Hilton Head Island


SAILING WORLDWIDE

5 Best Hilton Head Island Tours Worldwide

The best days on the water.

The 5 most popular hilton head island tours. What each sail costs, how long you are on the water, and which crews run it well.

5 Best Hilton Head Island Tours Worldwide

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger - From Harbour Town Pier to the Ship: Getting There Without Stress
Cruises & Boat Tours, Hilton Head Island, Tour Reviews

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

1.Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

A 90-minute Black Dagger pirate cruise on Hilton Head with kid pirate gear, a treasure hunt, and a water-cannon battle with Stinky Pete.

Most Popular★ 5.0

“The staff was outstanding and made the adventure come to life. The kids were so excited and busy the entire time. Definitely recommend!”

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America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head - The 90-minute itinerary: what you actually do during the sail
Cruises & Boat Tours, Hilton Head Island, Luxury Yacht Trips, Sailing, Tour Reviews

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

2.America’s Cup 12-Meter Yacht Afternoon Sail from Hilton Head

A 90-minute sail on Hilton Head’s Stars & Stripes 12-Meter. Help raise sails, enjoy Intracoastal views, and cruise small-group.

★ 4.5

“We had a lot of wind that day, however we went very slow. The sails were not tight, so we weren’t catching the wind. It felt like we were just drifting on the water. Not the sailing experience I expected, especially on a racing sail boat.”

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Parasailing Adventure at the Hilton Head Island - The Boat Setup: Custom Parasail Boat, Back-of-Boat Takeoff
Hilton Head Island, Island-Hopping Sails, Parasailing, Tour Reviews

Parasailing Adventure at the Hilton Head Island

3.Parasailing Adventure at the Hilton Head Island

Parasail over Calibogue Sound from Hilton Head Island with dry or wet options, 8–10 minute flights, possible dolphin sightings, $115.

★ 5.0

“It was a perfect experience, with friendly staff! Very professional, and laid down ground rules. They had a good sense of humor and made sure we had fun.”

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Hilton Head Island: America’s Cup Afternoon Sail - From Harbour Town Pier to the water: timing, parking, and the Sea Pines factor
Cruises & Boat Tours, Hilton Head Island, Island-Hopping Sails, Tour Reviews

Hilton Head Island: America’s Cup Afternoon Sail

Hilton Head Island: America’s Cup Sailing Yacht Cruise - Checking In at Harbour Town: Pier Timing and Resort Fees
Cruises & Boat Tours, Hilton Head Island, Island-Hopping Sails, Luxury Yacht Trips, Sailing, Tour Reviews

Hilton Head Island: America’s Cup Sailing Yacht Cruise

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The sailing ports worth the trip, grouped by the sea they sit on.