Frequently Asked Questions

• WHERE DOES THE “BOAT LEAVE FROM”?

  
  Both of our classic sailing vessels, Cimarron and Grace, depart daily from Cruz Bay, the adorable main port of St. John in the US Virgin Islands.

  Our standard departure time is 10:00 AM, giving you time for a relaxed morning before your adventure begins. That said, we know every trip is different, so if an earlier start works better for your group, just say the word.

  We're flexible and happy to work with you, contact Captain Rick directly and give him the deets.

  *Guests staying at the Westin St. John can also be picked up directly from the resort.

• WHAT’S INCLUDED IN MY CHARTER?

  The good stuff! Every sail comes with an open bar (because nothing pairs with turquoise water quite like a cold drink in hand) and plenty of snacks to keep everyone happy between dips in the sea.

  For trips in US waters, we can include a stop for lunch or dinner at some truly special spots. Think toes-in-the-sand vibes at Lovango Beach Club, elegant island dining at ZoZo's at Caneel Bay, or the one-of-a-kind experience of Pizza Pi—where a floating pizza boat delivers wood-fired pies straight to you. Yes, really.

  This is your day, your way. Get in touch and let's make it memorable.

• DO WE NEED TO BRING SNORKEL GEAR?

  🤿 Leave it at home! We keep a full selection of masks, snorkels, and fins on board to fit everyone from the littlest adventurers to the tallest. Of course, if you have a trusty mask you love or prescription lenses you rely on, you're welcome to bring your own. Otherwise, just show up ready for an unforgettable day beneath the surface; the sea turtles, colorful fish, and coral reefs are waiting for you.🐟🐠

• DO I NEED MY PASSPORT?

  No passport needed! Our half-day and full-day sails stay within US waters. The US Virgin Islands, (St. Thomas, St. John, Water Island and St. Croix) are an unincorporated territory of the United States, and residents here are American citizens. That means traveling between the USVI and the US mainland is considered domestic travel, just like flying from New York to California. So leave that passport in the safe and just bring yourself, sunscreen, and a sense of adventure.

• WHAT IS THE CANCELLATION POLICY?

  We have a 48-hour cancellation policy. If you need to cancel or reschedule, just let us know at least 48 hours before your sail and we'll work with you.

  ⛈️ Worried about the weather? Don't be! If you've checked the forecast and see rain in the Virgin Islands, know that this is completely normal; brief tropical showers pop up almost daily, but they rarely last long and often make for some of the most beautiful sailing conditions. The truth is, we only cancel for weather about once a year. So unless there's a serious storm, your adventure is on. When in doubt, reach out and we'll give you the real picture.

• DO YOU ACCEPT CREDIT CARDS?

  
  We make paying easy. We accept all major credit cards, cash, Venmo, and checks. Use whatever method is most convenient for you, we just want you focused on enjoying your time on the water.

• WHAT IS THE PRICE OF A CHARTER?

  
  Half-Day Sail - $100/person (morning or afternoon, includes snorkeling)

  Sunset Sail - $100/person (golden hour, cold drinks, no regrets)

  Full-Day Sail - $185/person (lunch + snorkeling + island time)

  Private Charter - $1,300 for up to 6 (your crew, your rules—$185 each beyond 6)

  Luxury Sail - $1,500 (champagne, open bar, fully customized—advance booking required)

  Overnight Sail - $1,400/night, sleeps 4 (captain, first mate, open bar, 1–3 nights or more)