she cooks lunch. If you have a serious food allergy, please let her know when booking. While she is not a short order cook and cannot accommodate several likes/dislikes/different meals in the small ship’s galley – she does sometimes cook with shrimp, peanuts, etc so please let her know if you have a real and serious food allergy or are vegetarian.

Beer, Coke, Diet Coke, Sprite, bottled water, Rum, Gin, Vodka, Tequila, (top shelf available at no extra cost) ginger ale, club soda, tonic water, juices (usually orange, pineapple, cranberry), margaritas, bloody Marys and of course, RUM PUNCH. We make our own! All subject to availability of course. What would you like to have? Ok to ask.

We schedule to be back by 3PM. If no one has to be anywhere, we may stay out longer if everyone agrees. If there is an accident or traffic or another reason – we will come back a bit early to accommodate those who have evening plans or need to get to the cruise ship terminal.

The S.V. Random Wind is 40,000 pounds and moves through the ocean quite nicely. If the seas are rough – we will reschedule. If you have a tendency, please take something ahead of time. We also have remedies on board; however it is rare that it is needed. We do not offer refunds for seasickness. If you have severe motion sickness, perhaps boats are not for you. Hangovers and boats don’t mix. Best to have a quiet night before sailing then continue the party after sailing for as long as you’d like.

If WE cancel for any reason, we refund your deposit unless you’d like to reschedule. If you cancel, up until one week before your scheduled sail, you will receive a 50% refund of your deposit. If you cancel within a week, we keep your deposit. By making a deposit you are committing to this and when we are full – we turn people away who would also like to join us, so when people cancel or just don’t show, everyone loses.

A phone call or email is necessary. If you are hungover and don’t want to sail – no refund is offered. If you think it is going to rain all day and don’t show up, no refund will be offered. We are better at weather here than you. There are no refunds for no shows. If your ship does not make port – you will receive a full refund.

We take Visa, MasterCard and American Express. We don’t add any extra for using your credit card. (We seriously prefer cash).

credit card and paypal logos

tarzan swing two girls 1 400 1On some boats there is the possibility of flying a giant, beautiful sail called a spinnaker sail. It is large and bulbous. It is used to catch a lot of wind, going downwind (when the wind is coming from behind). We have a spinnaker sail on Random Wind but the ropes run across the boat such that it is not safe to use with more than a few people on board.

There is a big pole that is used to hold the spinnaker sail out to maximize its effectiveness. One day Captain Trevor came up with the idea of using the spinnaker pole to hold out a trapeze from which we can swing. We thought perhaps it was a crazy idea but were interested so next thing we know he has a ski rope and he is pulling the pole down.

After about two months of testing, playing and perfecting, we went public with St. Maarten’s only Tarzan Swing! So now everyday we drop the spinnaker pole about 20 degrees, secure it with two lines, attach an awesome, strong trapeze that Trevor designed and had made and we get up on the rail and swing into the Caribbean blue. We have non-skid tape on the rails for safety.

Now, as a result of Trevor’s instruction, we can throw back flips, back dives and front dives. We play every day bringing great joy to our guests, young and old. The youngest person to do the Tarzan swing is 2 and the oldest is 89!! IF YOUR SHOULDER COMES OUT A LOT OR YOU HAVE ROTATOR CUFF PROBLEMS, THE SWING MAY NOT BE A GOOD IDEA FOR YOU. But it is seriously entertaining watching everyone while sipping your beer or rum punch!

As in any service industry – 15-20% of the total cost is reasonable. It is completely at your discretion but a grand each would be ok with us

Unlike the big boats that can pack on 80+ people for $10-$20 each; our max is 22 and we don’t even like to fill up to that many. We can’t compete with that – so we just do them privately.

We have a radio, CD player and I Pods with over 45,000 songs. Lots of 70s and 80 and now some good new music and tons of reggae. We do steer away from rap and cursing. We are happy to take requests and hook up your iPod as long as the music is cool with everyone.

