Sailing Trips in Hilton Head Island
Top 5 Best Hilton Head Island Sailing Trips
Found 4 Sailing Trips activities in Hilton Head Island. Sort by Popularity.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 a... More
Likely to Sell Out America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head
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Hilton Head Island
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Superb434 reviews4.6
Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, S....
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... More
Likely to Sell Out Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger
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Hilton Head Island
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Superb634 reviews4.9
The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos.....
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 goo... More
Private Tour
Likely to Sell Out Private Hilton Head Sunset Sailing Tour with Dolphin Watching
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Hilton Head Island
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Superb113 reviews5
This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound ....
Private Tour
2-Hour Private Hilton Head Afternoon Dolphin Watching Sail
This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind for sailing on Hilton Head) on the North side of the island. During the day, this is generally filled with exciting winds for gre... More
Private Tour
Likely to Sell Out 2-Hour Private Hilton Head Afternoon Dolphin Watching Sail
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Hilton Head Island
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Superb113 reviews4.9
This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind....
Private Tour