FAQs

During your unique sailing experience, you will sail, swim, snorkel, eat, drink, and swing into the blue waters of the Caribbean while enjoying:

• Open bar/drinks
• Lunch (full day) and snacks
• Stand-up paddleboard
• All snorkeling equipment
• Awesome stereo for music – yours or ours
• Photos of your day – free online
• No big crowds

Yes — our crew works with first-timers all the time. Quality snorkel gear is provided at no extra charge, and the crew stays close by to help you get comfortable in the water. You won't be handed a mask and pointed toward the ocean — someone will be right there with you.

Absolutely. Life jackets are available for anyone who wants one, and the crew keeps an eye on all guests in the water, not just confident swimmers. You don't need to be a strong swimmer to enjoy snorkeling with us — just tell the crew when you board so they know to check in on you.

We have a great stereo system. We can play the radio and iPods. We have a hook-up for your iPod/phone if you want to bring it, or you can listen to our music – we have a huge selection! We love Jimmy Buffet, Bob Marley, and lots of other artists. On sunset cruises, we typically play soft music (Enya, Mozart, and others.) We have access to thousands of songs but please bring your music to share!

For lunch, your hostess usually makes Caribbean Chicken Skewers with Island-Inspired Rice, Green Salad, and French bread and fruit garnish. If there is a small group or private charter – she may surprise you with something else. We always have cookies and chocolates afterward. Sometimes not everything is available on the island, so things may change.

We would like to know of any serious food allergies and vegetarian, gluten-free musts. While the galley cannot handle making several different meals; it is always best to mention serious food issues when booking. Please do be sure to let us know when booking as we shop for fresh food each morning before we sail.

We have the best boat bar in St. Maarten! Our open bar starts the minute you board and doesn’t stop until you are back on land. We don’t push alcohol on anyone and believe in drinking responsibly, “to enhance the good time we are already having.”

We have cold beer and sodas, vodka, gin, rum, tequila, and many juices and mixers as well as bottled water. Ask for top-shelf at no extra cost. Some say we have the coldest beer in SXM!

Random Wind is a 52 foot extremely stable catamaran; we rarely have seasickness.

We do provide quality snorkel gear and snorkels from the boat. We do not charge extra for snorkel gear.

Yes, there is one available. Anna lives on board with all of the comforts of a floating home which includes two bathrooms or “heads” — one public and one private.

There are steps in the back and a ladder.

Free Cancellation up to 24 hours in advance.

Some days we pick up from Simpson Bay, other days we pick up from Phillipsburg. Please be sure to contact us to confirm your pick-up location.

Simpson Bay Address:

Skipjack's,

Welfare Rd,

Simpson Bay, Sint Maarten

Due to complications at our original pickup location at the Saint Maarten Yacht Club's dock - we are currently unable to pick-up out of this location. Click here for more information.

If arriving by Cruise Ship, the pickup location will be at:

26 Juancho Yrausquin Blvd,

Philipsburg, Sint Maarten

Of course. Our captains are happy to answer questions and walk you through what to expect before we get underway. Random Wind is a stable, well-maintained catamaran, and understanding a bit about how she handles the water often puts nervous guests at ease fast.

Yes. We keep groups small so there's room for everyone, including families. The crew keeps an eye on younger guests in and around the water, and there's plenty for kids to enjoy — the paddleboard, snorkeling, and of course the Tarzan Swing — without it feeling like a crowded or chaotic day for anyone else on board.