Sailing

Private Luxury Sailing Charters, BYOB & Dolphins

We are a family owned luxury sailing charter business. Come enjoy a BYOB day of sailing and seeing the historic sites of Charleston from the water on one of our sailboats. We offer hourly, daily, or customized tours according to your desires for up to 6 guests maximum (USCG Rules & Regulations). ...

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by the famous Dennis Connor. All trips take place under full sail. We only use our motor to get in and out of Harbour Town.

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos. Learn how to walk and talk like a pirate then climb aboard the Black Dagger and set sail in search of treasure! But wait it's not that easy - You'll need to man the water cannons along the way and ...

Private Morning Sail / Dolphin Tour on Fate, BYOB or Catering

Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht regattas. Fate is not only the most demanded but also the largest and nicest sailing yacht available for Charter in Charleston, known for her beauty under sail, exquisite appointments below deck and ...

Private Hilton Head Sunset Sailing Tour with Dolphin Watching

This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound (North side of island - generally best conditions for sailing). During Sunset, This is generally still pretty breezy with some good sailing. Perfect way to wind down and enjoy the ending of a great ...

Private Afternoon Sailing/Dolphin & History Tours on Mystique

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor since 2012, our sailing yachts are the highest quality and operated by two professional crew to give you the best experience possible. ...

2 Hour Private Dolphin Day Sail

Put your feet up, relax, and learn about the unique Salt Marsh Ecosystem with all of its nature & beauty, and enjoy some of our local history on this day sail! We’ll cut the engine and let the wind do all of the work while you keep an eye out for dolphins and birds!You are welcome to bring any ...

Private Luxury Sunset Cruise on the Sailing Yacht Fate

Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht regattas. Fate is not only the most demanded but also the largest and nicest sailing yacht available for Charter in Charleston, known for her beauty under sail, exquisite appointments below deck and ...

2 - Hour Private Hilton Head Morning Dolphin Watching / Sail

This 2 hour Private Morning Sailing tour, the Captain will take you to Port Royal Sound (North side of the island - generally best conditions for sailing). During the MORNING, this is generally a calm - light wind relaxing sail, a great way to start off the morning or a great day of vacation. The ...