We imagine that over 300 pounds would be too hard on the equipment. While we have never turned anyone away due to weight, we think 300 pounds is a good limit.

Weather here passes through faster than you can say “SUNSHINE CITY ST. MAARTEN!” Most days when it starts out raining it clears by 10. Please don’t think you can tell if it is going to rain all day because it it raining at 8am. We know the weather patterns here VERY well and will make the call. It’s what we do! We don’t want to sail in the rain either!!

If we are canceling due to weather we will let you know by the same means we have been communicating with you and/or the contact/resort info you have given me. If you cannot reschedule – you will get a refund. That is why it is best to book early in the week if you are staying on island – if we do cancel due to rain – you have a chance to reschedule. Please don’t be a no show. If you don’t show up because you think the weather will not be good and we sail – you will not be given a refund.

It is hard to answer the phone while back-flipping off the Tarzan swing or bowsprit, or zooming around in the dinghy. Also, the phone service here sucks. With email we can respond, make notes, gather and send information and invoices. Also the deposit info and confirmation is sent via email so you have it in writing. We do not take credit cards over the phone as that is dangerous and then your card number is written down. Paypal is secure and we never get your credit card number. If you do have a problem using email / internet then do call.

The dinghy is there to get you to and from the boat before and after the trip and for emergencies. We do not tender you to the beach for these reasons:

It is not safe. There are always swells, even on the calmest days. Taking the dinghy to the beach and having people jump out into the surf and sand is not safe.

While the hostess is cooking, the Captain is watching over his customers, if he takes his attention off of the customers to tender people around; when someone else needs more pertinent attention – he will not be able to help them.

We don’t corral people with the tender like those who take 100 guests; we like to think of you as guests, not cattle. Most often we are so close to the beach that even a non-swimmer can get there easily and safely with a noodle, life-jacket or both.

While we do enjoy the lackadaisical ways of the Caribbean – we never lose sight of safety.

YES our crew is licensed. Captain Trevor is a 200 ton Royal Yachting Association Yacht Master. Equally important as his paper credentials is his experience. You will not find a more capable captain. Diane and April are specifically trained in safety at sea and have many years of boating experience – AND both can carry drinks on a moving vessel without spilling them – THAT is impressive!! Other crew is certified in safety at sea as well.

We all need time off, so there may be other crew on the day you sail.

If your ship is in by 9 and your departure is 4:30 or later – it works! If you are scheduled to leave before 4:30 – email us – we may have others as well and can come back early if need be to accommodate everyone.

 - If it is your birthday or you are on your honeymoon.
 - If we deem you “Tarzan Swinger” of the day.
 - If we play your music all day and no one asks to change it!!
 - If you bring us your leftover food, booze, sunscreen, etc. at the end of the week. We will donate or use for other customers.

NO. We have to make a living. We always give the best deal for you. If you have been given a child discount – you may not use another discount. If you are given the group discount, you will not also get the child discount. Coupons are accepted at time of booking only. You can’t book, giving a deposit, and then try to get a discount when you board the boat.

Coupons are for The Paradise Day Sail only. (Not private charters or sunset cruises.)

Please BOOK DIRECT IF YOU HAVE A DISCOUNT – do not go through the activities desks. We reserve the right to deny discounts through activities desks as they take 20% on top of the discount and we just cannot earn a living that way.

We ask that you consider paying your balance with cash if you have been given a discount, keeps our credit card expenses down. We don’t discount Sunset cruises. Coupons are good for the Paradise Day Sail only.

Thanks in advance for your understanding!

Yes! Quit your whining and get on with it. Anyone can do it! You just need to hold your own weight for a few seconds.

mud 2 400We import spa quality mud for you to slather on. It exfoliates, soothes and draws out dirt and toxins. It is awesome and included in the price!

paddle board 3 400An awesome surf board like thing that you can stand on and paddle around. Many sit and/or kneel as well. It is really fun, you should try it!

Click on the link below and fill out our convenient booking form. 


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2018  Random Wind - Classic Sailing Day Trips on St. Maarten - St. Martin