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Top Hilton Head Island Sailing

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Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

star-5
435
Embark on a nautical adventure aboard the Black Dagger pirate ship, which transforms kids into little pirates for a treasure hunt on the waters of Hilton Head. The crew provides kids with pirate costumes and pirate lessons before setting sail in search of treasure. This family-friendly cruise has a choice of several departures in the morning and afternoon, making it easy to fit into your schedule.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$35.00
From
$35.00

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head
Likely to Sell OutLikely to Sell Out

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

star-4.5
160
A sailboat cruise from Hilton Head is a peaceful way to see stunning Lowcountry landscapes without the noise of a moor. Join a captain and crew aboard a 39-foot long (12 meter) sailboat that competed in AmericaÔÇÖs CupÔÇöhead through quiet waters and past gorgeous scenery without the roar of a motor. You can even try your hand on deck and help out with the sails.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$52.95
From
$52.95

2.5-Hour Private Hilton Head Afternoon Dolphin Watching Sail

2.5-Hour Private Hilton Head Afternoon Dolphin Watching Sail

star-5
71
Go sailing in Hilton Head Island with this private dolphin-watching tour. Motor out to Port Royal Sound and then put up the sails for a true sailing adventure. Keep an eye out for a variety of wildlife including birds, dolphins, manatees, and sting rays during this boat tour. Maximize time with a private tour and learn about sailing from your guide.
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  • 2 hours 30 minutes
  • Free Cancellation
From
$375.00
per group
From
$375.00
per group

Private Hilton Head Sunset Sailing Tour with Dolphin Watching
Likely to Sell OutLikely to Sell Out

Private Hilton Head Sunset Sailing Tour with Dolphin Watching

star-5
45
This 2.5 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 day. We will take the sails down to peacefully enjoy the beautiful show of an amazing Hilton Head Sunset. After the sun sets, we motor back to the marina and usually dock right around last light for the day. Sunset tours are usually full of wildlife such as dolphins, birds, sting ray and manatee which are some of the great wildlife that are often very prevalent in the evening. You will also have some great scenic views of Hilton Head, Pickney island and Parris island to mention a few. All of our sail trips we encourage our guests to be as involved in the sailing process as they would like. If you would instead like a relaxing trip, we then encourage you to relax and let the crew do the work.
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  • 2 hours 30 minutes
  • Free Cancellation
From
$375.00
per group
From
$375.00
per group

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Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customersÔÇÖ questions.
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