Come sail with us today

Sailing Charters on Hilton Head Island, SC



We offer private sailing charters for up to six people. Join us for a beautiful morning sail to start off the perfect vacation day.
-or- be a part of an exciting (generally breezy) afternoon sail and dolphin / wildlife watch.
-or- come celebrate the end of a great day by relaxing and taking in the breath-taking views of Hilton Head’s best sunsets.
Either way, Anchors away sailing charter’s mission is to be a unique part of your visit to Hilton Head Island, giving you a fresh perspective of this beautiful area and possibly introduce you to the wonderful world of sailing.
USCG Licensed Master Captain, Bimini top for shade and comfort, restroom available on board, catering available, Sailing Lessons.

What Sets Us Apart From Other Charters

2 Uniformed Crew
Along with your USCG Licensed Master Captain, A first mate is on every charter to assist with sailing and to cater to our clients needs to maximize their experience
Customer Service and Flexibility, we are available by phone or email to help address any needs or customize your experience. We strive to make every charter a 5 star experience for our clients
We encourage you and your guests to be as involved in the sailing process as you would like. If you are looking for a relaxing, work free experience, we encourage you to kick back and relax while we take care of all of the work!

Weather Statement

It is our job to ensure our groups are SAFE while onboard our vessels. It is also true that we don’t want to disappoint a group who has been looking forward to their sailing experience. A decision to cancel for weather is SOLELY up to the Captains. There is NO NEED to contact us regarding weather. We monitor the weather constantly with several high-end, paid weather subscriptions that aren’t available to the average person. Weather forecasts are made well ahead of the time, and you may have noticed, are often wrong (LOL). Therefore, we make go–no-go decisions based on current conditions, including radar (which we have access to on-board). Weather cancellations are rare. If WE view there is a risk, we will look at delaying the departure time, rescheduling the trip if we both have the ability to reschedule, or canceling the trip and providing a full refund. Our Captains are very experienced, spending 10 hours on the water per day, very concerned about safety and will make the calls we need to make. If you do not hear from us, we are planning to operate, and you should plan to be at the marina 15 minutes prior to your departure time. If we need to get in touch with you, we will do just that! The only thing we ask of our customers is to provide accurate, closely-monitored contact information so we can get in touch with you, if needed.

  • All our charters are very private, for up to 6 people.
  • Water, Coke, Diet Coke and Sprite on board
  • You’re welcome to bring food or beverages in a soft cooler
  • Please no glass containers
  • No Red liquids / Red wine
  • No Spray Sunscreen Please
Sunset Cruises, Hilton Head SC Sail Boat Cruises, Hilton Head SC
Private Sailing Charters
Packages Available
Knot the
Office Vessel

Knot the Office is a beautiful American built Catalina sailing yacht. This is a very comfortable boat both in the cockpit or cabin. Knot the Office has undergone safety inspections by the US Coast Guard and all safety requirements have been met or exceeded.
Knot On Call

Knot on Call (A new option for the 2021 season) is a brand-new Chaparral Suncoast power boat with a 200 hp Outboard. Complete with comfortable seating for up to 6 passengers plus the Captain as well as a small restroom, Sea deck flooring, stereo system, table for dining, a freshwater shower to wash people off after swimming in salt water and blue ambient lighting for after sunset.
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