Life's too short to stay on land,
Come sail away with us today!

Offering the Newest, Largest, and only
PRIVATE MONOHULL Sailboats on the Island!
Seas The Moment
New Year,
New Yacht!
Available for a great rate for her Inaugural season.

Now Accommodating Groups of various size (call us for details)

Seas the Moment and book Now!

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Dufour Sailing Yacht
Sailing Boat
Sailing Charters
Private Sailing Charters on Hilton Head Island, SC

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What we Offer
We offer private sailing charters for any occasion and for groups of various sizes.

  • Join us for a beautiful morning sail to begin your perfect vacation day. See tons of wildlife and get close to some dolphins along the way.
  • Experience a generally breezy and exciting afternoon sail. Feel free to jump into the action and help handle lines, hoist sails, and steer the boat. It is pretty rare that we go out and do not see any dolphins, so, keep a look out as you never know what we will see out there.
  • Come and celebrate the end of a memorable day with our Sunset Sail or Sunset Powerboat cruise. Typically, great sailing is followed by a relaxing sail back in towards the end of the evening. Often surrounded by wildlife and majestic Hilton Head sunsets. This is a great photo opportunity and a wonderful way to immerse yourself in the beauty this area has to offer.
  • Want a longer experience on the water, no problem. Join us for a half day or a full day away from the dock. These trips are customizable to cater to the experience you desire. Stop and anchor for lunch and a swim, do some ocean sailing or visit a destination. Give us a call to set this trip up.
Whatever experience you choose, Anchors Away Sailing Charter's mission is to be one of the most memorable parts of your visit to Hilton Head Island. We are focused on giving your group a fresh perspective of this beautiful area through the wonderful world of sailing tours.
What Sets Us Apart
  • Our Reputation
    As evidenced by hundreds of five-star reviews from our satisfied guests, Anchors Away Sailing Charters distinguishes itself from the competition by providing unparalleled service from the first point of contact until we bid you farewell at the conclusion of your sailing excursion.
  • Our Service
    We are not a “head boat” operation that packs tons of passengers that you don't know on the boat. The only other individuals besides your family and friends aboard your yacht will be the uniformed Captain and crew member who are committed to personalizing your experience and ensuring you are well cared for.
  • Our Yachts
    Anchors Away Sailing Charters operates a fleet of the newest, best maintained and most luxurious monohull vessels on Hilton Head Island and the surrounding areas. The pride we take in our powerboat and sailing yachts will be evident the moment you step aboard. In addition to all of the required safety equipment, our vessels are equipped with comfortable cockpit cushions, large “bimini tops” for shade, spotless restrooms, and many other amenities to maximize your comfort.
What To Expect
  • Prior to your scheduled departure, you will be greeted by one of our friendly uniformed crewmembers, who will escort you to your vessel and assist you in boarding.

    You will be given a short safety briefing as you get comfortably seated aboard, after which the Captain and First Mate will slip the dock lines and your excursion will begin.

    While motoring out of the harbor, guests may choose to sit in comfortable deck chairs on the bow of the boat. Be sure to watch for dolphins!

    When safely in open water, the crew will raise and trim the sails. The boat may begin to “heal” (lean slightly to one side) as the sails begin to do their work. This is expected and completely safe.
  • And finally, the engine is switched off as the boat continues silently making way on sail power alone. You are sailing!

    Guests are welcome to assist with the sailing as much or as little as they like. The crew will give commentary, take photos, serve drinks, answer questions and do our best to keep you engaged and entertained…or fade into the background to the extent you prefer. Sit back, relax, and enjoy the beauty and serenity of Hilton Head Island on your own terms.

    Near the conclusion of your trip the crew will lower the sails, restart the engine, and make docking preparations. After the boat is safely secured in its slip, the crew will offer to take a picture of your group sitting on the boat, then, will help you to disembark and sincerely thank you for allowing Anchors Away Sailing Charters to help make your day special.
Weather Statement
  • It is our job to ensure your group is SAFE while onboard our vessels. It is also true that we never want to disappoint a group who has been looking forward to their sailing experience. A decision to cancel a charter due to adverse weather is never made lightly but is SOLELY up to the professional discretion of our very experienced Captains.

    We monitor the weather constantly with several advanced weather forecasting and radar products. If we determine there is a risk of unfavorable weather, we may delay the departure time, reschedule the trip if possible, or cancel the trip if absolutely necessary. In the event that we must cancel a charter, we will issue a full refund if we cannot reschedule.
  • If you do not hear from us prior to your trip, we are planning to operate and you should plan to be at the marina 15 minutes prior to your scheduled departure time.

    There is no need to contact us. If we need to contact you regarding a possible interruption, we will contact you at the telephone number provided on the reservation with as much advance notice as possible. However, final decisions regarding weather are often made just prior to departure time. Your safety and comfort are our highest priorities and you can trust us to make prudent decisions and communicate with you appropriately.

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  • Well worth the cost!

    We did the powerboat tour with Captain Paul. Everything about the experience was perfect! Booking was easy, directions were easy to follow, and the boat was clean. Captain Paul was very knowledgeable and we even went for a quick swim off of the boat. Learned about (and saw) dolphins.

  • Sailed Away!

    Such an amazing experience. We had never been on a sailboat before but our captain and first mate were very knowledgeable and made us feel right at home on the water and explained everything in great detail. They even provided history of the island and explained everything around us. It was such an awesome and peaceful experience to enjoy on our honeymoon and would definitely come back!

  • Private Sunset Sail

    I absolutely encourage anyone considering a sunset sail to sign on with Anchors Away! Captain Paul and David provided us an enjoyable and entertaining evening. Their stories of the islands and knowledge of the area and tides made for a fabulous event. The views and wildlife did not disappoint and we came away with every intention of a repeat performance next year! Don't sign on with one of those charters where you're just another passenger; register now for your private sail and make this a memorable trip!

    Carrie H

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